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Azoporphyrin : the porphyrin analogue of azobenzene

By Louisa J. Esdaile, Paul Jensen, John C. McMurtrie and Dennis P. Arnold

Abstract

Azobenzenes (1,2-diaryldiazenes) are very important organic\ud pigments, and they have a unique place in the field of\ud photoresponsive conjugated molecules due to their (usually)\ud reversible E/Z photoisomerisation. The current intense interest in\ud molecular analogues of mechanical components and information\ud storage and processing elements has stimulated research into\ud conjugated molecules whose shape and/or optical properties can be\ud switched electro- or photochemically. Among the classes of\ud conjugated pigments being explored in these contexts are the\ud porphyrinoids, which offer advantages of intense light absorption, a\ud variety of accessible oxidation states, and synthetic control of\ud properties through peripheral or central substitution. Extension of\ud porphyrinoid conjugation can be achieved by linking the peripheral\ud carbons either by three direct bonds (as in the “porphyrin tapes” of\ud Osuka et al.) or through potentially conjugating bridges such as\ud alkenes or, even better, alkynes

Topics: 030503 Organic Chemical Synthesis, porphyrinoids, azo compounds, crystal structure, copper-catalysed coupling, absorption spectroscopy
Publisher: John Wiley & Sons
Year: 2007
DOI identifier: 10.1002/anie.200604658
OAI identifier: oai:eprints.qut.edu.au:40625

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