Oxidation of Tetraphenylhexaazaanthracene: Accessing a Scissor Dimer of a 16π Biscyanine
Date
2016Author
Zissimou, Georgia A.Constantinides, Christos P.
Manoli, Maria
Pieridou, Galatia K.
Hayes, Sophia C.
Koutentis, Panayiotis Andreas
ISSN
1523-7060Source
Organic lettersVolume
18Issue
5Pages
1116-1119Google Scholar check
Metadata
Show full item recordAbstract
Tetraphenylhexaazaanthracene (TPHA), a fluorescent zwitterionic biscyanine with a closed-shell singlet ground state, on treatment with manganese dioxide or phenyliodine bis(trifluoroacetate) (PIFA), undergoes oxidative dimerization to give a near-zero dipole scissor 5,5′-dimer DI-TPHA. Both acene components of the new dimer DI-TPHA maintain their biscyanine closed-shell singlet ground state motifs, as judged by analysis of both single crystal X-ray crystallographic and density functional theory computational studies however, unlike TPHA, DI-TPHA is only very weakly fluorescent. © 2016 American Chemical Society.