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Updated: Jul 12, 2025

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
Published on: November 29, 2018
Driving the quadricyclane-to-norbornadiene isomerization by charge separation with perylenediimide as electron
Wiebke Zika1, Andreas Leng2, René Weiß1
1Department of Physical Chemistry I, Friedrich-Alexander-Universität Egerlandstraße 3 91058 Erlangen Germany dirk.guldi@fau.de.
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.
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