Citation Link: https://doi.org/10.1002/EJOC.202401090
Gilding the Lily: Studies on the Effects of Successive Loading of Light Energy‐Storing Molecules with Norbornadiene Units
Publication Type
Article
Subjects
Norbornadiene
Chemistry
Molecule
Botany
Organic chemistry
Date Issued
2024
Abstract
The photochromic norbornadiene‐quadricyclane cycle has emerged as a promising basis for molecular solar thermal (MOST) energy storage. In this context, it has been established that multifunctional photoswitches with several norbornadiene units at one central aromatic core have favorable photochemical properties and storage capacities. Nevertheless, a maximum number of three norbornadiene units has been combined in one molecule, so far. In this work, scope and limits of this approach should be further assessed. Thus, exemplary polyfunctionalized derivatives have been synthesized by Suzuki‐Miyaura reactions, and their suitability for MOST applications was investigated. These compounds were converted into the corresponding quadricyclanes by direct UV irradiation ( λ ex =315 nm) with moderate quantum yields, whereas the reaction is more efficient upon irradiation with λ ex =520 nm in the presence of photosensitizers. But these molecules showed low stabilities and short half‐lives of 1 to 2 days. Moreover, the photochemical reaction is hampered by the close vicinity of photoactive units. Therefore, it appears that in such assemblies, a maximum number of three norbornadiene units is the limit to keep the optimal balance of photochemical properties required for MOST applications.
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