Phthalocyanine-related macrocycles: Cross cyclotetramerisation products from 3,4-dicyanothiophenes, 2,3-dicyanothiophene and 3,6-dialkylphthalonitriles

Cook, Michael J. and Jafari-Fini, Ali (2000) Phthalocyanine-related macrocycles: Cross cyclotetramerisation products from 3,4-dicyanothiophenes, 2,3-dicyanothiophene and 3,6-dialkylphthalonitriles. Tetrahedron, 56 (24). pp. 4085-4094. ISSN 0040-4020

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Abstract

Examples of the novel tribenzo[b,g,l]thiopheno[3,4-q]porphyrazine and tribenzo[b,g,l]thiopheno[2,3-q]porphyrazine ring systems have been obtained by cross cyclotetramerisation reactions of 3,6-dialkylphthalonitriles with 3,4-dicyanothiophenes and 2,3-dicyanothiophene respectively. Dibenzodithiophenol[2,3]porphyrazines and benzotrithiopheno[2,3]porphyrazines have also been recovered. Octaoctyl tribenzo[b,g,l]thiopheno[3,4-q]porphyrazine, in particular, shows a strongly split Q-band absorption in the far red region of the spectrum, one component of which is highly bathochromiclaly shifted relative to the corresponding band in octaoctyl phthalocyanine. The compounds, most of which exhibit columnar liquid crystal behaviour, form even, transparent spin-coated films which exhibit a broad band absorption envelope, in some instances extending from 600 nm to beyond 800 nm. Reaction of 2,3-dicyanothiophene with a 2,5-dialkyl-3,4-dicyanothiophene, the latter in excess, gives a product mixture rich in macrocycles derived predominantly from involvement of the former. (C) 2000 Elsevier Science Ltd. All rights reserved.

Item Type: Article
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: Rachel Smith
Date Deposited: 10 May 2011 14:29
Last Modified: 21 Apr 2020 21:14
URI: https://ueaeprints.uea.ac.uk/id/eprint/30120
DOI: 10.1016/S0040-4020(00)00323-9

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