A Family of Superhelicenes: Easily Tunable, Chiral Nanographenes by Merging Helicity with Planar π Systems.
circular dichroism
helicenes
luminescence
nanographene
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:
09 Aug 2021
09 Aug 2021
Historique:
revised:
22
04
2021
received:
05
03
2021
pubmed:
21
5
2021
medline:
21
5
2021
entrez:
20
5
2021
Statut:
ppublish
Résumé
We designed a straightforward synthetic route towards a full-fledged family of π-extended helicenes: superhelicenes. They have two hexa-peri-hexabenzocoronenes (HBCs) in common that are connected via a central five-membered ring. By means of structurally altering this 5-membered ring, we realized a versatile library of molecular building blocks. Not only the superhelicene structure, but also their features are tuned with ease. In-depth physico-chemical characterizations served as a proof of concept thereof. The superhelicene enantiomers were separated, their circular dichroism was measured in preliminary studies and concluded with an enantiomeric assignment. Our work was rounded-off by crystal structure analyses. Mixed stacks of M- and P-isomers led to twisted molecular wires. Using such stacks, charge-carrier mobilities were calculated, giving reason to expect outstanding hole transporting properties.
Identifiants
pubmed: 34014601
doi: 10.1002/anie.202103253
pmc: PMC8456895
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
18073-18081Subventions
Organisme : Deutsche Forschungsgemeinschaft
ID : 182849149
Organisme : Graduate School of Molecular Science, Friedrich-Alexander-Universität Erlangen-Nürnberg
Informations de copyright
© 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
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