title: Pyrenes, Peropyrenes, and Teropyrenes: Synthesis, Structures, and Photophysical Properties.
abstract: The design of a relatively simple and efficient method to extend the π-conjugation of readily available aromatics 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 Brønsted 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 compounds were synthesized in moderate to good yields and were fully characterized with the structures unambiguously confirmed by X-ray crystallography. As expected, photophysical characterization clearly shows increasing red-shifts as a function of extended conjugation within the fused ring systems.
authors.affiliation: Department of Chemistry, University of Nevada, Reno, 1664 N. Virginia St., Reno, NV, 89557, USA.
authors.forename: Wenlong
authors.initials: W
authors.lastname: Yang
authors.affiliation: Department of Chemistry, University of Nevada, Reno, 1664 N. Virginia St., Reno, NV, 89557, USA.
authors.forename: Jorge H S K
authors.initials: JH
authors.lastname: Monteiro
authors.affiliation: Department of Chemistry, University of Nevada, Reno, 1664 N. Virginia St., Reno, NV, 89557, USA.
authors.forename: Ana
authors.initials: A
authors.lastname: de Bettencourt-Dias
authors.affiliation: Department of Chemistry, University of Nevada, Reno, 1664 N. Virginia St., Reno, NV, 89557, USA.
authors.forename: Vincent J
authors.initials: VJ
authors.lastname: Catalano
authors.affiliation: Department of Chemistry, University of Nevada, Reno, 1664 N. Virginia St., Reno, NV, 89557, USA. wchalifoux@unr.edu.
authors.forename: Wesley A
authors.identifier: 0000-0002-6849-6829
authors.initials: WA
authors.lastname: Chalifoux
keywords: Brønsted acid; alkynes; annulations; arenes; macrocycles