Stringing the Perylene Diimide Bow.
contorted aromatics
optoelectronic materials
organic electronics
perylene diimides
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:
17 Aug 2020
17 Aug 2020
Historique:
received:
06
04
2020
revised:
29
05
2020
pubmed:
5
6
2020
medline:
5
6
2020
entrez:
5
6
2020
Statut:
ppublish
Résumé
This study explores a new mode of contortion in perylene diimides where the molecule is bent, like a bow, along its long axis. These bowed PDIs were synthesized through a facile fourfold Suzuki macrocyclization with aromatic linkers and a tetraborylated perylene diimide that introduces strain and results in a bowed structure. By altering the strings of the bow, the degree of bending can be controlled from flat to highly bent. Through spectroscopy and quantum chemical calculations, it is demonstrated that the energy of the lowest unoccupied orbital can be controlled by the degree of bending in the structures and that the energy of the highest occupied orbital can be controlled to a large extent by the constitution of the aromatic linkers. The important finding is that the bowing results not only in red-shifted absorptions but also more facile reductions.
Identifiants
pubmed: 32495388
doi: 10.1002/anie.202004989
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
14303-14307Subventions
Organisme : U.S. Department of Energy
ID : DE-SC0014563
Organisme : National Natural Science Foundation of China-Yunnan Joint Fund
ID : 21772123
Organisme : National Natural Science Foundation of China-Yunnan Joint Fund
ID : 21761142011
Organisme : National Natural Science Foundation of China-Yunnan Joint Fund
ID : 51502173
Organisme : Shanghai Government
ID : 18DZ2254200
Organisme : Shanghai Government
ID : 18JC1412900
Informations de copyright
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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Deposition Numbers 1991412 (for 1a), 1991413 (for 1b), 1991414 (for 1c) and 2006155 (for 1d) contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service www.ccdc.cam.ac.uk/structures.