Reversible Photoinduced Conversion of Unprecedented Norbornadiene-Based Photoswitches with Redox-Active Naphthalene Diimide Functionalities.
energy conversion
molecular photoswitches
naphthalene diimide
norbornadiene
quadricyclane
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
22 Sep 2022
22 Sep 2022
Historique:
received:
10
05
2022
pubmed:
2
7
2022
medline:
2
7
2022
entrez:
1
7
2022
Statut:
ppublish
Résumé
An unprecedented compound class of functional organic hybrids consisting of a photoswitchable norbornadiene building block and a redoxactive chromophore, namely naphthalene diimide, were designed and synthesized. Within these structures the capability of rylene chromophores to function as a redox active catalyst upon their photoexcitation was utilized to initiate the oxidative back-conversion of the in situ formed quadricyclane unit to its norbornadiene analogue. In this way successive photoexcitation at two different wavelengths enabled a controlled photoswitching between the two isomerical states of the hybrids. Beyond this prove of concept, the dependency of the reaction rate to the intramolecular distance of the two functional molecular building blocks as well as the concentration of the photoexcited sample was monitored. The experimental findings and interpretations were furthermore supported by quantum chemical investigations.
Identifiants
pubmed: 35776126
doi: 10.1002/chem.202201446
pmc: PMC9796843
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202201446Subventions
Organisme : Deutsche Forschungsgemeinschaft
ID : 391585168 "Photochemisch und magnetochemisch ausgelöste Speicherung/Freisetzung von Sonnenergie in gespannten organischen Verbindungen".
Informations de copyright
© 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
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