38303-35-4Relevant articles and documents
Synthesis and spectral properties of a hexameric pyrene-fluorene chromophore based on cyclotriphosphazene
Alida?i, Hüsnüye Ardi?,?o?ut, Bünyemin,Kili?, Adem,Ye?ilot, Serkan
, p. 436 - 441 (2014)
A new fluorene substituted methoxybenzene-pyrene chromophore (3), [1-(9,9-dimethylfluorene)-8-(4-methoxyphenyl)]pyrene, was synthesized by the Suzuki cross-coupling reactions of 1,8-dibromopyrene with 4-methoxyphenylboronic acid and 9,9-dimethylfluorene-2-boronic acid pinacol ester, respectively. The hexameric compound (5), hexakis{1-oxyphenyl-8-(9,9-dimethylfluorene)pyrene} cyclotriphosphazene, was prepared by a nucleophilic displacement reaction of hexachlorocyclotriphosphazene, N3P3Cl6, with (4), [1-(9,9-dimethylfluorene)-8-(4-hydroxyphenyl)]pyrene, which was obtained from the deprotection of compound (3). The newly synthesized compounds were fully characterized by standard spectroscopic techniques. The spectral properties of compound (5) were investigated by thermogravimetric analysis, differential scanning calorimetry, UV-Vis and fluorescence spectroscopy, and cyclic voltammetry. In addition, fluorescence quantum yields, fluorescence lifetimes and fluorescence quenching behavior by 1,4-benzoquinone were investigated in dichloromethane. It was found that the hexameric compound (5) emitted in the blue-light spectral region with a maxima of 455 nm, with a quantum yield of 0.63 in dichloromethane. Compound (5) was amorphous in nature and exhibited excellent thermal stability, with a decomposition temperature of 498 °C and a high glass-transition temperature of 58°C.
Constitutional isomers of dendrimer-like pyrene substituted cyclotriphosphazenes: Synthesis, theoretical calculations, and use as fluorescence receptors for the detection of explosive nitroaromatics
Ardic Alidagi, Husniye,Tümay, Süreyya O?uz,?enocak, Ahmet,?iftbudak, ?mer Faruk,?o?ut, Bünyemin,Ye?ilot, Serkan
, p. 16738 - 16747 (2019)
Two constitutionally isomeric bis-pyrenyl phenol dendrons (4 and 6) and their dendrimer-like cyclotriphosphazene derivatives (5 and 7) with different architectural motifs on the periphery of the cyclotriphosphazene ring are designed and synthesized, and their structural characterization is carried out using standard spectroscopic techniques (elemental analysis, 1H, 31P and 13C NMR spectroscopies and MALDI-TOF mass spectrometry). The thermal and photophysical properties of these newly synthesized compounds are also investigated. The geometric optimization of the constitutional isomeric dendrons and their dendrimer-like derivatives, HOMO-LUMO energy levels and molecular interactions are performed using density functional theory calculations at the wB97XD/6-31G(d) level. The fluorescence detection behaviors of 5 and 7 are evaluated for nitro aromatic compounds (NACs). Results of measurements show that explosive nitroaromatics efficiently quenched fluorescence emission, whereas other tested competitive species (toluene, RDX, picric acid, benzene and 20 metal ions) induced no spectral changes, suggesting that these dendrimer-like cyclotriphosphazene derivatives (5 and 7) could be promising candidates to be applied as sensors for explosive nitro aromatics with high selectivity and sensitivity.
Electron-Transfer-Induced Self-Assembly of a Molecular Tweezer Platform
Thakur, Khushabu,Wang, Denan,Mirzaei, Saber,Rathore, Rajendra
supporting information, p. 14085 - 14089 (2020/10/12)
The design and synthesis of a new molecular tweezer (T-tmp) with electron-rich pincers are reported. The stable monocationic radicals and self-assembled dimeric radicals of this molecular tweezer platform were prepared by chemical oxidative titration. With the aid of DFT calculations, it was found that the dimeric radicals with syn-syn-syn conformer has the most stable structure, with the hole primarily delocalized between parallel stacked pyrenyl groups.
