Pyrenes, Peropyrenes, and Teropyrenes: Synthesis, Structures, and Photophysical Properties
Monteiro, Jorge H. S. K.
de Bettencourt-Dias, Ana
Catalano, Vincent J.
Chalifoux, Wesley A.
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The design of a relatively simple and efficient method to extend the ?-conjugation of readily available aroms. in one-dimension is of significant value. In this paper, pyrenes, peropyrenes, and teropyrenes were synthesized through a double or quadruple benzannulation reaction of alkynes promoted by Bronsted acid. This novel method does not involve cyclodehydrogenation (oxidative aryl-aryl coupling) to arrive at the newly incorporated large arene moieties. All of the target compds. were synthesized in moderate to good yields and were fully characterized with the structures unambiguously confirmed by X-ray crystallog. As expected, photophys. characterization clearly shows increasing red-shifts as a function of extended conjugation within the fused ring systems. [on SciFinder(R)]