56765-79-8Relevant articles and documents
Azo-coupled zinc phthalocyanines: Towards broad absorption and application in dye-sensitized solar cells
Han, Mingliang,Zhang, Xuejun,Zhang, Xiaoxia,Liao, Chaoqiang,Zhu, Baiqing,Li, Qiaoling
, p. 864 - 873 (2015)
The synthesis of symmetrical azo-coupled zinc phthalocyanines (7, 8, 10 and 11) incorporating two spectrally complementary photogenerators (azo dyes and phthalocyanines) by NN double bonds in a single structure was described. The four sensitizers were fully characterized by Fourier Transform infrared spectroscopy, UV-Vis spectroscopy, proton nuclear magnetic resonance, mass spectrometry, elemental analyses, thermogravimetric analysis and cyclic voltammetry. All the azo-coupled phthalocyanines exhibited broad absorptions covering the range 300-800 nm. The cyclic voltammetry studies indicated that the LUMO and HOMO energy levels of four synthesized azo-coupled phthalocyanines could ensure efficient electron injection and thermodynamically favorable dye regeneration. Thermal stability studies showed that the four sensitizers were stable above 200 °C. The new compounds were tested in dye-sensitized solar cells and compound 8 showed the best photovoltaic performance, yielding 2.7% power conversion efficiency.
Bio-inspired domino reduction of nitroarenes by acrolein-amine conjugates in one-pot operation
Takamatsu, Masayuki,Fukase, Koichi,Tanaka, Katsunori
, p. 811 - 813 (2017)
Biologically relevant amines react with acrolein to provide 3-formyl-3,4-dehydropiperidine (FDP) as the oxidative stress product, which has reduction potential via hydrogen transfer. This biogenic process was applied to the domino reduction of electron-deficient nitroarenes in one-pot operation, by simply mixing primary amine, acrolein, nitroarene, and calcium chloride. The reaction can be performed in a gram-scale without the use of hazardous metals.
The new ball-type zinc phthalocyanine with S[sbnd]S bridge; Synthesis, computational and photophysicochemical properties
Bilgi?li, Ahmet T.,Gen? Bilgi?li, Hayriye,Günsel, Arma?an,Pi?kin, Hasan,Tüzün, Burak,Nilüfer Yarasir,Zengin, Mustafa
, (2020)
In this study, the starting compound 4,4′-disulfanediyldiphthalonitrile (1) and its ball-type zinc phthalocyanine (2) were synthesized and characterized by standard spectroscopic methods. The molecular structure and supramolecular dynamics of the compound (1) have been investigated by the analysis of the single crystal X-ray diffraction data. To further understand the intermolecular interactions of compound (1), the Hirshfeld surface analysis has been carried out. The compound (1) and (2) were investigated by quantum chemical calculations. Their quantum chemical parameters such as highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO), chemical hardness were performed by B3lyp, HF, M062x method. The ΔG values of the compound (1) and (2) were calculated by using the obtained results. The calculated Infrared spectroscopy, Nuclear Magnetic Resonance, and UV–vis spectra of the compounds were investigated. In addition, photophysical (fluorescence quantum yields) and photochemical (singlet oxygen generation and photodegradation under light irradiation) properties of newly synthesized ball-type zinc phthalocyanine (2) were investigated in dimethyl sulfoxide (DMSO) solutions. We obtained very high singlet oxygen quantum yields as 0.89, suggesting its potential as photosensitizer in PDT treatment.
Supramolecular subphthalocyanine complexes-cellular uptake and phototoxicity
Dubbert, Justin,H?ing, Alexander,Knauer, Shirley K.,Riek, Nathalie,Voskuhl, Jens
, p. 7653 - 7656 (2020)
In this communication we report on the synthesis and application of axially functionalized boron-subphthalocyanines (SubPC) which are able to form host-guest complexes with cyclodextrins. Here, a tert-butylphenyl substituted SubPC was investigated concerning its complexation with β-cyclodextrin (β-CD) and a β-cyclodextrin polymer. NMR-titrations showed the formation of a 1: 1 complex with β-CD. These assemblies were analyzed for their cellular distribution as well as their phototoxicity towards HeLa cells.
Axial and peripheral tetraarylethylene-modified subphthalocyanines with distinctive fluorescent performances
Ding, Wei,Yan, Liying,Cao, Fei,Luo, Qianfu
supporting information, (2021/05/06)
Special aromatic structure and unique geometric characteristics make subphthalocyanines possess distinctive electronic structures and physicochemical properties. In this paper, tetraarylethylenes with aggregation-induced emission were introduced to subphthalocyanine macrocycles at the axial direction and the periphery to improve the fluorescence emission properties. Results show that the modification at the two different positions of the subphthalocyanines has different effects on regulating the fluorescence performances. The subphthalocyanine modified axially by tetraphenylethylene shows outstanding fluorescence resonance energy transfer (FRET) phenomenon, and the modification on the periphery of subphthalocyanine is conducive to enhance the fluorescence intensity. These distinctive performances have the potential applications in fluorescence sensor and probe.
Porphyrin phthalocyanine covalent bifunctional graphene nonlinear nano hybrid material and preparation method thereof
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Paragraph 0048; 0053; 0054, (2021/10/02)
The invention relates to a porphyrin phthalocyanine covalent bifunctional graphene nonlinear nanometer hybrid material and a preparation method thereof. The electron porphyrin and the electron-withdrawing phthalocyanine with the strong electron group are bonded to the surface of the graphene through radical addition reaction, charge is obtained through bridging of graphene, and third-order nonlinear performance of the organic - inorganic hybrid material is enhanced. In the invention, amino-substituted tetraphenylporphyrin and amino-substituted pull electron phthalocyanine are reacted through azo salt, so that a novel bifunctional organic-inorganic covalent functionalized nano hybrid material is successfully prepared. , The prepared material has more enhanced nonlinear optical performance in the nanosecond visible light field compared with the traditional materials, and has very strong reference significance.
