- Effects of substituents on absorption and fluorescence properties of trimethylsilylethynyl- and tert-butylethynyl-pyrenes
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Effects of substituents introduced at 1-position of trimethylsilylethynyl- and tert-butylethynyl-pyrenes on absorption and fluorescence properties were investigated. Fluorescence intensities of 1.0 × 10–5 M CH2Cl2 solutions of these pyrene derivatives were significantly larger than that of pyrene. Absorption of a silyl derivative having a formyl group shifted to longer wavelengths as the solvent polarity increased, whereas that of the carbon analog shifted to shorter wavelengths. On the other hand, in the solvent dependence of fluorescence, both fluorescence of them shifted to longer wavelengths as the polarity of the solvent increased. Fluorescence spectra of pyrene derivatives synthesized in this study at saturated concentrations in CH2Cl2 exhibited excimer emissions in the longer wavelength regions compared to that of unsubstituted pyrene. Fluorescence quantum yields of silicon analogs were higher than that of the corresponding carbon analogs in both solution and solid states. From the results of molecular orbital calculations, it was clarified that the effects of the substituents at the 1-position on the pyrene ring on the absorption and fluorescence properties can be explained by the properties of the molecular orbitals corresponding to the respective electron transitions.
- Furuyama, Taniyuki,Maeda, Hajime,Segi, Masahito,Ueno, Ryota
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- Pyrene-Oxadiazoles for Organic Light-Emitting Diodes: Triplet to Singlet Energy Transfer and Role of Hole-Injection/Hole-Blocking Materials
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Three pyrene-oxadiazole derivatives were synthesized and characterized by optical, electrochemical, thermal, and theoretical investigations to obtain efficient multifunctional organic light emitting diode (OLED) materials. Synthesized molecules were used as emitters and electron transporters in three different device configurations, involving hole-injection/hole-blocking materials that showed good current and power efficiencies. To understand the underlying mechanisms involved in the application of these molecules as emitters and transporters, a detailed photophysical characterization of molecules 4-6 was carried out. The absorption, steady-state fluorescence, phosphorescence, fluorescence lifetime, and phosphorescence lifetime measurements were carried out. The high quantum yield and efficient reverse intersystem crossing leading to delayed fluorescence emission makes the molecule a good emitter, and the charge delocalization properties leading to excimer formation make them efficient electron transporters. Isoenergetic singlet and triplet states of the molecules make the reverse intersystem crossing feasible at room temperature even in the absence of thermal activation.
- Chidirala, Swetha,Ulla, Hidayath,Valaboju, Anusha,Kiran, M. Raveendra,Mohanty, Maneesha Esther,Satyanarayan,Umesh,Bhanuprakash, Kotamarthi,Rao, Vaidya Jayathirtha
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- Novel ethynyl-pyrene substituted phenothiazine based metal free organic dyes in DSSC with 12% conversion efficiency
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Six new dyes based on phenothiazine conjugated to an ethynyl-pyrene moiety are synthesized and characterized. Dye-sensitized solar cells are fabricated using these dyes with and without a co-adsorbent, chenodeoxychloicacid. Simple molecular engineering around the phenothiazine moiety enabled a maximum of 12% photoconversion efficiency with one of the dyes.
- Nagarajan, Bhanumathi,Kushwaha, Suman,Elumalai, Ramachandran,Mandal, Sudip,Ramanujam, Kothandaraman,Raghavachari, Dhamodharan
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- A mechanistically-distinct approach to fluorescence visualization of singlet oxygen
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We describe fluorescence detection of 1O2 by a new strategy. Oxidation of a non-fluorescent sulfoxide by 1O2 occurs via intramolecular oxygen atom transfer in a reactive persulfoxide intermediate. The resulting sulfone shows significantly enhanced (>50-fold) emission. This approach complements known methods, and is being extended to biological 1O2 imaging.
- Yang,Finney
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- 3-pyrenylacrylates: Synthetic, photophysical, theoretical and electrochemical investigations
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The Mizoroki-Heck coupling of 1-bromopyrene with acrylates provides a convenient access to a variety of 3-pyrenylacrylates in very good yields (up to 93%). Their photophysical properties combined with solvatochromic effects were studied. In addition, electrochemical oxidation potentials were determined by DPV (differential pulse voltammetry) measurements. The fine structure of the absorbance spectra obtained from photophysical measurements are compared with the results of theoretical calculations performed by time dependent TD-B3LYP methods using the 6-31G* basis set.
- Reimann, Sebastian,Sharif, Muhammad,Wittler, Kai,Knoepke, Leif R.,Surkus, Annette-E.,Roth, Christian,Ludwig, Ralf,Langer, Peter
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- A pyrene-based dual chemosensor for colorimetric detection of Cu2+ and fluorescent detection of Fe3+
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A pyrene based chemosensor was designed and synthesized. The pyrene fluorophore was connected with a pyridine unit through a Schiff base structure to give the sensor (L). L was tested with a variety of metal ions and exhibited high colorimetric selectivities for Cu2+ and Fe3+ over other ions. Upon binding with Cu2+ or Fe3+, L showed an obvious optical color change from colorless to pink for Cu2+ or orange for Fe3+ over a wide pH range from 3 to 12. Moreover, the fluorescence of L at 370 nm decreased sharply after bonding with Fe3+, while other metal ions including Cu2+ had no apparent interference. Thus, using such single chemosensor, Cu2+ and Fe3+ can be detected independently with high selectivity and sensitivity. The limits of detection toward Cu2+ and Fe3+ were 8.5 and 2.0 μM, respectively. DFT calculation results also proved the formation of stable coordination complexes and the phenomenon of fluorescence quenching by Fe3+. Furthermore, L was also successfully used as a bioimaging reagent for detection of Fe3+ in living cells.
