Water-soluble axially disubstituted non-aggregated silicon phthalocyanines and their electrochemical properties

被引：41

作者：

Biyiklioglu, Zekeriya ^{[1
]}

机构：

[1] Karadeniz Tech Univ, Dept Chem, Fac Sci, TR-61080 Trabzon, Turkey

来源：

DYES AND PIGMENTS | 2013年 / 99卷 / 01期

关键词：

Phthalocyanine; Silicon; Synthesis; Aggregation; Quaternization; Electrochemistry; SITU ELECTROCOLORIMETRIC CHARACTERIZATION; ORGANOSOLUBLE METAL-FREE; SPECTROSCOPIC CHARACTERIZATION; SPECTROELECTROCHEMICAL CHARACTERIZATION; MICROWAVE IRRADIATION; METALLOPHTHALOCYANINES; CO(II); BULKY;

D O I：

10.1016/j.dyepig.2013.04.017

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A series of two novel silicon phthalocyanines 3, 5 and their water-soluble derivatives 3a, 5a have been synthesized by introducing 2-{2-[3-(dimethylamino)phenoxy]ethoxy}ethanol and 2-{2-[3-(diethylamino)phenoxy]ethoxy}ethanol at the axial positions of silicon(IV) phthalocyanine, respectively. The aggregation behaviour of these compounds was investigated in different solvents and concentrations of DMSO and water. Silicon phthalocyanine complexes 3 and 5 and their water-soluble derivatives 3a and 5a did not show any aggregation in CHCl3, CHCl3, DMF, DMSO, THF, EtOH, EtOAc and water. The electrochemistry of complexes 3, 5 was also studied by cyclic voltammetry (CV) and square wave voltammetry (SWV) methods. Complexes 3 and 5 exhibit two reversible Pc ring-based one-electron reduction couples and two quasi-reversible Pc ring-based one-electron oxidation couples. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：59 / 66

页数：8

共 45 条

[1] Novel peripherally tetra-substituted octacationic metal-free and metallophthalocyanines: Synthesis, spectroscopic characterization and aggregation behaviours [J].

Acar, Irfan ;

Cakir, Volkan ;

Biyiklioglu, Zekeriya ;

Kantekin, Halit .

SYNTHETIC METALS, 2012, 162 (17-18) :1546-1557

[2] Synthesis, electrochemical, in situ spectroelectrochemical and in situ electrocolorimetric characterization of new metal-free and metallophthalocyanines substituted with 4-{2-[2-(1-naphthyloxy)ethoxy]ethoxy} groups [J].

Acar, Irfan ;

Biyiklioglu, Zekeriya ;

Koca, Atif ;

Kantekin, Halit .

POLYHEDRON, 2010, 29 (05) :1475-1484

[3] Electrochemical and spectroelectrochemical characterization of newly synthesized manganese, cobalt, iron and copper phthalocyanines [J].

Arici, Mursel ;

Arican, Duygu ;

Ugur, Ahmet Lutfi ;

Erdogmus, Ali ;

Koca, Atif .

ELECTROCHIMICA ACTA, 2013, 87 :554-566

[4] Synthesis and characterization of novel metal-free phthalocyanines substituted with four diazadithiatetraoxa or diazahexaoxamacrobicyclic moieties [J].

Bilgin, A ;

Gök, Y .

TETRAHEDRON LETTERS, 2002, 43 (30) :5343-5347

[5] Synthesis, characterization and electrochemistry of a new organosoluble metal-free and metallophthalocyanines [J].

Biyikhoglu, Zekeriya ;

Guner, Ece Tugba ;

Topcu, Saim ;

Kantekin, Halit .

POLYHEDRON, 2008, 27 (06) :1707-1713

[6] A novel metal-free and metallophthalocyanines containing four 19-membered dithiadiazadioxa macrocycles by microwave irradiation: Synthesis and characterization [J].

Biyikhoglu, Zekeriya ;

Kantekin, Halit .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2008, 693 (03) :505-509

[7] The synthesis, using microwave irradiation and characterization of novel, organosoluble metal-free and metallophthalocyanines substituted with flexible crown ether moieties [J].

Biyiklioglu, Zekeriya ;

Kantekin, Halit .

DYES AND PIGMENTS, 2009, 80 (01) :17-21

[8] Synthesis and spectroscopic characterisation of non-aggregated novel axially 4-{2-[3-(diethylamino)phenoxy]ethoxy} and crown ether substituted silicon phthalocyanines [J].

Biyiklioglu, Zekeriya .

COLORATION TECHNOLOGY, 2012, 128 (06) :459-463

[9] Novel axially disubstituted non-aggregated silicon phthalocyanines [J].

Biyiklioglu, Zekeriya ;

Cakir, Dilek .

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2012, 98 :178-182

[10] Peripheral and non-peripheral long-chain tetrasubstituted phthalocyanines: Synthesis, spectroscopic characterization and aggregation properties [J].

Biyiklioglu, Zekeriya ;

Acar, Irfan .

SYNTHETIC METALS, 2012, 162 (13-14) :1156-1163

← 1 2 3 4 5 →