Phthalocyaninodehydroannulenes

Cook, Michael J. and Heeney, Martin J. (2000) Phthalocyaninodehydroannulenes. Chemistry - A European Journal, 6 (21). pp. 3958-3967. ISSN 0947-6539

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Abstract

4-Bromo- and 4,5-dibromo-3,6-dibutoxyphthalonitrile have been prepared and treated with 3,6-didecylphthalonitrile in cross tetramerisation reactions in the presence of nickel acetate to afford monobromo- and dibromo-dibutoxyhexadecylphthalocyaninato nickel(II) complexes. Sonogashira and Stille coupling reactions on these compounds displaced the bromine substituents by ethynyl groups. Oxidative coupling of the monoethynyl derivatised nickel phthalocyanine afforded a butadiynyl-linked dinuclear phthalocyanine. The corresponding coupling reaction of the diethynylated phthalocyanine gave a mixture of phthalocyaninodehydroannulenes. Separation of the mixture yielded the diphthalocyaninodehydro[12]annulene as the major product. Electrospray mass spectrometry provides evidence for its aggregation in solution. The corresponding cyclic trimer, the triphthalocyaninodehydro[18]annulene. has been identified as a minor product. Both compounds show a large splitting of the Q-band absorption in the visible region spectrum, Most of the mononuclear phthalocyanine precursors exhibit discotic liquid crystal behaviour. The diphthalocyaninodehydro[12]annulene also enters a mobile phase on heating, hut undergoes an irreversible change at 220 degreesC. MALDI-TOF mass spectrometry of the product reveals that the compound undergoes oligomerisation at this temperature.

Item Type:	Article
Faculty \ School:	Faculty of Science > School of Chemistry (former - to 2024)
Depositing User:	Rachel Smith
Date Deposited:	10 May 2011 15:14
Last Modified:	24 Sep 2024 10:26
URI:	https://ueaeprints.uea.ac.uk/id/eprint/30119
DOI:	10.1002/1521-3765(20001103)6:21<3958::AID-CHEM3958>3.0.CO;2-Y

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