Synthesis, fluorescence properties, and head-to-tail regioselectivity in the photodimerization of a donor-acceptor-substituted anthracene

The novel 2,6-donor-acceptor-substituted anthracene, namely 6-methoxy-2-ant hracene carboxylic acid (7), was synthesized. The emission of this compound exhibits significant solvatochromism. The fluorescence band position and i ntensity are also remarkably sensitive to H+. Irradiation of the anthracene 7 in solution yields the syn and anti head-to-tail dimers exclusively. A s ynergistic electronic effect between the donor and acceptor substituents is proposed to operate on the photophysical and photochemical properties of a nthracene 7.