- Guo, Yuxin,Wang, Lei,Zhuo, Jiezhen,Xu, Bo,Li, Xue,Zhang, Jianyu,Zhang, Zhiqiang,Chi, Haijun,Dong, Yan,Lu, Gonghao
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- Pyrene terminal functionalized perylene diimide as non-fullerene acceptors for bulk heterojunction solar cells
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Two perylene diimide (PDI) based small molecules with different terminal groups of pyrene and tert-butyl pyrene, namely P1 and P2, respectively, were designed and synthesized as the acceptor materials in organic solar cells (OSCs). The impacts of the different terminal groups combined with the PDI core on the optical absorption and fluorescence, electrochemical properties, film morphology, and solar cell performance were studied thoroughly. The two compounds possess a broad absorption covering the wavelength range of 400-650 nm and a relatively high LUMO energy level of 3.77 eV. Power conversion efficiency (PCE) of the OSCs based on P2 as the acceptor material and PTB7 as the donor material (1 : 1, w/w) is 0.41%. In contrast, a PCE of 1.35% was achieved for the device based on P1 as the acceptor and PTB7 as the donor (1 : 1, w/w).
- Liu, Xin,Luo, Guoping,Cai, Xinyi,Wu, Hongbin,Su, Shi-Jian,Cao, Yong
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- Pseudo-dumbbell-type molecular beacon probes bearing modified deoxyuridine derivatives and a silylated pyrene as a fluorophore
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We have recently reported a novel pseudo-dumbbell-type molecular beacon probe (Probe 1) possessing polyamine-connected deoxyuridine (U) and silylated pyrene. The probe showed weak fluorescence signal while it stayed alone. Fluorescence signal of the probe was increased in the presence of the complementary DNA. In this study, we prepared new molecular beacons, Probe 2 and Probe 3, possessing the elongated stem portion of Probe 1. In addition, one U in Probe 2 is substituted by anthraquinone-bearing deoxyuridine residue (Y) in Probe 3. Probe 4 is essentially the same as Probe 1 but one deoxyguanosine in the loop portion of Probe 1 is substituted by deoxyinosine in Probe 4. In Probe 5, 3′- terminal deoxycytidine of Probe 3 is substituted by deoxyadenosine. The fluorescence signal of these probes is effectively quenched in the absence of target DNA. Among all, Probe 3 shows the most effective quenching. On the other hand, the signal is substantially increased in the presence of complementary DNA. The ratio of signal to background in case of Probe 3 is the highest. All these probes also recognize single nucleotide alternation in the target DNA to a different extent. The sequence recognition ability of Probe 3 is also the highest among all the probes.
- Chowdhury, Jakir Ahmed,Moriguchi, Tomohisa,Shinozuka, Kazuo
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- The synthesis of polyarene-modified 5-phenyl-2,2'-bipyridines via the methodology and aza-Diels-Alder reaction
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Nucleophilic substitution of hydrogen () in 6-phenyl-3-(2-pyridyl)-1,2,4- triazine under the action of lithium derivatives of polynuclear arenes followed by aza-Diels-Alder reaction with norbornadiene or morpholinocyclopentene gives the novel polyarenemodified photoluminescent 5-phenyl-2,2'-bipyridine ligands.
- Kovalev, Igor S.,Kopchuk, Dmitry S.,Khasanov, Albert F.,Zyryanov, Grigory V.,Rusinov, Vladimir L.,Chupakhin, Oleg N.
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- ON–OFF Fluorescent Imidazole Derivative for Sensitive and Selective Detection of Copper(II) Ions
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A novel multichromophoric hybrid compound, 2-[1-(4-tert-butylphenyl)-4,5-diphenyl-1H-imidazol-2-yl]-6-(pyren-1-yl)quinoline (TDIPQ) has been synthesized as an ON-OFF fluorescent chemosensor for copper(II) ions. Colorless TDIPQ in acetonitrile—water (2:1, v/v) selectively turns yellow along with fluorescence quenching upon addition of copper(II) ions. The fluorescence quenching is directly proportional to the concentration of copper(II) ions. The interaction between TDIPQ and copper(II) was investigated with the aid of UV-Vis, fluorescence, 1H NMR, and MALDI mass spectral techniques. The stoichiometry of the TDIPQ—Cu complex was determined to be 2:1 by Job’s Plot. Under similar experimental conditions, other competitive metal ions had negligible or no interference in the detection ability of TDIPQ. The detection and quantification limits of TDIPQ were estimated at 2 × 10?6 M and 6.2 × 10?6 M. respectively. This method showed an excellent precision of 0.98 ± 0.011 and recovery characteristic of 99.09±1.4%. It is applicable for the quantification of copper(II) in various samples such as drinking water, lab waste water, and soil. A mixture of TDIPQ with the BZA-Co-BZMA polymer can be cast as a film on a glass slide to be used as a sensor device to indicate the presence of copper. Polymer-coated TDIPQ chemosensing property was analyzed by SEM imaging.
- Appalanaidu, E.,Baggi, T. R.,Harsha, K. G.,Rao, B. A.,Rao, V. J.
