- The synthesis, photophysical and electrochemical studies of symmetrical phthalocyanines linked thiophene substituents
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Tetrakis 4-(3-thienyl) and tetrakis 4-(5′-hexyl-2,2′- bithiophene) peripherally substituted zinc phthalocyanines were synthesized by using phthalonitrile derivatives. The phthalonitrile compounds were obtained through palladium catalyzed Suzuki-Miyaura cr
- Cogal, Sadik,Ocakoglu, Kasim,Oksuz, Aysegul Uygun
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- Axial and peripheral tetraarylethylene-modified subphthalocyanines with distinctive fluorescent performances
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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.
- Ding, Wei,Yan, Liying,Cao, Fei,Luo, Qianfu
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supporting information
(2021/05/06)
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- A high-performance photoelectrochemical sensor for the specific detection of H2O2and glucose based on an organic conjugated microporous polymer
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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
- Chen, Yanli,Gao, Wen,Kong, Xia,Li, Xiyou,Liu, Qi,Liu, Xue,Shen, Jingshun,Sun, Qiqi,Xing, Chuanwang,Zhang, Yuexing
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supporting information
p. 26216 - 26225
(2021/12/13)
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- Subphthalocyanines as Efficient Photosensitizers with Nanomolar Photodynamic Activity against Cancer Cells
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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.
- Demuth, Jiri,Gallego, Lucia,Kozlikova, Magdalena,Kucera, Radim,Machacek, Miloslav,Martinez-Diaz, M. Victoria,Novakova, Veronika,Torres, Tomas
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p. 17436 - 17447
(2021/12/06)
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- Supramolecular subphthalocyanine complexes-cellular uptake and phototoxicity
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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.
- Dubbert, Justin,H?ing, Alexander,Knauer, Shirley K.,Riek, Nathalie,Voskuhl, Jens
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supporting information
p. 7653 - 7656
(2020/08/25)
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- Cellular imaging using BODIPY-, pyrene- and phthalocyanine-based conjugates
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Fluorescent Probes aimed at absorbing in the blue/green region of the spectrum and emitting in the green/red have been synthesized (as the form of dyads-pentads), studied by spectrofluorimetry, and used for cellular imaging. The synthesis of phthalocyanin
- Bizet, Faustine,Ipuy, Martin,Bernhard, Yann,Lioret, Vivian,Winckler, Pascale,Goze, Christine,Perrier-Cornet, Jean-Marie,Decréau, Richard A.
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p. 413 - 420
(2018/01/05)
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- HOLE TRANSPORT BED MATERIAL AND SOLAR CELL USING HOLE TRANSPORT BED MATERIAL
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PROBLEM TO BE SOLVED: To provide a hole transport bed material having superior hole transportability and durability cheaply, and a solar cell having high photoelectric conversion efficiency by using the hole transport bed material. SOLUTION: A hole transp
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Paragraph 0080
(2017/08/02)
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- Colored Dye for color filter and Preparation method thereof
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The present invention relates to a coloring dye for color filters and a photosensitive resin composition including the same. More specifically, provided are a coloring dye for color filters, which exhibits excellent heat resistance, light resistance, chemical resistance, and high brightness. To this end, a certain ionic substituent capable of increasing solubility such as cyanoacetic acid is added into phthalocyanine, and a strong electron withdrawing group capable of increasing solubility in solvents is substituted. In addition, a light-absorption region is shifted to a blue region. Also, provided is a photosensitive resin composition including the same.
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Paragraph 0151-0155
(2017/02/02)
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- Asymmetric phthalocyanine derivatives containing 4-carboxyphenyl substituents for dye-sensitized solar cells
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The synthesis of two asymmetrical zinc (II) phthalocyanines (ZnPcs) containing 4-carboxyphenyl and 3-thienyl or 5′-hexyl-2,2′-bithiophene substituent was described. These Zinc Phthalocyanines were synthesized by a statistical condensation reaction between two different phthalonitriles. Each of the phthalonitrile precursors was accomplished by the Suzuki-Miyaura cross-coupling reactions with the aryliodide and corresponding boronic acids. The ZnPc dyes were characterized by MALDI-MS, FT-IR, 1H NMR, UV-Vis, fluorescence and cyclic voltammetry methods. Compared with 3-thienyl substituted ZnPc-1 dye, the Q-band absorption of 5′-Hexyl-2,2′-bithiophene substituted ZnPc-2 was red-shifted by 13 nm because of the extension of π-system. The ZnPc dyes were used as sensitizers in dye-sensitized solar cells (DSSCs). ZnPc-2 sensitized solar cell devices using a 7 (transparent) + 5 (scattering) μm thin TiO2 layer yielded a short-circuit photocurrent density of 3.81 mA/cm2, an open-circuit voltage of 500 mV, and a fill factor of 0.59, corresponding to an overall conversion efficiency of 1.12% under standard AM 1.5 sun light.
- Cogal, Sadik,Erten-Ela, Sule,Ocakoglu, Kasim,Oksuz, Aysegul Uygun
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p. 474 - 480
(2015/03/18)
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- Synthesis of phthalonitrile derivatives by photoinduced reactions. New unsymmetrical substituted zinc phthalocyanines
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The synthesis of new phthalonitrile derivatives by photoinduced reaction is described. Novel unsymmetrically substituted Zn(II) phthalocyanine bearing an aryl alcohol group (ArZnPc) was synthesized by the ring expansion reaction of boron(III) subphthalocyanine chloride with an appropriated phthalonitrile. The spectroscopic and photodynamic properties of these ArZnPc were studied.
- Tempesti, Tomas C.,Baumgartner, María T.
