Diindole[3, 2-b:4, 5-b′]pyrrole as a chromophore containing three successively fused pyrroles: synthesis, optoelectronic properties and π-functionalization. Issue 7 (18th February 2016)

• Record Type: Journal Article
• Authors: Jiang, Ming-Jian; Xiao, Wen-Jing; Huang, Jin-Chang; Li, Wei-Shi; Mo, Yue-Qi
• Is Part Of: Tetrahedron. Volume 72:Issue 7(2016)
• Page Start: 979
• Page End: 984
• Publication Date: 2016-02-18
• Subjects: Diindole[3, 2-b:4, 5-b′]pyrrole -- Cadogan reductive cyclization -- Aryl-aryl cross coupling -- Fused-ring aromatic compounds -- Dipyrrolopyrole; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.12.069
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Diindole[3, 2- b :4, 5- b ′]pyrrole (DIP ) is an interesting chromophore containing three successively fused pyrrole rings. However, its basic properties and further π-functionalization have been rarely explored. In this article, two DIP compounds with alkyl or aromatic substituents at the central N position were successfully prepared. The preliminary optoelectronic properties of them also were studied. The property of possessing two reversible oxidation redox couples also agrees with their electron-rich nature. Similar to the alkyl case, the aromatic substitution at the central N position has subtle influence onDIP basic optoelectronic properties. Furthermore, these two compounds can be easily π-modified via the attachment of various π moieties at 2, 9 or 3, 8 positions ofDIP skeleton. Compared with that at 2, 9 positions, π-functionalization at 3, 8 positions showed a much better π-extension effect. Graphical abstract: