ArticleChemistry (Weinheim an der Bergstrasse, Germany)2021
Rethinking Uncaging: A New Antiaromatic Photocage Driven by a Gain of Resonance Energy.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- Heterolysis vs Homolysis andThe Journal of organic chemistry · 2026Article
- Reversible fluorenol photobases that perform CONature chemistry · 2025Article
- Inactivation of Competitive Decay Channels Leads to Enhanced Coumarin Photochemistry.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Rethinking Uncaging: A New Antiaromatic Photocage Driven by a Gain of Resonance Energy.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
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Authors and funding
7 authors.
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Abstract
Photoactivatable compounds for example photoswitches or photolabile protecting groups (PPGs, photocages) for spatiotemporal light control, play a crucial role in different areas of research. For each application, parameters such as the absorption spectrum, solubility in the respective media and/or photochemical quantum yields for several competing processes need to be optimized. The design of new photochemical tools therefore remains an important task. In this study, we exploited the concept of excited-state-aromaticity, first described by N. Colin Baird in 1971, to investigate a new class of photocages, based on cyclic, ground-state-antiaromatic systems. Several thio- and nitrogen-functionalized compounds were synthesized, photochemically characterized and further optimized, supported by quantum chemical calculations. After choosing the optimal scaffold, which shows an excellent uncaging quantum yield of 28 %, we achieved a bathochromic shift of over 100 nm, resulting in a robust, well accessible, visible light absorbing, compact new photocage with a clean photoreaction and a high quantum product (ϵ⋅Φ) of 893 M
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