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Preparation and optical and electrochemical properties of octaethylphthalocyanines fused with several tetrathiafulvalene units

Preparation and optical and electrochemical properties of octaethylphthalocyanines fused with... 3,6‐Diethylphthalonitrile (3) with a tetrathiafulvalene (TTF) unit at 4,5‐positions was prepared from 4,5‐xylylenedithio‐3,6‐diethylphthalonitrile (1a) via elimination of the xylylene group, connection of a carbonyl group to benzenedithiolate generated, and condensation of 4,5‐bis(methylthio)‐1,3‐dithiole‐2‐thione with benzo‐1,3‐dithiole‐2‐one (2‐O) produced. A 1:1 mixture of phthalonitrile (3) and 4,5‐bis(benzylthio)‐3,6‐diethylphthalonitrile (1b) was treated with lithium in n‐hexanol at 120°C to produce hexakis (benzylthio)mono(tetrathiafulvaleno)phthalocyanine (5), tetrakis(benzylthio)bis(tetrathiafulvaleno)phthalocyanine (6), and bis(benzylthio)tris(tetrathiafulvaleno)phthalocyanine (7). The structures of 5, 6, and 7 were determined by 1H NMR, FAB MS, MALDI‐TOF MS (matrix assisted laser desorption ionization time‐of‐flight mass spectrometry), and UV‐‐vis spectroscopy. Compound 6 is a mixture of trans and cis isomers (6‐trans and 6‐cis). The UV‐‐vis spectrum of 5 measured in chloroform changed by addition of trifluoroacetic acid (TFA). The Q band absorption at λmax = 755 nm (chloroform) decreased in intensity and resulted in a new absorption at λmax = 740 nm (chloroform/TFA). The electrochemical properties of 5, 6, and 7 were determined by cyclic voltammetry using Ag/AgNO3 as a reference electrode. © 2011 Wiley Periodicals, Inc. Heteroatom Chem 22:605–611, 2011; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20694 http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Heteroatom Chemistry Wiley

Preparation and optical and electrochemical properties of octaethylphthalocyanines fused with several tetrathiafulvalene units

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Publisher
Wiley
Copyright
Copyright © 2011 Wiley Periodicals, Inc.
ISSN
1042-7163
eISSN
1098-1071
DOI
10.1002/hc.20694
Publisher site
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Abstract

3,6‐Diethylphthalonitrile (3) with a tetrathiafulvalene (TTF) unit at 4,5‐positions was prepared from 4,5‐xylylenedithio‐3,6‐diethylphthalonitrile (1a) via elimination of the xylylene group, connection of a carbonyl group to benzenedithiolate generated, and condensation of 4,5‐bis(methylthio)‐1,3‐dithiole‐2‐thione with benzo‐1,3‐dithiole‐2‐one (2‐O) produced. A 1:1 mixture of phthalonitrile (3) and 4,5‐bis(benzylthio)‐3,6‐diethylphthalonitrile (1b) was treated with lithium in n‐hexanol at 120°C to produce hexakis (benzylthio)mono(tetrathiafulvaleno)phthalocyanine (5), tetrakis(benzylthio)bis(tetrathiafulvaleno)phthalocyanine (6), and bis(benzylthio)tris(tetrathiafulvaleno)phthalocyanine (7). The structures of 5, 6, and 7 were determined by 1H NMR, FAB MS, MALDI‐TOF MS (matrix assisted laser desorption ionization time‐of‐flight mass spectrometry), and UV‐‐vis spectroscopy. Compound 6 is a mixture of trans and cis isomers (6‐trans and 6‐cis). The UV‐‐vis spectrum of 5 measured in chloroform changed by addition of trifluoroacetic acid (TFA). The Q band absorption at λmax = 755 nm (chloroform) decreased in intensity and resulted in a new absorption at λmax = 740 nm (chloroform/TFA). The electrochemical properties of 5, 6, and 7 were determined by cyclic voltammetry using Ag/AgNO3 as a reference electrode. © 2011 Wiley Periodicals, Inc. Heteroatom Chem 22:605–611, 2011; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20694

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Heteroatom Chemistry – Wiley

Published: Sep 1, 2011

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