Tetraphenylhexaazaanthracenes: 16π Weakly Antiaromatic Species with Singlet Ground States
Date
2015Author
Constantinides, Christos P.Zissimou, Georgia A.
Berezin, Andrey A.
Ioannou, Theodosia A.
Manoli, Maria
Tsokkou, Demetra
Theodorou, E.
Hayes, Sophia C.
Koutentis, Panayiotis Andreas
ISSN
1523-7060Source
Organic lettersVolume
17Issue
16Pages
4026-4029Google Scholar check
Metadata
Show full item recordAbstract
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. © 2015 American Chemical Society.