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Coplanarity in the Backbones of Ladder-type Oligo(p-phenylene) Homologues and Derivatives

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posted on 26.10.2006, 00:00 by Ken-Tsung Wong, Liang-Chen Chi, Shih-Chiang Huang, Yuan-Li Liao, Yi-Hung Liu, Yu Wang
p-Tolyl-substituted ladder-type oligo(p-phenylene)s containing three, four, and five phenylene rings were readily synthesized. The uniform aryl substitution of these systems allowed us to determine the coplanarity of the π-conjugated backbones crystallographically. The intramolecular annulations eliminate almost all of the conformational disorder and enhance the degree of π-conjugation of the backbones, resulting in significant red shifts in the absorption and emission maxima and lower oxidation potentials in the higher homologues.