Synthetic method for preparing novel pyrene D-pi-A type solar cell dye through click reaction
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Paragraph 0040; 0046; 0056; 0066; 0076; 0086; 0096; 0106, (2020/10/20)
The invention provides a synthetic method for preparing a novel pyrene D-pi-A type solar cell dye through a click reaction, and belongs to the field of organic photoelectric material synthesis. The click reaction principle is utilized, pyrene compounds are used as elements; alkyl is introduced through an azido-alkynyl Husigen cycloaddition reaction catalyzed by copper; a Sonogashira coupling reaction is performed to inoculate a benzoic acid or cyanoacrylic acid-like receptor; a branched chain is introduced to a pyrene element to form the D-pi-A type solar cell dye material. According to the technical route, by controlling the positions of electron donating/withdrawing groups, the problems of low efficiency and the like caused by aggregation of dye molecules can be solved so that the compound has very high ultraviolet absorption and photoelectric conversion efficiency. In the synthesis process, the ultraviolet, laser and microwave integrated technology is beneficial to promoting click reaction to be accelerated, and a new thought and a new scheme are provided for rapid control synthesis of pyrene D-pi-A type solar cell dyes and similar compounds.
Pyrene derivatives with two types of substituents at positions 1, 3, 6, and 8-fad or necessity?
Zych, Dawid,Slodek, Aneta
, p. 24015 - 24024 (2019/08/13)
1,3,6,8-Tetrasubstituted pyrene derivatives with two types of substituents in an asymmetry or axial symmetry pattern have been prepared and characterized. To the best of our knowledge, these compounds are compared for the first time to their analogs containing the same substituent at all four positions, which explains the need for their synthesis. We present information on the chemistry of pyrenes, which are substituted in the non-K region, to help obtain the most efficient materials. Moreover, theoretical studies were extended to analogs which contain the first type of substituent at positions 1 and 3, whereas the second type of substituent is located at positions 6 and 8, for which the synthesis is nontrivial. The obtained data show which trend these kinds of molecules will follow.
Highly efficient pyrene blue emitters for OLEDs based on substitution position effect
Jung, Mina,Lee, Jaehyun,Jung, Hyocheol,Kang, Seokwoo,Wakamiya, Atsushi,Park, Jongwook
, p. 42 - 49 (2018/05/24)
To investigate the effect of substitution position of the side group on a pyrene core, three derivatives having a triphenylbenzene group as a bulky side group at the 1,6-position, 4,9-position, and 1,8-position were successfully synthesized: 1,6-bis(5′-phenyl-[1,1':3′,1″-terphenyl]-4-yl)pyrene (1,6-DTBP), 4,9-bis(5′-phenyl-[1,1':3′,1″-terphenyl]-4-yl)pyrene (4,9-DTBP), and 1,8-bis(5′-phenyl-[1,1':3′,1″-terphenyl]-4-yl)pyrene (1,8-DTBP). The three synthesized materials showed excellent thermal stability with a high Tg of >140 °C and a high Td of >500 °C. Due to the highly twisted structure of 1,8-DTBP in the film state, the absolute photoluminescence quantum yield value was improved. Of the three synthesized materials used as an emitter in a non-doped organic light-emitting diode device, 1,8-DTBP showed highly efficient electroluminescence performance, with a luminance efficiency of 6.89 cd/A, power efficiency of 3.03 lm/W, and external quantum efficiency of 7.10% at 10 mA/cm2. In addition, 4,9-DTBP showed a deep-blue emission of CIE x, y (0.158, 0.063) suitable for HD-TV.
