Issue 40, 2023

Driving the quadricyclane-to-norbornadiene isomerization by charge separation with perylenediimide as electron acceptor

Abstract

Through comprehensive photo-assays, this study investigates the reaction coordinate governing the interconversion between quadricyclane (QC) and norbornadiene (NBD) upon photo-irradiation up to a wavelength of 550 nm. To harness this spectroscopic range for energy release, we link the NBD-core with a highly electron-accepting perylenediimide (PDI) with broad absorption, achieving strong electronic coupling between them. We detail the successful synthesis and present extensive DFT calculations to determine the amount of stored energy. By means of transient absorption spectroscopy, an oxidative electron transfer is observed during the QC-to-NBD isomerization following the initial PDI photoexcitation. This charge-separated state is key to triggering the back-isomerization with visible light excitation.

Graphical abstract: Driving the quadricyclane-to-norbornadiene isomerization by charge separation with perylenediimide as electron acceptor

Supplementary files

Article information

Article type
Edge Article
Submitted
18 Jul 2023
Accepted
18 Sep 2023
First published
20 Sep 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2023,14, 11096-11104

Driving the quadricyclane-to-norbornadiene isomerization by charge separation with perylenediimide as electron acceptor

W. Zika, A. Leng, R. Weiß, S. Pintér, C. M. Schüßlbauer, T. Clark, A. Hirsch and D. M. Guldi, Chem. Sci., 2023, 14, 11096 DOI: 10.1039/D3SC03679K

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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