S-shaped para-Quinodimethane-Embedded Double [6]Helicene and Its Charged Species Showing Open-Shell Diradical Character.
diradicaloid
helicenes
isomerization
polycycles
quinodimethanes
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
01 Dec 2020
01 Dec 2020
Historique:
received:
19
06
2020
pubmed:
3
7
2020
medline:
3
7
2020
entrez:
3
7
2020
Statut:
ppublish
Résumé
Helicenes and extended helical π-conjugated compounds have been widely studied, but most of the systems contain only aromatic benzene or heterocyclic rings, showing local aromatic character. Herein, new S-shaped double [6]helicene 1, which has two embedded para-quinodimethane (p-QDM) units, is reported. Due to the existence of a proaromatic quinoidal substructure, it has open-shell diradical character. Its model compound, C-shaped single [6]helicene 2 containing one p-QDM unit, was also synthesized and compared. Their ground-state structures and electronic properties were systematically studied by a combination of various experimental methods assisted by theoretical calculations. Compound 1 has a double-helical structure in the crystal, with the two terminal [6]helicene units bent in opposite directions (i.e., anti form). However, an anti/syn isomerization process with a moderate interconversion energy barrier was observed on the NMR timescale. Compound 1 shows amphoteric redox behavior. It also exhibits open-shell diradical character (y
Identifiants
pubmed: 32614108
doi: 10.1002/chem.202002952
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
15613-15622Subventions
Organisme : Ministry of Education, Singapore
ID : R-143-000-692-114, MOE2018-T2-1-152, MOE2014-T3-1-004
Organisme : Ministry of Education, Singapore
ID : R-143-000-B62-114, MOE2018-T2-1-152, MOE2014-T3-1-004
Informations de copyright
© 2020 Wiley-VCH GmbH.
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