Synthesis, Structures, and Properties of Highly Strained Cyclophenylene-Ethynylenes with Axial and Helical Chirality.
alkynes
axial chirality
biaryls
cyclophenylene-ethynylenes
helical chirality
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
05 Oct 2020
05 Oct 2020
Historique:
received:
14
05
2020
pubmed:
4
7
2020
medline:
4
7
2020
entrez:
4
7
2020
Statut:
ppublish
Résumé
Single and double cyclophenylene-ethynylenes (CPEs) with axial and helical chirality have been synthesized by the Sonogashira cross-coupling of di- and tetraethynyl biphenyls with a U-shaped prearomatic diiodoparaphenylene followed by reductive aromatization. X-ray crystallographic analyses and DFT calculations revealed that the CPEs possess highly twisted bent structures. Bend angles on the edge of the paraphenylene units were close to the value of [5]cycloparaphenylene (CPP)-the smallest CPP to date. The double and single CPEs possessed stable chirality despite flexible biphenyl structures because of the high strain in the diethynyl-paraphenylene moiety. In both the single and double CPEs, orbital interactions along the biphenyl axis were observed by DFT calculations in LUMO and LUMO+2 of the single CPE and LUMO+1 of the double CPE, which likely cause lowering of these orbital energies. Concerning chiroptical properties: boosting of the g
Identifiants
pubmed: 32618087
doi: 10.1002/anie.202006959
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
17951-17957Subventions
Organisme : Japan Society for the Promotion of Science
ID : JP19H00893
Organisme : Japan Society for the Promotion of Science
ID : JP18H04504 and JP20H04661
Informations de copyright
© 2020 Wiley-VCH GmbH.
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