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- Synthesis and optoelectronic properties of novel organosoluble polynorbornenes containing asymmetric pyrenyl and electroactive substituents via ring-opening metathesis polymerization
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Novel polynorbornenes, poly(NBPYTPA), and poly(HNBPYTPA), containing chromophoric and electroactive groups were synthesized by ring-opening metathesis polymerization using Grubbs' catalysts and followed hydrogenation, respectively. The glass transition temperatures (Tg) of poly(NBPYTPA) and hydrogenated poly(HNBPYTPA) were 195 and 165 °C, respectively. The 10% weight-loss temperatures of hydrogenated poly(HNBPYTPA) and poly(NBPYTPA) were up to 465 and 420 °C, respectively. The photoluminescence emission spectra of poly(HNBPYTPA) showed strong solvatochromic property, revealing that poly(HNBPYTPA) underwent remarkable bathochromic shifts with an increase in solvent polarity. The cyclic voltammogram of poly(HNBPYTPA) film cast onto an indium tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 0.8 and 1.2 V versus Ag/Ag+ in acetonitrile solution. The electrochromic characteristics of poly(HNBPYTPA) showed reversibility, with color changes from yellow to blue and then to red upon the application of potentials from 0 to 1.3 V.
- Lian, Wei-Ren,Ho, Crystal,Huang, Ying-Chi,Liao, Yi-An,Wang, Kun-Li,Liaw, Der-Jang,Lee, Kueir-Rarn,Lai, Juin-Yih
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- Self-Assembly of “Chalcone” Type Push-Pull Dye Molecules into Organic Single Crystalline Microribbons and Rigid Microrods for Vis/NIR Range Photonic Cavity Applications
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A novel supramolecular fluorescent donor–acceptor type dye molecule, (2E,4E)-1-(2-hydroxyphenyl)-5-(pyren-1-yl)penta-2,4-dien-1-one (HPPD) self-assembles in a mixture of ethanol/chloroform through intermolecular π–π stacking (distance ca. 3.384 ?) to form J-aggregated single-crystalline microribbons displaying Fabry–Pèrot (F-P) type visible-range optical resonance. The corresponding borondifluoride dye (HPPD-BF), with a reduced HOMO–LUMO gap, self-assembles into crystalline microrods acting as an F-P type resonator in the near-infrared (NIR) range.
- Vattikunta, Radhika,Venkatakrishnarao, Dasari,Mohiddon, Mahamad Ahamad,Chandrasekar, Rajadurai
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- Bis-selenonium Cations as Bidentate Chalcogen Bond Donors in Catalysis
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Lewis acids are frequently employed in catalysis but they often suffer from high moisture sensitivity. In many reactions, catalysts are deactivated because of the problem that strong Lewis acids also bond to the products. In this research, hydrolytically stable bidentate Lewis acid catalysts derived from selenonium dicationic centers have been developed. The bis-selenonium catalysts are employed in the activation of imine and carbonyl groups in various transformations with good yields and selectivity. Lewis acidity of the bis-selenonium salts was found to be stronger than that of the monoselenonium systems, attributed to the synergistic effect of the two cationic selenonium centers. In addition, the bis-selenonium catalysts are not inhibited by strong bases or moisture.
- He, Xinxin,Wang, Xinyan,Tse, Ying-Lung Steve,Ke, Zhihai,Yeung, Ying-Yeung
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p. 12632 - 12642
(2021/10/21)
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- Method for preparing hydroxypyrene compound with high purity
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The present invention relates to a method for efficiently removing impurities while minimizing yield loss while minimizing yield loss of a hydroxy pyrene compound as a monomer for manufacturing a polymer compound for a hard mask having anti-reflection characteristics used in a lithographic process of a semiconductor manufacturing process. Pulene purification using pyrene (Pyrene) as starting material The present invention relates to a process for producing a high purity 1 -hydroxypyrene and a process for producing 1 -hydroxypyrene by reacting purified pyrene with a halogen compound under an appropriate solvent and catalyst, and a process for purifying 1 -hydroxypyrene.
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Paragraph 0036-0038
(2021/03/16)
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- Naphthoselenodiazole delayed-fluorescence material and preparation method thereof
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The invention belongs to the technical field of photoelectric display devices, and particularly relates to a naphthoselenodiazole delayed-fluorescence material and a preparation method thereof. The naphthoselenodiazole delayed-fluorescence material provided by the invention has a structural formula as shown in a formula (I) which is described in the specification. The invention also provides a preparation method of the naphthoselenodiazole delayed-fluorescence material. The preparation method comprises the following steps: carrying out a substitution reaction on a compound as shown in the formula (II) and a compound as shown in the formula (III) to prepare the compound as shown in the formula (I). The naphthoselenodiazole delayed-fluorescence material and the preparation method thereof provided by the invention solves the technical problems that existing red TADF materials are relatively difficult to synthesize and device efficiency is not high.
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Paragraph 0016-0018
(2021/07/28)
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- Thermally activated delayed fluorescent material and preparation method thereof
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The invention relates to the technical field of electroluminescence, in particular to a thermally activated delayed fluorescent material and a preparation method thereof. The invention provides a thermally activated delayed fluorescent material. The structural formula of the thermally activated delayed fluorescent material is shown as a formula (I). The invention also provides a preparation method of the thermally activated delayed fluorescent material, and the preparation method comprises the following step: carrying out substitution reaction on 2-bromo-7-(pyran-1-yl) anthracene-9, 10-diketone and the compound shown in the formula (II) to prepare the compound shown in the formula (I). The invention provides the thermally activated delayed fluorescent material and the preparation method thereof, and solves the technical problems that the existing red TADF material is relatively difficult to synthesize and the device efficiency is not high.
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Paragraph 0017-0019
(2021/07/31)
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- Pyridylquinoxaline delayed-luminescence derivative and preparation method thereof
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The invention relates to the technical field of photoelectric display devices, in particular to a pyridylquinoxaline delayed-luminescence derivative and a preparation method thereof. The pyridylquinoxaline delayed-luminescence derivative provided by the invention has a structure as shown in a formula (I) which is described in the specification. The invention also provides a preparation method of the pyridylquinoxaline delayed-luminescence derivative. The preparation method comprises the step that a compound as shown in a formula (II) and a compound as shown in a formula (V) are subjected to a substitution reaction to prepare the compound as shown in the formula (I). The pyridylquinoxaline delayed-luminescence derivative and the preparation method thereof provided by the invention solve the technical problems that existing red TADF materials are relatively difficult to synthesize and device efficiency is not high.
