Polycyclic Arene-Fused Selenophenes via Site Selective Selenocyclization of Arylethynyl Substituted Polycyclic Arenes

Autor:	Nani Gopal Ghosh, Sanjio S. Zade, Abhijeet R. Agrawal, Chandan Kumar, Neha Rani Kumar, Himadri S. Karmakar, Sarasija Das
Rok vydání:	2021
Předmět:	chemistry.chemical_compound chemistry Organic Chemistry Substituent Substrate (chemistry) Pyrene Quantum yield Benzene Medicinal chemistry Redox Catalysis Naphthalene
Zdroj:	The Journal of Organic Chemistry. 86:12494-12506
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.1c00689
Popis:	Arene-fused selenophenes were synthesized by a redox neutral process from arylethynyl substituted polycyclic arenes using selenium powder in refluxing N-methyl-2-pyrrolidone (NMP) with the assistance of the residual water in NMP as a catalytic proton source. The site-selective nature of this selenocyclization produces trans-alkenes as a competitive product, which is dependent on the π-electron donation ability of polycyclic arenes and the kind of arylethynyl group attached to it. DFT calculations were performed to understand the site selectivity in the selenophene formation reaction. The HOMO coefficient on the carbon adjacent to carbon having arylalkyne substituent of the polycyclic arene correlates with the selenocyclization tendency of the substrate. The wavelength of absorption and emission and quantum yield of emission increase with increasing the number of fused benzene rings in the polycyclic unit (from naphthalene to pyrene).
Databáze:	OpenAIRE
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