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Tunable Photoswitching in Norbornadiene (NBD)/Quadricyclane (QC) – Fullerene Hybrids
Author(s) -
Lorenz Patrick,
Wullschläger Florian,
Rüter Antonia,
Meyer Bernd,
Hirsch Andreas
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202102109
Subject(s) - quadricyclane , moiety , fullerene , norbornadiene , linker , chemistry , cycloaddition , covalent bond , materials science , photochemistry , stereochemistry , organic chemistry , computer science , operating system , catalysis
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 C 60 . 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–C 60 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.