Oxidation of Tetraphenylhexaazaanthracene: Accessing a Scissor Dimer of a 16π Biscyanine

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• 作者：Georgia A. Zissimou ; Christos P. Constantinides ; Maria Manoli ; Galatia K. Pieridou ; Sophia C. Hayes ; Panayiotis A. Koutentis
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：March 4, 2016
• 年：2016
• 卷：18
• 期：5
• 页码：1116-1119
• 全文大小：344K
• ISSN：1523-7052

文摘

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.