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Paragraph 0033-0035
(2021/07/28)
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- Green light-activated delayed fluorescent material and preparation method thereof
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The invention belongs to the technical field of photoelectric display devices, and particularly relates to a green light-activated delayed fluorescent material and a preparation method thereof. The invention provides a green light-activated delayed fluorescent material. The structural formula of the green light-activated delayed fluorescent material is shown as a formula (I). The invention also provides a preparation method of the green light-activated delayed fluorescent material, and the preparation method comprises the step of carrying out substitution reaction on 2-bromo-7-(pyranyl-1-yl)-9H-thioxanthone-9-10, 10-dioxide and the compound shown in the formula (II) to prepare the compound shown in the formula (I). The invention provides the green light thermal activation delayed fluorescence material and the preparation method thereof. The technical problems that an existing green light TADF material is difficult to synthesize, and the device efficiency is not high are solved.
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Paragraph 0019-0021
(2021/07/31)
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- Red light thermal activation delayed fluorescence material and preparation method thereof
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The invention belongs to the technical field of photoelectric display devices, and particularly relates to a red light thermal activation delayed fluorescent material and a preparation method thereof. The invention provides the red light thermal activation delayed fluorescent material. The structural formula of the red light thermal activation delayed fluorescent material is shown as a formula (I). The invention also provides the preparation method of the red light thermal activation delayed fluorescent material. The preparation method comprises the following steps: carrying out substitution reaction on (4-bromophenyl) (phenyl) (4-(pyridine-1-yl) phenyl) phosphine oxide and a compound shown in a formula (II) to prepare a compound shown in the formula (I); the invention provides the red light thermal activation delayed fluorescent material and the preparation method thereof, and solves the technical problems that the existing red TADF material is relatively difficult to synthesize and the device efficiency is not high.
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Paragraph 0013-0015
(2021/08/11)
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- Efficient red delayed fluorescent material and preparation method thereof
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The invention belongs to the technical field of photoelectric display devices, and particularly relates to an efficient red delayed fluorescent material and a preparation method thereof. The invention provides an efficient red delayed fluorescent material. The structural formula of the efficient red delayed fluorescent material is shown as a formula (I). The invention also provides a preparation method of the efficient red delayed fluorescent material. The preparation method comprises the step of reacting tris (4-aminophenyl) amine with a compound shown in the formula (II) to prepare a compound shown in the formula (I). The invention provides the efficient red delayed fluorescent material and the preparation method thereof, and solves the technical problem of low efficiency of the existing TADF micromolecular red light material.
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Paragraph 0021-0023
(2021/08/19)
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- Pyrenyl thiophene derivative and preparation method thereof
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The invention relates to the technical field of photoelectric display devices, in particular to a pyrenyl thiophene derivative and a preparation method thereof. The invention provides the pyrenyl thiophene derivative. The structure of the pyrenyl thiophene derivative is shown as a formula (I). The invention also provides the preparation method of the pyrenyl thiophene derivative, the preparation method comprises the following steps: carrying out substitution reaction on 4-bromo-7-(pyridine-1-yl) benzo [c] [1, 2, 5] thiadiazole and a compound as shown in a formula (II) to prepare the compound as shown in the formula (I); the invention provides the pyrenyl thiophene derivative and the preparation method thereof, and solves the technical problems that the existing red TADF material is relatively difficult to synthesize and the device efficiency is not high.
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Paragraph 0019-0021
(2021/08/07)
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- Delayed fluorescent material for white light device and preparation method thereof
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The invention belongs to the technical field of photoelectric display devices, and particularly relates to a delayed fluorescent material for a white light device and a preparation method thereof. The invention provides a delay fluorescent material for a white light device, which has a structure as shown in a formula (I). The preparation method comprises the following steps: preparing a compound represented by the formula (III) and a compound represented by formula (II) through a reaction; and preparing the compound as shown in the formula (I). The invention provides a delayed fluorescent material for a white light device and a preparation method thereof, and solves the technical problem that an existing white phosphorescent electroluminescent device is low in efficiency.
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Paragraph 0021-0023
(2021/09/01)
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- Heat-activated delayed fluorescent molecule and preparation method thereof
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The invention belongs to the technical field of photoelectric display devices, and particularly relates to a heat-activated delayed fluorescence molecule and a preparation method thereof. The invention provides a heat-activated delayed fluorescent molecule which comprises a compound represented by formula (II) and a compound represented by formula (Suzuki) through I coupling reaction. The invention provides a thermal activation delayed fluorescent molecule and a preparation method thereof, and solves the technical defect of low efficiency of an existing TADF small molecule red light material and an electroluminescent device thereof.
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Paragraph 0024-0026
(2021/09/01)
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- Phosphoric acid delayed-fluorescence material and preparation method thereof
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The invention relates to the technical field of electroluminescence, in particular to a phosphoric acid delayed-fluorescence material and a preparation method thereof. The phosphoric acid delayed-fluorescent material provided by the invention has a structural formula as shown in a formula (I) which is described in the specification. The invention also provides a preparation method of the phosphoric acid delayed-fluorescence material. The preparation method comprises the following step: subjecting a compound as shown in a formula (II) to reacting with a compound as shown in the formula (III) to prepare the compound as shown in the formula (I). The phosphoric acid delayed-fluorescent material and a preparation method thereof provided by the invention solve the technical problems that existing red TADF materials are relatively difficult to synthesize and device efficiency is not high.
