Tunable Photoswitching in Norbornadiene (NBD)/Quadricyclane (QC) - Fullerene Hybrids.
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ABSTRACT: With respect to molecular switches, initializing the quadricyclane (QC) to norbornadiene (NBD) back-reaction by light is highly desirable. Our previous publication provided a unique solution for this purpose by utilizing covalently bound C60 . In this work, the fundamental processes within these hybrids has been investigated. Variation of the linker unit connecting the NBD/QC moiety with the fullerene core is used as a tool to tune the properties of the resulting hybrids. Utilizing the Prato reaction, two unprecedented NBD/QC - fullerene hybrids having a long-rigid and a short-rigid linker were synthesized. Molecular dynamics simulations revealed that this results in an average QC-C60 distance of up to 14.2 Å. By comparing the NBD-QC switching of these derivatives with the already established one having a flexible linker, valuable mechanistic insights were gained. Most importantly, spatial convergence of the QC moiety and the fullerene core is inevitable for an efficient back-reaction.
SUBMITTER: Lorenz P
PROVIDER: S-EPMC8596871 | biostudies-literature |
REPOSITORIES: biostudies-literature
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