Chiral Distorted Hexa-peri-hexabenzocoronenes Bearing a Nonagon-Embedded Carbohelicene.
chirality
helicenes
nanographenes
nonagonal carbocycle
polycyclic aromatic hydrocarbons
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:
27 Sep 2021
27 Sep 2021
Historique:
received:
13
07
2021
pubmed:
31
7
2021
medline:
31
7
2021
entrez:
30
7
2021
Statut:
ppublish
Résumé
A new family of chiral saddle-helix hybrid nanographenes is reported. The first hexa-peri-hexabenzocoronene (HBC) analogues bearing a nine-membered carbocycle are presented. Furthermore, for the first time, π-extended carbo[n]helicenes containing a nine-membered ring as part of the helical moiety have been synthesized. The combination of a [5]helicene moiety and a nonagon ring in a single chiral motif induces a tremendous distortion from planarity into the nanographenic structures compared to other saddle-helix hybrids such as heptagon- and octagon-containing π-extended carbo[5]helicenes. In fact, the interplanar angle of the two terminal rings reaches the largest angle (134.8°) of a carbohelicene reported to date, thus being by far the most twisted helicene yet prepared. Photophysical properties evaluation showed improved absorption dissymmetry factors (|g
Identifiants
pubmed: 34329498
doi: 10.1002/anie.202109310
pmc: PMC8518755
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
22051-22056Subventions
Organisme : h2020 european research council
ID : ERC-STG-677023
Organisme : ministerio de ciencia, innovación y universidades
ID : PGC2018-101181-B-I00
Organisme : schweizerischer nationalfonds zur förderung der wissenschaftlichen forschung
ID : CRSK-2_190365
Informations de copyright
© 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
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