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Paragraph 0019-0021
(2021/07/28)
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- Self-assembled interface materials
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In the development of organic electronic devices, how to improve the performance of the devices is a research key point in the art. Among the factors affecting the performance of the devices, interface characteristics between an inorganic material and an organic material are very critical. The inorganic material is subjected to surface modification by using an interface modification material witha matching energy level and good compatibility, so organic/inorganic surface energy and compatibility can be effectively improved, and the transmission capability of interface carriers is improved. According to the invention, pyrene materials having different end groups and having phosphate groups as bonding groups are prepared and bonded to the surfaces of inorganic materials (ITO, Al2O3, perovskite, TiO2 and the like) through a self-assembly method, so monomolecular layers of the pyrene materials are formed; and such interface structure can improve contact between an organic material and aninorganic material and reduce surface energy, and has great application in the field of organic electronic devices.
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Paragraph 0010; 0011
(2020/05/30)
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- O-Annulation to Polycyclic Aromatic Hydrocarbons: A Tale of Optoelectronic Properties from Five- To Seven-Membered Rings
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We take advantage of the Pummerer oxidative annulation reaction to extend PAHs through the formation of an intramolecular C-O bond with a suitable phenol substituent. Depending on the peripheral topology of the PAH precursor (e.g., pyrene, boron-dipyrromethene, or perylene diimide) five-, six-, and seven-membered O-containing rings could be obtained. The effect of the O-annulations on the optoelectronic properties were studied by various methods with the pyrano-annulated pyrene and BODIPY derivatives depicting quantitative emission quantum yields.
- Dordevi?, Luka,Milano, Domenico,Demitri, Nicola,Bonifazi, Davide
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supporting information
p. 4283 - 4288
(2020/06/24)
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- COMPOSITIONS AND METHODS FOR SYNTHESIS OF PHOSPHORYLATED MOLECULES
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The invention provides compositions and methods for synthesis of phosphorylated organic compounds, including nucleoside triphosphates.
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Page/Page column 75
(2019/10/29)
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- Ethynylpyrene Linked Benzocrown Ethers as Fluorescent Sensors for Metal Ions
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Substances containing ethynylpyrenes linked to either one or four benzocrown ethers were synthesized, and their absorption and fluorescence spectroscopic responses to metal ions were assessed. Addition of metal perchlorates to solutions of these substances promotes short wavelength shifts in their absorption and fluorescence maxima and increases in their fluorescence intensities. The magnitudes of the fluorescence intensity increases are dependent on the ring size and number of the crown ether and the nature of the metal cation. Association constants for complex formation were calculated using fluorescence intensity versus concentration data. Analysis using Job's plots showed that the substances containing one benzocrown ether moiety form 1:1 complexes with metal ions. Results of experiments employing repeated addition and removal of Mg(ClO4)2 demonstrate that the ON-OFF fluorescence response can be repeated at least three times. Results of molecular orbital calculations show that complexation with metal ions lowers the energies of both the π and π* levels of the ethynylpyrene moiety and that in some cases the vacant orbital on the metal becomes the LUMO of the complex. An explanation of the spectroscopic changes promoted by metal ions is proposed in terms of electrostatic repulsion and structural regulation.
- Maeda, Hajime,Tanaka, Kazuhiro,Aratani, Mona,Segi, Masahito
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p. 762 - 772
(2019/01/16)
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- Regioselective arene homologation through rhenium-catalyzed deoxygenative aromatization of 7-oxabicyclo[2.2.1]hepta-2,5-dienes
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Combined use of oxorhenium catalysts with triphenyl phosphite as an oxygen acceptor allowed efficient deoxygenative aromatization of oxabicyclic dienes. The reaction proceeded under neutral conditions and was compatible with various functional groups. Combining this deoxygenation with regioselective bromination and trapping of the generated aryne with furan resulted in benzannulative π-extension at the periphery of the PAHs. This enabled direct use of unfunctionalized PAHs for extension of π-conjugation. Iteration of the transformations increased the number of fused-benzene rings one at a time, which has the potential to alter the properties of PAHs by fine-tuning the degree of π-conjugation, shape, and edge topology.
- Murai, Masahito,Ogita, Takuya,Takai, Kazuhiko
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supporting information
p. 2332 - 2335
(2019/02/27)
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- Pyrene-like methylthiopyridyl-2-(2- pyro-) Schiff base (Zn Schiff base) base2+ Preparation and application of fluorescent probe
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The invention relates to the field of a fluorescence probe, and particularly relates to preparation and application of a pyrenes 2-(2-methylthiopyridine)aniline Schiff base Zn fluorescence probe.The probe has the following concrete structure formula shown in the description. The fluorescence probe can be used for recognizing Zn in a methanol solution. The fluorescence probe has the advantages that the excellent selectivity is shown in other ion competition; higher fluorescence sensing property is realized; the detection limit is low; the sensitivity is high; the fluorescent quantum yield is high.
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Paragraph 0043-0047
(2019/12/25)
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- A General Strategy for Through-Bond Energy Transfer Fluorescence Probes Combining Intramolecular Charge Transfer: A Silyl Ether System for Endogenous Peroxynitrite Sensing
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A general strategy is reported for developing through-bond energy transfer (TBET) fluorescence probes by combining intramolecular charge transfer (ICT). The strategy uses a coplanar donor-π-bridge-acceptor system (SiOPh-PyOH) without spirolactam. The off-on switch of TBET and ICT is controlled by coplanar structure changes in the sensing process instead of spirolactam ring-opening in traditional TBET probes. DFT calculations showed that the energy and charge transfers from SiOPh to PyOH are prohibited. Since the SiOPh has no fluorescence, the probe SiOPh-PyOH shows fluorescence properties similar to that of pyrene. After sensing ONOO?, the silyl ether is removed and the probe changes into ?OPh-PyO?. Electron-donating ICT from OPh to PyO? induces a large redshift of emission to 594 nm (179 nm shift). TBET from OPh to PyO? ensures the probe exhibits a large pseudo-Stokes shift of 213 nm. Furthermore, the probe was successfully used in endogenous ONOO? detection. This study offers a new strategy for the construction of TBET probes emitting in the red region without spirolactam ring-opening, a new ONOO? sensing system using silyl ether as a reaction site, and a method for the deprotection of silyl ethers with ONOOH under mild conditions.
