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Tetraphenylhexaazaanthracenes: 16π weakly antiaromatic species with singlet ground states

Constantinides, Christos P., Zissimou, Georgia A., Berezin, Andrey A., Ioannou, Theodosia A., Manoli, Maria, Tsokkou, Demetra, Theodorou, Eleni, Hayes, Sophia C. and Koutentis, Panayiotis A. 2015. Tetraphenylhexaazaanthracenes: 16π weakly antiaromatic species with singlet ground states. Organic Letters 17 (16) , pp. 4026-4029. 10.1021/acs.orglett.5b01923

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Abstract

Tetraphenylhexaazaanthracene, TPHA-1, is a fluorescent zwitterionic biscyanine with a closed-shell singlet ground state. TPHA-1 overcomes its weak 16π antiaromaticity by partitioning its π system into 6π positive and 10π negative cyanines. The synthesis of TPHA-1 is low yielding and accompanied by two analogous TPHA isomers: the deep red, non-charge-separated, quinoidal TPHA-2, and the deep green TPHA-3 that partitions into two equal but oppositely charged 8π cyanines. The three TPHA isomers are compared.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: American Chemical Society
ISSN: 1523-7060
Last Modified: 24 Jan 2020 13:15
URI: http://orca-mwe.cf.ac.uk/id/eprint/128748

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