π-Extension of the Tribenzotriquinacene Framework: Efficient Vinylene and Arylene Bay Bridging Based on a New C3 -Symmetric Key Derivative.

Abstract

1,5,9-Tribromo-2,3,6,7,10,11-hexamethoxy-4b1 -methyltribenzotriquinacene, a C3 -symmetric TBTQ derivative, can be prepared conveniently and with high regioselectivity from readily available starting materials. It is a versatile key compound for the synthesis of other chiral 1,5,9-trifunctionalized TBTQ derivatives and π-extended congeners in which the bays of the TBTQ skeleton are bridged by vinylene and 1,2-arylene units. X-ray crystal structure analysis and UV-vis spectroscopy show that vinylene bay-bridging enables better π-conjugation with the arene rings of the TBTQ core than 1,2-arylene bay-bridging does.