Preparation method of diamine containing phthalonitrile group
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Paragraph 0018-0019; 0024-0025; 0030-0031; 0036-0037; ...., (2021/11/14)
The invention relates to a preparation method of a diamine containing phthalonitrile group. , 4 - Aminophthalonitrile is prepared from 4 -nitrophthalonitrile by reducing the nitro group, then a phthalonitrile group-containing dinitro compound is prepared by reaction of benzoquinone containing phthalonitrile group, and the dinitro compound containing phthalonitrile group is obtained through reaction of the dihydric phenol with 4 - 4 -nitrofluorobenzene. The method can be used for preparing binary amines containing phthalonitrile groups on a scale. The product is single. When the overall conversion rate reaches 50% or more, a phthalonitrile group-containing diamine having a high purity 90% or more can be obtained. The method is simple in production operation and low in equipment requirement.
A high-performance photoelectrochemical sensor for the specific detection of H2O2and glucose based on an organic conjugated microporous polymer
Chen, Yanli,Gao, Wen,Kong, Xia,Li, Xiyou,Liu, Qi,Liu, Xue,Shen, Jingshun,Sun, Qiqi,Xing, Chuanwang,Zhang, Yuexing
supporting information, p. 26216 - 26225 (2021/12/13)
Cathodic photoelectrochemical (PEC) biosensors are one of ideal systems for sensing applications owing to their advantages in the low-cost, simplicity of the detection and miniaturization of the sensors with high sensitivity and specificity. Herein, a high-performance PEC sensor based on a 2D porphyrin-phthalocyanine conjugated microporous polymer (PorPc-CMP) is reported for the specific detection of H2O2 and glucose in the wide linear ranges of 0.05-100 and 0.05-5000 μM with an ultra-low limit of detection (LOD) of 13 and 27 nM, respectively. All of them achieved the best levels, when compared to H2O2 and glucose tetrapyrrole-based photoelectrochemical sensors reported so far. After a comparative analysis on the morphology, optical-electrical properties and partial charge density plots by DFT calculations for the PorPc-CMP and its analogues (PorPor-CMP and PcPc-CMP), it is revealed that the high PEC-sensing performance of PorPc-CMP is largely related to the synergistic effect of unique multi-channel D-A structure and elaborate hollow tube-like morphology, which leads to the effective charge separation, enhanced charge transportability and high utilization of light irradiation. Furthermore, good accuracy of the PorPc-CMP PEC sensor was demonstrated in real sample analysis of H2O2 disinfectant and human serum samples. This journal is
Subphthalocyanines as Efficient Photosensitizers with Nanomolar Photodynamic Activity against Cancer Cells
Demuth, Jiri,Gallego, Lucia,Kozlikova, Magdalena,Kucera, Radim,Machacek, Miloslav,Martinez-Diaz, M. Victoria,Novakova, Veronika,Torres, Tomas
, p. 17436 - 17447 (2021/12/06)
Because cancer is the second leading cause of death globally, investigation of new photosensitizers for photodynamic therapy is highly desirable. In this work, different peripherally substituted subphthalocyanines (SubPcs) with either a benzocrown moiety (CE-) or a tyrosine methyl ester (Tyr-) as the axial ligand have been prepared. Target SubPcs showed high φΔ values, >0.50 in EtOH. Both CE- and Tyr- moieties increased substantially the hydrophilicity of the compounds (log P = 1.79-2.63, n-octanol/PBS). Uptake to cells, subcellular localization, and monitoring of the progression of cell death over time are described. Improved spectroscopic behavior of the CE- series in cell culture medium resulted in higher photodynamic activity versus that of the Tyr- series. In particular, the peripherally triethylsulfanyl SubPc-CE exhibited extraordinarily low EC50 values of 2.3 and 4.4 nM after light activation and high TC50 values of 14.49 and 5.25 μM (i.e., dark toxicity without activation) on SK-MEL-28 and HeLa cells, respectively, which rank it among the best photosensitizers ever.
Palladium(II) phthalocyanines efficiently promote phosphine-free Sonogashira cross-coupling reaction at room temperature
Platonova, Yana B.,Tomilova, Larisa G.,Volov, Alexander N.
, p. 224 - 228 (2020/09/17)
Herein we report that exceptionally simple and inexpensive Pd(II) complexes of phthalocyanines efficiently catalyze direct formation of diphenylacetylenes at ambient conditions with low loading of catalyst (0.5 mol%). Results of this study demonstrate that terminal alkynes reacted mildly with p-substituted aryl bromides at room temperature under Pd and Cu-cocatalysis to give the corresponding phenylacetylenes in yields up to 98%. Also we have examined this catalyst in Sonogashira cross-coupling with aryl chlorides and it was very effective and this reaction at room temperature that there is no examples in recent articles. This protocol represents the first use of palladium phthalocyanine as homogeneous catalyst in the Pd/Cu-promoted Sonogashira reaction. The palladium(II) phthalocyanine complex is significantly more active in Sonogashira cross-coupling between aryl halides and terminal alkynes as compared with traditional catalysts because of absence of palladium black formation through agglomeration of metal particles and deactivation of catalyst.