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p. 1088 - 1094
(2016/01/15)
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- The synthesis, photophysical and electrochemical studies of symmetrical phthalocyanines linked thiophene substituents
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Tetrakis 4-(3-thienyl) and tetrakis 4-(50-hexyl-2,20-bithiophene) peripherally substituted zinc phthalocyanines were synthesized by using phthalonitrile derivatives. The phthalonitrile compounds were obtained through palladium catalyzed Suzuki-Miyaura cro
- Cogal, Sadik,Ocakoglu, Kasim,Oksuz, Aysegul Uygun
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p. 139 - 144
(2014/12/11)
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- CROSS-LINKABLE COPPER PHTHALOCYANINE COMPLEXES
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Cross-linkable copper complexes comprising a copper phthalocyanine core and one or more cross-linkable functionalities linked to the phthalocyanine core. The copper complex may have a spacer group with the one or more cross-linkable functionalities on the spacer group. The spacer group contains a chain or one or more aryl groups. These cross-linkable copper complexes may be used in making organic electronic devices, such as OLEDs, by solution processing techniques.
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Page/Page column 21
(2012/11/07)
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- Synthesis of a novel unsymmetrical Zn(ii) phthalocyanine bearing a phenyl ethynyl moiety as sensitizer for dye-sensitized solar cells
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A new unsymmetrical zinc phthalocyanine sensitizer has been synthesised. The anchoring of the molecule to nanocrystalline TiO2 films is realised by a carboxylic group connected to a phenyl ethynyl moiety. Density Functional Theory (DFT) calculations show significant and positive effects of such a functionalization. Electron injection into the semiconductor and photocurrent generation in DSSC are also presented.
- Zanotti, Gloria,Angelini, Nicola,Paoletti, Anna Maria,Pennesi, Giovanna,Rossi, Gentilina,Bonapasta, Aldo Amore,Mattioli, Giuseppe,Di Carlo, Aldo,Brown, Thomas M.,Lembo, Angelo,Reale, Andrea
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supporting information; scheme or table
p. 38 - 40
(2011/02/27)
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- An application of the stille coupling for the preparation of arylated phthalonitriles and phthalocyanines
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The substituted phthalonitriles 4-phenylphthalonitrile (2a), 4-(2,5-dimethoxyphenyl)phthalonitrile (2b) and 2-(3,4-dicyanophenyl)-4-methylpyridine (2c) have been prepared in good yields from 4-iodophthalonitrile 3, the synthesis of which is also discussed, using the Stille coupling method. Such phthalonitriles are precursors for phthalocyanines with the possibility of biphenyl-like orientation of a peripheral substituent with respect to the macrocycle ring plane. As an example, 2b was used in the preparation of tetra(dimethoxyphenyl)phthalocyanine 1a. Both 1a and the corresponding zinc(II) complex show good solubility in non-polar solvents such as dichloromethane.
- Aranyos, Viviane,Castano, Ana M.,Grennberg, Helena
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p. 714 - 720
(2007/10/03)
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- Vibrational spectra of halophthalonitriles
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The fundamental vibrational modes of a series of six halophthalonitriles have been studied using Raman and infrared spectroscopy. The vibrational assignment of experimental wave numbers obtained from solid samples was aided using quantum chemical computations. Semi-empirical methods and the local SVWN functional were used to obtain vibrational wave numbers and atomic displacement representations of the fundamental molecular vibrations. The study of a series of molecules with similar structure permits the identification of characteristic wave numbers and the effect of the halosubstitution in the molecular structure.
- Halls, Mathew D.,Aroca, Ricardo,Terekhov, Dmitri S.,D'Ascanio, Anna,Leznoff, Clifford C.
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p. 305 - 317
(2007/10/03)
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- Binuclear phthalocyanines covalently linked through two- and four-atom bridges
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Binuclear phthalocyanines in which the two phthalocyanine nuclei are covalently linked through four-atom bridges, derived from catechol, have been prepared and characterized.Metal-free 2,9,16,23-tetra-(3,3-dimethylbutyl)phthalocyanine and 2,9,16,23-tetra-(2-trimethylsilylethyl)phthalocyanine were prepared as examples of non-oxygenated mononuclear phthalocyanines soluble in organic solvents.Catalytic hydrogenation of 1,2-bis-(3,4-dicyanophenyl)ethyne and 1,4-bis-(3,4-dicyanophenyl)buta-1,3-diyne gave 1,2-bis-(3,4-dicyanophenyl)ethane and 1,4-bis-(3,4-dicyanophenyl)butane respectively.From these precursors, metal-free phthalocyanine dimers containing ethylene and tetramethylene bridges, joining the phthalocyanine nuclei, were prepared.Two of the two-atom bridge phthalocyanine dimers represent the first characterized phthalocyanine dimers not containing alkoxy or oxygenated groups.
- Marcuccio, Sebastian M.,Svirskaya, Polina I.,Greenberg, Shafrira,Lever, A. B. P.,Leznoff, Clifford C.,Tomer, Kenneth B.
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p. 3057 - 3069
(2007/10/02)
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- Preparation of iodophthalonitrile
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Iodophthalonitrile is prepared by mixing aminophthalonitrile with sulfuric acid at a temperature below 25° C., reacting that product with sodium nitrite at a temperature below 15° C., and reacting that product with potassium iodide at a temperature below
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- Fluorinated phthalonitriles
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A fluorinated phthalonitrile of the general formula: STR1 wherein R' is F or CF3, R is (CF2)p, m is 1 or 2, n is 1 or, p is an integer from 3 to 30, x is 1, 2, or 3, y is 1, 2, or 3 and z is 0 or 1 is prepared by reacting
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