Expanded Porphyrin-like Structures Based on Twinned Triphenylenes

• DOI: 10.1021/jo401551c
• Publication Date: 2013-08-29T13:15:53Z
• Authors: Hemant Gopee; Xiangfei Kong; Zhiqun He; Isabelle Chambrier; David L. Hughes; Graham J. Tizzard; Simon J. Coles; Andrew N. Cammidge
• Keywords: Models, Molecular; Molecular Structure; 540; 01 natural sciences; Chrysenes; 620; 0104 chemical sciences

Triphenylene twins are intriguing structures, and those bridged through their 3,6-positions by dipyrromethene units give a new class of macrocycles that can be viewed as rigid, expanded porphyrin derivatives in which coplanarity is enforced in a formally antiaromatic π system. Somewhat surprisingly, however, macrocyclization leads to significant overall stabilization of the dipyrromethene chromophores.