- Lu, Gonghao,Guo, Yuxin,Zhuo, Jiezhen,Li, Xue,Chi, Haijun,Zhang, Zhiqiang
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supporting information
p. 16350 - 16357
(2019/11/28)
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- Preparation method of aminopyrene compound
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The invention relates to a preparation method of an aminopyrene compound. The method includes the steps of: in the presence of a copper catalyst and alkali, subjecting a halogen substituted pyrene derivative and tert-butyl carbamate to heating reaction in a mixed solvent of PEG and water to obtain the aminopyrene compound. The raw materials, catalyst and solvent adopted by the invention are cheapand easily available. The method provided by the invention has the advantages of simple operation, high conversion efficiency and easy mass production. The amino protecting group is removed in the Ullmann coupling reaction system in the reaction process, and can be directly converted to aminopyrene without additional protecting group removal step.
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Paragraph 0050-0052
(2019/10/29)
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- Biphenyl compound and application of biphenyl compound to preparation of 1-bromopyrene
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The invention discloses a biphenyl compound and application of the biphenyl compound to preparation of 1-bromopyrene.
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- Applications of Selenonium Cations as Lewis Acids in Organocatalytic Reactions
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The use of trisubstituted selenonium salts as organic Lewis acids in electrophilic halogenation and aldol-type reactions has been developed. The substrate scope is broad. The reaction conditions are mild and compatible with various functionalities. This study opens a new avenue for the development of nonmetallic Lewis acid catalysis.
- He, Xinxin,Wang, Xinyan,Tse, Ying-Lung (Steve),Ke, Zhihai,Yeung, Ying-Yeung
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supporting information
p. 12869 - 12873
(2018/09/14)
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- A pyrene has mercapto ethylamine Schiff base Al3 + Fluorescent probe preparation and application thereof
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The present invention relates to the field of fluorescent probe, in particular to a pyrene has mercapto ethylamine Schiff base Al3 + Preparation and application of the fluorescent probe, specific structural formula as follows: The fluorescent probe can be in CH3 OH - H2 O (95:5, v/v, TRIS 10mmol/L, pH=7.40) solution identification Al3 + , Is: in competition with other ions appear in an excellent selectivity; has high fluorescence sensing nature; and low detection limit; high detection sensitivity, high fluorescence quantum yield.
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Paragraph 0041-0045; 0072; 0073; 0074
(2018/07/30)
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- Naphtho-fluorene carbazole compound and application thereof
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The invention belongs to the field of organic electroluminescence, and in particular relates to a naphtho-fluorene carbazole compound and application thereof. An OLED device manufactured by taking thesynthesized organic compound as a main body light-emitting material can be applied in the fields of AM drive OLED display, PM drive OLED display or OLED illumination. The external quantum efficiency,the power efficiency and the current efficiency of the device are greatly improved, and the service life of the device is obviously prolonged, so that the naphtho-fluorene carbazole compound has thegood market prospect.
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Paragraph 0061; 0064; 0065
(2018/03/26)
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- A [...] derivative and its preparation method and application
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The invention relates to the field of organic electroluminescent materials, and in particular relates to a pyrene derivative as well as a preparation method and application thereof; the pyrene derivative provided by the invention is that large substituent group units having different electronic properties and rigid structures are introduced at the positions of 1-, 3-, 6- and 8- of pyrene; intermolecular phi-phi stacking can be inhibited through molecular coplanar damage; therefore, an exciplex is difficult to form; the crystallization process is inhibited; the film-forming property is improved; therefore, the purpose of improving device properties is achieved; because an electron donor and an electron acceptor are introduced at special positions, a pyrene ring is asymmetrically functionalized; push-pull type molecular is constructed; intramolecular charge transfer is induced to generate; the charge transmission capability of the material is increased; and an organic light-emitting material having blue light property and high fluorescence quantum yield can be prepared. Compared with the existing light-emitting material, the light-emitting efficiency, the colour purity and the stability of the material are greatly improved.
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Paragraph 0078; 0090
(2017/10/13)
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- Method for synthesizing mono-brominated polycyclic aromatic hydrocarbons
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A method for synthesizing mono-brominated polycyclic aromatic hydrocarbons is disclosed. The method comprises the following steps: using polycyclic aromatic hydrocarbon as shown in the formula I as a substrate, adding alkali metal bromide, slowly adding ZnAl-BrO3-LDHs into a mixed solution of water and an organic solvent, reacting at 45-55 DEG C for 5-7 h, and postprocessing a reaction mixture after the reaction so as to obtain mono-brominated polycyclic aromatic hydrocarbon as shown in the formula II. Mass ratio of the polycyclic aromatic hydrocarbon as shown in the formula I to the alkali metal bromide to ZnAl-BrO3-LDHs is 1: 0.6-0.8: 0.7-1.2. The brominating agent is a solid substance, is cheap and easily available, and is environmentally friendly; reaction conditions are mild; postprocessing is convenient, and reaction is simple to operate; utilization rate of atoms is high and selectivity is high; yield of the target product is high, and side reaction is less.
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Paragraph 0020-0038
(2017/12/28)
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- Pyrene boronic acid cyclic ester: A new fast self-recovering mechanoluminescent material at room temperature
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Two pyrene boronic acid cyclic esters, PPB and NPB, were prepared and their solid state fluorescence properties were investigated. Interestingly, the results showed that PPB with a 5-membered ring possessed reversible mechanoluminescence and vapochromic behaviour with a fast self-recovering ability at room temperature, whereas NPB with a 6-membered ring did not. It was demonstrated that the mechanically responsive fluorescence properties of PPB and NPB were highly related to the molecular packing mode and the solid state plasticity.
- Wang, Taisheng,Zhang, Na,Zhang, Ke,Dai, Jingwen,Bai, Wei,Bai, Ruke
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supporting information
p. 9679 - 9682
(2016/08/04)
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- Synergetic effect of CN∧N/C∧N∧N coordination and the arylacetylide ligands on the photophysical properties of cyclometalated platinum complexes
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Six coordinated Pt(II) complexes were prepared, in which the CN∧N or the C∧N∧N ligand were used to form the Pt(II) coordination center. For each coordination profile, three different arylacetylide ligands were used, i.e. naphthalenediimide (NDI), pyrenyl (Py) and naphthaleneimide (NI) acetylides. The electrochemical and the photophysical properties of the complexes were studied with steady-state and time-resolved absorption and emission spectroscopy, cyclic voltammetry and DFT calculations. The photostability and the photoluminescent properties of the complexes are finely tuned by the photoredox and photophysical properties of the arylacetylide ligands and the CN∧N/C∧N∧N Pt(II) coordination center. The triplet excited states of the complexes are an intraligand feature and the lifetime is long (90.1 μs). The photophysical properties of the complexes were rationalized with DFT calculations. The complexes were used as triplet photosensitizer for triplet-triplet annihilation upconversion. The upconversion quantum yield was up to 29.7%. The results are useful for future designing of Pt(II) complexes showing strong visible light-absorption, RT phosphorescence and long-lived triplet excited states.
- Wu, Wenting,Wu, Xueyan,Zhao, Jianzhang,Wu, Mingbo
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supporting information
p. 2291 - 2301
(2015/04/27)
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- Phosphine oxide functionalized pyrenes as efficient blue light emitting multifunctional materials for organic light emitting diodes
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In a search for blue light emitting multifunctional materials, the electron transport enhancing diphenyl phosphine-oxide (Ph2PO) group has been appended to blue light emitting pyrene derivatives. This design, we observe, leads to highly efficient electron transporting blue-emitters for non-doped organic light emitting devices (OLEDs) with good film formation characteristics. The superior performance is attributed to enhanced charge transport and formation of pyrene excimers assisted by thermally activated delayed fluorescence (TADF) in the device. We report the synthesis and characterization using experimental and computational methods of six such pyrene derivatives. Although three of these derivatives show quenching of luminescence in solvents at higher concentrations, in the thin film invariably all six of them exhibit typical pyrene excimer emission. X-ray crystal analysis reveals π-π stacking and the C-H...O interactions in the solid due to the PO group. The measured electron mobilities for all the compounds are higher in comparison to the standard electron transport material, Alq3. Non-doped OLEDs with the pyrene derivatives as emitters (multi-layer configuration) as well as electron transport cum emitters (bilayer configuration) exhibit excellent efficiencies. The derivatives as emitters display a performance with current efficiencies (ηc) in the range 21.1-30.1 cd A-1, power efficiencies (ηp) 11.0-15.76 lm W-1, external quantum efficiencies (EQE) 7.2-9.1% and brightness 28500-42750 cd m-2. In addition, the derivatives as electron transporting emitters demonstrate very good external quantum efficiencies in the range of 3.0-4.0%. These results demonstrate a successful strategy to obtain blue light emitting multifunctional materials for OLED applications.
- Mallesham, Godumala,Swetha, Chidirala,Niveditha, Surukonti,Mohanty, Maneesha Esther,Babu, Nanubolu Jagadeesh,Kumar, Arunandan,Bhanuprakash, Kotamarthi,Rao, Vaidya Jayathirtha
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p. 1208 - 1224
(2015/02/19)
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- Putting corannulene in its place. Reactivity studies comparing corannulene with other aromatic hydrocarbons
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A series of aromatic hydrocarbons were investigated so as to compare the reactivity of corannulene with planar aromatic hydrocarbons. Corannulene was found to be more reactive than benzene, naphthalene and triphenylene to Friedel-Crafts acylation whilst electrophilic aromatic bromination was also used to confirm that triphenylene was less reactive than corannulene and that pyrene, perylene and acenaphthene were more so. The stabilisation of a neighbouring carbocation by the various aromatic systems was investigated through consideration of the rates of methanolysis of a series of benzylic alcohols. The reactivity series was found to parallel that observed for the electrophilic aromatic substitutions and both series are supported by computational studies. As such, a reactivity scale was devised that showed that corannulene was less reactive than would be expected for an aromatic planar species of similar pi electron count.
- George, Stephen R. D.,Frith, Thomas D. H.,Thomas, Donald S.,Harper, Jason B.
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supporting information
p. 9035 - 9041
(2015/09/01)
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- The optical properties and quantum chemical calculations of thienyl and furyl derivatives of pyrene
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A detailed electrochemical, photophysical and theoretical study is presented for various new thienyl and furyl derivatives of pyrene. Their optical properties are described based on UV-VIS absorption and both steady-state and time-resolved fluorescence spectroscopy. DFT and TDDFT calculations are also presented to support experimental data. The calculations results show that HOMO-LUMO orbitals are delocalized uniformly between aromatic core and aryl substituents. Good electrochemical stability of thienyl and furyl hybrids of pyrene confirm their potential application for light emitting electrochemical cells or spintronics mainly due to their beneficial optical and charge transport properties in electrochromic devices. In order to demonstrate this potential, an OLED device is presented. Synthesized compounds included in this OLED device both facilitate electron transport and act as a light emitting layer.
