Beilstein J. Org. Chem.2020,16, 791–797, doi:10.3762/bjoc.16.72
Road, Hong Kong, China 10.3762/bjoc.16.72 Abstract A novel dicyclopenta-fused peropyrene derivative 1 was synthesized via a palladium-catalyzed four-fold alkyne annulation of 1,3,6,8-tetrabromo-2,7-diphenylpyrene (5) with diphenylacetylene. The annulative π-extension reaction toward 1 involved a
exhibits a narrow energy gap (1.78 eV) and a lower LUMO energy level than the parent peropyrene without the fusion of the five-membered rings. In addition, the effects of the peri-fused pentagons on the aromaticity and molecular orbitals of 1 were evaluated by theoretical calculations. This work presents
an efficient method to develop π-extended aromatic hydrocarbons with cyclopenta moieties.
Keywords: alkyne annulation; cyclopenta-fused polycyclic aromatic hydrocarbons; nonplanarity; peropyrene; regioselectivity; Introduction
Significant efforts have been recently devoted to the synthesis of
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Graphical Abstract
Scheme 1:
Chemical structures of dicyclopenta-fused pyrene derivatives i–iii, peropyrene and the dicyclopenta...