Columnar Mesomorphism of Fluorescent Board-Shaped Quinoxalinophenanthrophenazine Derivatives with Donor–Acceptor Structure

Abstract

Quinoxalino[2′,3′:9,10]phenanthro[4,5-<i>abc</i>]phenazine (QPP) dyes have been studied as electron acceptor materials, fluorophores, and building blocks for self-organizing organic semiconductors. Condensation of tetraketopyrene with electron-rich diamino-terphenylene and -triphenylene derivatives generates new donor–acceptor QPP derivatives that display columnar mesomorphism over wide ranges of temperature; are fluorescent in solution, liquid crystal, and solid phases; and have electron acceptor properties. Also reported are the synthesis and properties of the first diamino-(tetraalkoxy)triphenylene as a valuable new synthon