Synthesis, photophysical and photochemical properties of highly soluble phthalocyanines substituted with four 3,5-dimethylpyrazole-1-methoxy groups

被引:56
作者
Bayrak, Riza [2 ]
Akcay, Hakki Turker [3 ]
Durmus, Mahmut [1 ]
Degirmencioglu, Ismail [2 ]
机构
[1] Gebze Inst Technol, Dept Chem, TR-41400 Gebze, Kocaeli, Turkey
[2] Karadeniz Tech Univ, Fac Sci, Dept Chem, TR-61080 Trabzon, Turkey
[3] Rize Univ, Dept Chem, Fac Arts & Sci, TR-53050 Rize, Turkey
关键词
Phthalocyanine; Pyrazole; Photophysical; Photochemical; Quenching; MICROWAVE-ASSISTED SYNTHESIS; METAL-FREE; STRUCTURAL-CHARACTERIZATION; PYRAZOLE DERIVATIVES; QUANTUM YIELDS; DESIGN; METALLOPHTHALOCYANINES; MOIETIES; SILICON; SINGLET;
D O I
10.1016/j.jorganchem.2011.09.002
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The synthesis and characterization of new peripherally tetra-3,5-dimethylpyrazole-1-methoxy substituted metal-free (4), zinc (5), nickel (6), cobalt (7), copper (8) and lead (9) phthalocyanines are described for the first time in this study. The photophysical (fluorescence quantum yields and fluorescence lifetimes) and photochemical (photodegradation and singlet oxygen quantum yields) properties of metal-free (4), zinc (5) and lead (9) phthalocyanines are studied in dimethylsulfoxide (DMSO). Nickel (6), cobalt (7) and copper (8) phthalocyanines (6-8) did not evaluate for this purpose due to transition metal and paramagnetic behavior of central metals in the phthalocyanine cavity. The fluorescence quenching behavior of metal-free (4), zinc (5) and lead (9) phthalocyanines are also investigated. The fluorescence emissions of these phthalocyanines are effectively quenched by 1,4-benzoquinone in DMSO. (C) 2011 Elsevier B.V. All rights reserved.
引用
收藏
页码:3807 / 3815
页数:9
相关论文
共 52 条
[11]   PICOSECOND LASER PHOTOPHYSICS - GROUP-3A PHTHALOCYANINES [J].
BRANNON, JH ;
MAGDE, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (01) :62-65
[12]   Phthalocyanines and phthalocyanine analogues:: The quest for applicable optical properties [J].
Claessens, CG ;
Blau, WJ ;
Cook, M ;
Hanack, M ;
Nolte, RJM ;
Torres, T ;
Wöhrle, D .
MONATSHEFTE FUR CHEMIE, 2001, 132 (01) :3-11
[13]   EXCITED SINGLET AND TRIPLET-STATE ELECTRON-TRANSFER REACTIONS OF ALUMINUM(III) SULFONATED PHTHALOCYANINE [J].
DARWENT, JR ;
MCCUBBIN, I ;
PHILLIPS, D .
JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS II, 1982, 78 :347-357
[14]   New olefinic centred binuclear clamshell type phthalocyanines: Design, synthesis, structural characterisation, the stability and the change in the electron cloud at olefine-based symmetrical diphthalonitrile fragment by the combined application of UV-Vis electronic structure and theoretical methods [J].
Degirmencioglu, Ismail ;
Bayrak, Riza ;
Er, Mustafa ;
Serbest, Kerim .
POLYHEDRON, 2011, 30 (09) :1628-1636
[15]   Novel phthalocyanines containing substituted salicyclic hydrazone-1,3-thiazole moieties: Microwave-assisted synthesis, spectroscopic characterization, X-ray structure and thermal characterization [J].
Degirmencioglu, Ismail ;
Atalay, Esra ;
Er, Mustafa ;
Koysal, Yavuz ;
Isik, Samil ;
Serbest, Kerim .
DYES AND PIGMENTS, 2010, 84 (01) :69-78
[16]   The microwave-assisted synthesis and structural characterization of novel, dithia-bridged polymeric phthalocyanines containing a substituted thiophenylamine Schiff base [J].
Degirmencioglu, Ismail ;
Bayrak, Riza ;
Er, Mustafa ;
Serbest, Kerim .
DYES AND PIGMENTS, 2009, 83 (01) :51-58
[17]   3RD-ORDER NONLINEAR-OPTICAL PROPERTIES OF SOLUBLE OCTASUBSTITUTED METALLOPHTHALOCYANINES [J].
DIAZGARCIA, MA ;
LEDOUX, I ;
DURO, JA ;
TORRES, T ;
AGULLOLOPEZ, F ;
ZYSS, J .
JOURNAL OF PHYSICAL CHEMISTRY, 1994, 98 (35) :8761-8764
[18]  
Du H, 1998, PHOTOCHEM PHOTOBIOL, V68, P141, DOI 10.1562/0031-8655(1998)068<0141:PACADA>2.3.CO
[19]  
2
[20]   Comparison of photophysicochemical properties of hexaphenoxycyclotriphosphazenyl-substituted metal-free, mono- and bis-lutetium phthalocyanines [J].
Durmus, Mahmut ;
Yesilot, Serkan ;
Cosut, Buenyemin ;
Gurek, Ayse Gul ;
Kilic, Adem ;
Ahsen, Vefa .
SYNTHETIC METALS, 2010, 160 (5-6) :436-444