- Idzik, Krzysztof R.,Cywiński, Piotr J.,Kuznik, Wojciech,Frydel, Jaroslaw,Licha, Tobias,Ratajczyk, Tomasz
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p. 22758 - 22769
(2015/09/07)
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- SULFUR CHELATED RUTHENIUM COMPOUNDS USEFUL AS OLEFIN METATHESIS CATALYSTS
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Sulfur chelated ruthenium compounds represented by the following formula: wherein M indicates the ruthenium metal bound to a benzylidene carbon; R represents C1-C7 alkyl group or optionally substituted aryl; X1 and X2 each independently represent halogen; Y1 and Y2 each independently denote unsubstituted or alkyl-substituted phenyl; and Z independently represents hydrogen, electron withdrawing or electron donating substituent, with m being an integer from 1 to 4, and processes and compositions related thereto.
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Paragraph 0084
(2014/06/23)
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- Furyl derivatives of pyrene: Efficient synthesis and relevant optical properties
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A series of various furyl derivatives of pyrene were synthesized by Stille cross-coupling procedure. Their structures were characterized by nuclear magnetic resonance, and elemental analysis. Optical properties of the synthesized materials as well as their energy levels were investigated by ultraviolet-visible absorption supported by fluorescence spectra. All of the studied compounds exhibit fluorescence with energy peaks dependent on the number of furyl substituents. Furthermore, quantum mechanical modeling method of obtained materials are studied. Experimental data are focused on quantum chemical calculations. Highest occupied molecular and lowest unoccupied molecular orbitals are delocalized uniformly on both pyrene core and furyl substituents. Furanyl-pyrene hybrids are potentially good materials for optical applications mainly due to their optical and charge transport properties, which are also desired for electronic applications.
- Idzik, Krzysztof R.,Ledwon, Przemyslaw,Licha, Tobias,Kuznik, Wojciech,Lapkowski, Mieczyslaw,Frydel, Jaroslaw
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- Synthesis and optical properties of various thienyl derivatives of pyrene
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A series of various thienyl derivatives of pyrene were synthesized by Stille cross-coupling procedure. Their structures were characterized by 1H NMR, 13C NMR and elemental analysis. The spectroscopic characteristics were investigated by UV-vis absorption and fluorescence spectra. Based on quantum chemical calculations, the energy levels of investigated molecules with respect to the pyrene molecule were also discussed.
- Idzik, Krzysztof R.,Licha, Tobias,Lukes, Vladimir,Rapta, Peter,Frydel, Jaroslaw,Schaffer, Mario,Taeuscher, Eric,Beckert, Rainer,Dunsch, Lothar
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p. 153 - 160
(2014/03/21)
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- Synthesis, structure, and opto-electronic properties of regioisomeric pyrene-thienoacenes
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Three regioisomeric sulfur-bridged pyrene-thienoacenes (PTAs) have been synthesized. The crystal structures and optoelectronic properties of these ring-fused PTAs and their ring-opened precursors have been fully investigated. Among these isomers, the [3,4]-extended compound (4-S-PTA) shows the most pronounced spectral red-shift and highest quantum yield as well as large transistor mobility.
- Zhang, Shiqian,Qiao, Xiaolan,Chen, Ying,Wang, Yuanyuan,Edkins, Robert M.,Liu, Zhiqiang,Li, Hongxiang,Fang, Qi
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p. 342 - 345
(2014/04/03)
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- Sulfoxides as response elements for fluorescent chemosensors
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Sulfoxides are shown to be viable reporting groups for fluorescent chemosensor development. Metal coordination of sulfoxide-appended fluorophores suppresses excited-state pyramidal inversion of the sulfoxide, leading to enhanced fluorescence emission. This new structural motif allows the construction of fluorescent chemosensors that do not require nitrogen coordination as part of the signaling process, that have a range of selectivities and affinities for oxophilic metal ions, and that can function in water.
- Kathayat, Rahul S.,Finney, Nathaniel S.
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supporting information
p. 12612 - 12614
(2013/09/23)
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- Synthesis, structural and spectral properties of diarylamino-functionalized pyrene derivatives via Buchwald-Hartwig amination reaction
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A new series of diarylamino-functionalized pyrene derivatives, namely, 1-(N,N-diarylamino)-substituted pyrenes (7), isomer of 1,6-bis- and 1,8-bis(N,N-diarylamino)-substituted pyrenes (8/9) and 1,3,6,8-tetrakis(N,N- diarylamino)-substituted pyrenes (10) have been synthesized. The structures of these synthesized compounds were determined on the basis of spectral data and elemental analysis. All compounds 7-10 have bright fluorescent emissions from sky-blue to green in solution condition (λmax = 464-500 nm in CH2Cl2) and high emission efficiency (Φf = 0.84-0.96 in dichloromethane). All compounds have high thermal stability and good solubility in common organic solvents. The electronic properties of these compounds were determined by spectroscopic methods such as UV-vis absorption spectroscopy and fluorescence emission spectroscopy. Clear evidences were obtained that the longest wavelength bands of these compounds are bathochromically red-shifted as the number of the diarylamino-substituent increased.
- Hu, Jian-Yong,Feng, Xing,Seto, Nobuyuki,Do, Jung-Hee,Zeng, Xi,Tao, Zhu,Yamato, Takehiko
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