Preparation of a hyperbranched porous polymer and its sensing performance for nitroaromatics
Wu, Hongtao,Xu, He,Tao, Furong,Su, Xi,Yu, William W.,Li, Tianduo,Cui, Yuezhi
, p. 12802 - 12810 (2018/08/04)
A hyperbranched porous polymer P based on adamantane and pyrene was synthesized through the Sonogashira coupling reaction. The three-dimensional rigid molecular skeleton of adamantane makes polymer P porous. Compound M, which acts as the block moiety between two adamantane groups in polymer P, was also synthesized for the control experiment. Compared with M, the characteristics of P changed remarkably with it exhibiting different emission behaviors and performances for the detection of DNT. In saturated DNT vapor, the quenching efficiency (ηEP) of film P (82%) was remarkably superior compared with that of film M (22%). In addition, a series of films with different thicknesses and different amounts of polymer P were prepared. Results showed that the quenching efficiencies did not change with an increase in the film thickness.
1,8-Substituted Pyrene Derivatives for High-Performance Organic Field-Effect Transistors
Gong, Xiaojie,Zheng, Chaoyue,Feng, Xingcui,Huan, Yihong,Li, Jiewei,Yi, Mingdong,Fu, Zhenqian,Huang, Wei,Gao, Deqing
, p. 3920 - 3927 (2018/11/23)
There have been many reports on the application of pyrene derivatives as organic semiconductors, but 1,8-subsituted pyrene semiconductors are less well-developed. Two p-type 1,8-substituted pyrene derivatives were synthesized that were composed of a pyrene core, thiophene or bithiophene arms, and end-capped octyl chains. These structures were not completely symmetrical and the dihedral angles between the pyrene core and the adjacent thiophene units had a difference of approximately two degrees. The field-effect performance of these materials was tested on a variety of dielectric surfaces. The performance of both materials with a spin-coated polystyrene layer on SiO2 (PS-treated SiO2) was better than that with an octadecyltrichlorosilane self-assembled monolayer on SiO2 (OTS-treated SiO2), which was mainly attributed to the presence of large grains on the low-leakage and high-capacitance PS films. The thiophene-contained compound presented a hole mobility of up to 0.18 cm2 V?1 s?1 on PS-treated SiO2, which was 45 times that of the bithiophene-contained compound, owing to less steric hindrance, high crystallinity, and large grain size.
Biphenyl compound and application thereof in preparation of 1,8-dibromopyrene
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, (2018/10/11)
A biphenyl compound and an application thereof in preparation of 1,8-dibromopyrene are disclosed.
A new series of short axially symmetrically and asymmetrically 1,3,6,8-tetrasubstituted pyrenes with two types of substituents: Syntheses, structures, photophysical properties and electroluminescence
Zhang, Ran,Zhang, Tengfei,Xu, Lu,Han, Fangfang,Zhao, Yun,Ni, Zhonghai
, p. 237 - 246 (2016/08/04)
A new series of short axially symmetrically (4a and 4b) and asymmetrically (4c and 4d) 1,3,6,8-tetrasubstituted pyrene-based compounds with two phenyl moieties and two diphenylamine units on the pyrene core were designed and synthesized based on stepwise synthetic strategy. These compounds were structurally characterized and their photoelectric properties were investigated by spectroscopy, electrochemical and theoretical studies. The structures of 4a and 4b were determined by single-crystal X-ray diffraction analysis, indicating that the compounds are twisted by the peripheral substituents and the intermolecular π-π interactions have been efficiently interrupted. The four compounds exhibit high absolute fluorescence quantum yields (ФF) in dichloromethane (83.31–88.45%) and moderate ФFs in film states (20.78–38.68%). In addition, compounds 4a and 4b display relatively higher absolute ФFs than those of 4c and 4d in film states. All the compounds exhibit high thermal stability with decomposition temperatures above 358?°C and the values of 4c and 4d are higher than 4a and 4b. Compounds 4a and 4b can form morphologically stable amorphous thin films with Tg values of 146?°C and 149?°C, respectively. However, there are no obvious Tg observed in compounds 4c and 4d. Electroluminescent devices using 4a and 4b as doped emission layer show promising device performance with low turn-on voltage (3.0?V), maximum brightness around 15100?cd/m2 and 16100?cd/m2, maximum luminance efficiency of 12.4?cd/A and 13.6?cd/A and maximum external quantum efficiency of 5.34% and 5.63%, respectively.
