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Article: Thiophene fused indenocorannulenes: Synthesis, variable emission, and exceptional chiral configurational stability

TitleThiophene fused indenocorannulenes: Synthesis, variable emission, and exceptional chiral configurational stability
Authors
Tian, XiaoqiChaiworn, SuchayaXu, JunVanthuyne, NicolasBaldridge, Kim K.Siegel, Jay S.
Issue Date2021
Citation
Organic Chemistry Frontiers, 2021, v. 8, n. 14, p. 3653-3658 How to Cite?
DOI: http://dx.doi.org/10.1039/d1qo00596k
AbstractA set of thiophene fused indenocorannulenes (TFICs) was synthesized and characterized by X-ray crystallography, electrochemical, and photophysical methods. Two chiral derivatives were resolved and their absolute configurations defined by Flack analysis (12a) and by comparison of experimental VCD/ECD spectra with hybrid DFT methods (12b and 3a). The emission wavelengths of 13 compounds were compared and varied over 220 nm (emission colors from violet to red). The bowl-inversion activation barrier of 12 was determined to be 192.7 kJ mol-1, corresponding to a configurational stability of weeks at 200 °C; on par with the highest helicene and phosphine values.
Persistent Identifierhttp://hdl.handle.net/10722/341320
ISSN
2052-4110
2020 SCImago Journal Rankings: 1.377
ISI Accession Number ID
WOS:000661972600001

 

DC FieldValueLanguage
dc.contributor.authorTian, Xiaoqi-
dc.contributor.authorChaiworn, Suchaya-
dc.contributor.authorXu, Jun-
dc.contributor.authorVanthuyne, Nicolas-
dc.contributor.authorBaldridge, Kim K.-
dc.contributor.authorSiegel, Jay S.-
dc.date.accessioned2024-03-13T08:41:53Z-
dc.date.available2024-03-13T08:41:53Z-
dc.date.issued2021-
dc.identifier.citationOrganic Chemistry Frontiers, 2021, v. 8, n. 14, p. 3653-3658-
dc.identifier.issn2052-4110-
dc.identifier.urihttp://hdl.handle.net/10722/341320-
dc.description.abstractA set of thiophene fused indenocorannulenes (TFICs) was synthesized and characterized by X-ray crystallography, electrochemical, and photophysical methods. Two chiral derivatives were resolved and their absolute configurations defined by Flack analysis (12a) and by comparison of experimental VCD/ECD spectra with hybrid DFT methods (12b and 3a). The emission wavelengths of 13 compounds were compared and varied over 220 nm (emission colors from violet to red). The bowl-inversion activation barrier of 12 was determined to be 192.7 kJ mol-1, corresponding to a configurational stability of weeks at 200 °C; on par with the highest helicene and phosphine values.-
dc.languageeng-
dc.relation.ispartofOrganic Chemistry Frontiers-
dc.titleThiophene fused indenocorannulenes: Synthesis, variable emission, and exceptional chiral configurational stability-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1039/d1qo00596k-
dc.identifier.scopuseid_2-s2.0-85110382348-
dc.identifier.volume8-
dc.identifier.issue14-
dc.identifier.spage3653-
dc.identifier.epage3658-
dc.identifier.eissn2052-4129-
dc.identifier.isiWOS:000661972600001-

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