Synthesis and photoinduced switching properties of C7-heteroatom containing push–pull norbornadiene derivatives

Krappmann D, Hirsch A (2025)

Publication Type: Journal article

Publication year: 2025

Journal

Beilstein Journal of Organic Chemistry Beilstein-Institut

Book Volume: 21

Pages Range: 807-816

DOI: 10.3762/bjoc.21.64

Abstract

We report the synthesis and characterization of heteroatom-incorporated norbornadiene (NBD) derivatives. Push–pull substitution on the 2 and 3 position as well as introduction of oxygen or nitrogen at position 7 of the NBD scaffold have led to the development of a new family of photoswitches. We studied the potential conversion of norbornadiene to quadricyclane (QC) isomers. As main investigation tools, UV–vis and NMR spectroscopy were utilized. We determined significant spectral features of the formed NBD species, including λmax and λonset values, all of which exhibit redshifts compared to their isocyclic counterparts. Additionally, the selected QC isomers were subjected to thermal and catalytic back-conversion studies.

Authors with CRIS profile

Daniel Krappmann Lehrstuhl für Organische Chemie II Andreas Hirsch Lehrstuhl für Organische Chemie II

How to cite

APA:

Krappmann, D., & Hirsch, A. (2025). Synthesis and photoinduced switching properties of C7-heteroatom containing push–pull norbornadiene derivatives. Beilstein Journal of Organic Chemistry, 21, 807-816. https://doi.org/10.3762/bjoc.21.64

MLA:

Krappmann, Daniel, and Andreas Hirsch. "Synthesis and photoinduced switching properties of C7-heteroatom containing push–pull norbornadiene derivatives." Beilstein Journal of Organic Chemistry 21 (2025): 807-816.

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