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Article: One-pot synthesis of dicyclopenta-fused peropyrene via a fourfold alkyne annulation
Title | One-pot synthesis of dicyclopenta-fused peropyrene via a fourfold alkyne annulation |
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Authors | |
Keywords | alkyne annulation cyclopenta-fused polycyclic aromatic hydrocarbons nonplanarity peropyrene regioselectivity |
Issue Date | 2020 |
Publisher | Beilstein-Institut. The Journal's web site is located at http://www.beilstein-journals.org/bjoc/home/home.htm |
Citation | Beilstein Journal of Organic Chemistry, 2020, v. 16, p. 791-797 How to Cite? |
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. |
Persistent Identifier | http://hdl.handle.net/10722/284788 |
ISSN | 2023 Impact Factor: 2.2 2023 SCImago Journal Rankings: 0.517 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Ma, J | - |
dc.contributor.author | Fu, Y | - |
dc.contributor.author | Liu, J | - |
dc.contributor.author | Feng, X | - |
dc.date.accessioned | 2020-08-07T09:02:38Z | - |
dc.date.available | 2020-08-07T09:02:38Z | - |
dc.date.issued | 2020 | - |
dc.identifier.citation | Beilstein Journal of Organic Chemistry, 2020, v. 16, p. 791-797 | - |
dc.identifier.issn | 1860-5397 | - |
dc.identifier.uri | http://hdl.handle.net/10722/284788 | - |
dc.description.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. | - |
dc.language | eng | - |
dc.publisher | Beilstein-Institut. The Journal's web site is located at http://www.beilstein-journals.org/bjoc/home/home.htm | - |
dc.relation.ispartof | Beilstein Journal of Organic Chemistry | - |
dc.rights | This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License. | - |
dc.subject | alkyne annulation | - |
dc.subject | cyclopenta-fused polycyclic aromatic hydrocarbons | - |
dc.subject | nonplanarity | - |
dc.subject | peropyrene | - |
dc.subject | regioselectivity | - |
dc.title | One-pot synthesis of dicyclopenta-fused peropyrene via a fourfold alkyne annulation | - |
dc.type | Article | - |
dc.identifier.email | Liu, J: juliu@hku.hk | - |
dc.identifier.authority | Liu, J=rp02584 | - |
dc.description.nature | published_or_final_version | - |
dc.identifier.doi | 10.3762/bjoc.16.72 | - |
dc.identifier.scopus | eid_2-s2.0-85084402941 | - |
dc.identifier.hkuros | 311676 | - |
dc.identifier.volume | 16 | - |
dc.identifier.spage | 791 | - |
dc.identifier.epage | 797 | - |
dc.identifier.isi | WOS:000526812500001 | - |
dc.publisher.place | Germany | - |
dc.identifier.issnl | 1860-5397 | - |