Synthesis, characterization, electrochemical and CO2 sensing properties of novel mono and ball-type phthalocyanines with four phenolphthalein units

被引:44
作者
Altun, Selcuk [1 ]
Altindal, Ahmet [2 ]
Oezkaya, A. Riza [1 ]
Bulut, Mustafa [1 ]
Bekaroglu, Oezer [3 ]
机构
[1] Marmara Univ, Dept Chem, TR-34722 Goztepe, Turkey
[2] Marmara Univ, Dept Phys, TR-34722 Goztepe, Turkey
[3] Tech Univ Istanbul, Dept Chem, Maslak, Turkey
关键词
phthalocyanine; ball-type; electrochemistry; CO2; sensing;
D O I
10.1016/j.tetlet.2008.05.065
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The novel mono metallo [Zn(II) 4 and Co(II) 5] and ball-type or cofacial bis-metallo [Zn(II) 6 and Co(II) 71 phthalocyanines have been synthesized from 3, which can be obtained by the reaction of 4-nitrophthalonitrile 1 with 3,3-bis(4-hydroxy-phenyl)isobenzofuran-1(3H)-one 2 (phenolphthalein). The phthalocyanines have been characterized by elemental analysis, UV-vis, IR,H-1 NMR, and mass spectroscopy. The redox behavior of the complexes was investigated by cyclic voltammetry and controlled-potential coulometry. The electrochemical measurements suggested the formation of mixed-valent species during the redox processes of bis-metallophthalocyanines 6 and 7, as a result of the intramolecular interactions between two cofacial Pc units. The effect of temperature on the CO2 sensing properties of a spin-coated thin film of 7 was also investigated. (c) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4483 / 4486
页数:4
相关论文
共 19 条
[1]   Synthesis, characterization, and electrochemical and electrochromic properties of sandwich dilutetium tetraphthalocyanine [J].
Abdurrahmanoglu, S ;
Özkaya, AR ;
Bulut, M ;
Bekaroglu, Ö .
DALTON TRANSACTIONS, 2004, (23) :4022-4029
[2]   Synthesis, characterization, and electrical and electrochemical properties of sandwich dilutetium tetraphthalocyanine [J].
Abdurrahmanoglu, S ;
Altindal, A ;
Özkaya, AR ;
Bulut, M ;
Bekaroglu, Ö .
CHEMICAL COMMUNICATIONS, 2004, (18) :2096-2097
[3]  
ATLINDAL A, 2005, SYNTHETIC MET, V150, P181
[4]   Synthesis, characterization and electrochemical properties of novel metal free and zinc(II) phthalocyanines of ball and clamshell types [J].
Ceyhan, T. ;
Altindal, A. ;
Ozkaya, A. R. ;
Celikbicak, O. ;
Salih, B. ;
Erbil, M. Kemal ;
Bekaroglu, O. .
POLYHEDRON, 2007, 26 (15) :4239-4249
[5]   Synthesis, characterization and EPR spectroscopy of novel s-triazines bearing three oxygen-linked phthalocyanines [J].
Ceyhan, T ;
Korkmaz, M ;
Kutluay, R ;
Bekaroglu, Ö .
JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 2004, 8 (12) :1383-1389
[6]   Synthesis, characterization and nonlinear absorption of novel octakis-POSS substituted metallophthalocyanines and strong optical limiting property of CuPc [J].
Ceyhan, Tanju ;
Yueksek, Mustafa ;
Yaghoglu, H. Guel ;
Salih, Bekir ;
Erbil, Mehmet K. ;
Elmali, Ayhan ;
Bekaroglu, Oezer .
DALTON TRANSACTIONS, 2008, (18) :2407-2413
[7]   CONDUCTING STACKED METALLOPHTHALOCYANINES AND RELATED-COMPOUNDS [J].
HANACK, M ;
LANG, M .
ADVANCED MATERIALS, 1994, 6 (11) :819-833
[8]   Patterned growth and contact transfer of well-aligned carbon nanotube films [J].
Huang, SM ;
Dai, LM ;
Mau, AWH .
JOURNAL OF PHYSICAL CHEMISTRY B, 1999, 103 (21) :4223-4227
[9]   Molecular structure and vibrational spectra of phenolphthalein and its dianion [J].
Kunimoto, KK ;
Sugiura, H ;
Kato, T ;
Senda, H ;
Kuwae, A ;
Hanai, K .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2001, 57 (02) :265-271
[10]  
Leznoff C.C., 1989, PHTHALOCYANINES PROP, V1