Synthesis and characterisation of some 1,4,8,11,15,18,22,25-octa(alkoxymethyl)phthalocyanines: A new series of discotic liquid crystals

Andrew N. Cammidge, Michael J. Cook, Kenneth J. Harrison, Neil B. McKeown

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Abstract

A series of 3, 6-bis(alkoxymethyl)phthalonitriles, prepared via Diels–Alder reactions of 2, 5-bis(alkoxymethyl)furans with fumaronitrile, have been converted into the corresponding phthalocyanines. Zn(II) and Cu(II) derivatives of 1,4,8,11,15,18,22,25-octa(heptyloxymethyl)phthalocyanine were also prepared. Examples of the macrocycles were characterised using 1H NMR spectrometry and optical spectroscopy. Those bearing straight chains aggregate in solutions of chloroform and toluene. The octa(butoxymethyl)phthalocyanine and its longer chain homologues exhibit a discotic liquid crystallinephase. Compounds containing branched sidechains are liquid crystals at room temperature.
Original languageEnglish
Pages (from-to)3053-3058
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number12
DOIs
Publication statusPublished - 1991

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