One-pot synthesis of dicyclopenta-fused peropyrene via a fourfold alkyne annulation
Ma J, Fu Y, Liu J, Feng X (2020)
Publication Type: Journal article
Publication year: 2020
Journal
Book Volume: 16
Pages Range: 791-797
DOI: 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 twofold [3 + 2] cyclopentannulation and subsequent twofold [4 + 2] benzannulation. The structure of 1 is unambiguously confirmed by X-ray crystallography; 1 adopted a twisted geometry due to the steric hindrance of the phenyl rings and the hydrogen substituents at the bay regions. Notably, compound 1 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.
Involved external institutions
Hong Kong (HK)
Germany (DE)How to cite
APA:
Ma, J., Fu, Y., Liu, J., & Feng, X. (2020). One-pot synthesis of dicyclopenta-fused peropyrene via a fourfold alkyne annulation. Beilstein Journal of Organic Chemistry, 16, 791-797. https://doi.org/10.3762/bjoc.16.72
MLA:
Ma, Ji, et al. "One-pot synthesis of dicyclopenta-fused peropyrene via a fourfold alkyne annulation." Beilstein Journal of Organic Chemistry 16 (2020): 791-797.
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