Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 42, Pages 18532-18536Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202007989
Keywords
acid-base equilibria; azulene; diarylethene; negative photochromism; photochemistry
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Funding
- Max Planck Society
- EC through the Marie Sklodowska-Curie ITN project iSwitch [GA-642196]
- German Research Foundation (DFG via SFB951) [182087777]
- Studienstiftung des deutschen Volkes
- Projekt DEAL
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Proton-responsive photochromic molecules are attractive for their ability to react on non-invasive rapid optical stimuli and the importance of protonation/deprotonation processes in various fields. Conventionally, their acidic/basic sites are on hetero-atoms, which are orthogonal to the photo-active pi-center. Here, we incorporate azulene, an acid-sensitive pure hydrocarbon, into the skeleton of a diarylethene-type photoswitch. The latter exhibits a novel proton-gated negative photochromic ring-closure and its optical response upon protonation in both open and closed forms is much more pronounced than those of diarylethene photoswitches with hetero-atom based acidic/basic moieties. The unique behavior of the new photoswitch can be attributed to direct protonation on its pi-system, supported by(1)H NMR and theoretical calculations. Our results demonstrate the great potential of integrating non-alternant hydrocarbons into photochromic systems for the development of multi-responsive molecular switches.
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