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Photocyclization of Fluorinated Acetophenones Unlocks an Efficient Way to Solar Energy Storage
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2024-11-18 , DOI: 10.1021/jacs.4c12249
Henning Maag, Matthias Schmitz, Alexander Sandvoß, Domenik Mundil, Abhilash Pedada, Felix Glaser, Christoph Kerzig, Johannes M. Wahl

The ability to store and release energy efficiently is crucial for advancing sustainable energy technologies, and light-driven molecular isomerization presents a promising solution. However, a persistent challenge in this field is achieving both high stability of the energy-storing photoisomer and establishing efficient catalysis for back-isomerization, a critical process for releasing the stored energy as heat. In this work, we introduce a conceptually new molecular system designed for long-term energy storage, which is based on the reversible isomerization of ortho-methylacetophenone ⇄ benzocyclobutenol. Key to the success of this system is the strategic placement of a trifluoromethyl group, which enhances the overall performance by preventing unwanted side reactions during photochemical cyclization and by increasing the stability of the benzocyclobutenol moiety. Back isomerization is established using simple organic bases as catalysts, taking advantage of significant rate differences between normal and anionic electrocyclic ring-openings. This approach allows for controlled and predictable heat release under ambient conditions, positioning this molecular pair as a promising candidate for practical energy storage solutions.

中文翻译:


氟化苯乙酮的光环化为太阳能储存提供了一种有效的方法



有效储存和释放能量的能力对于推进可持续能源技术至关重要,而光驱动的分子异构化提供了一种很有前途的解决方案。然而,该领域的一个持续挑战是实现储能光异构体的高稳定性和建立反向异构化的有效催化,这是将储存的能量作为热量释放的关键过程。在这项工作中,我们引入了一种概念上设计用于长期能量存储的新型分子系统,该系统基于甲基苯乙酮⇄苯并环丁烯醇的可逆异构化。该系统成功的关键是三氟甲基基团的战略布局,它通过防止光化学环化过程中不需要的副反应和增加苯并环丁烯醇部分的稳定性来提高整体性能。使用简单的有机碱作为催化剂建立反异构化,利用正常和阴离子电循环开环之间的显着速率差异。这种方法允许在环境条件下进行受控和可预测的热量释放,使该分子对成为实际储能解决方案的有前途的候选者。
更新日期:2024-11-19
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