期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 143, 期 21, 页码 7925-7929出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.1c03865
关键词
-
资金
- Caltech
- NSF Graduate Research Fellowship [DGE-1745301]
The discovery of a 2H-naphtho[1,2-b]pyran mechanophore that produces a permanent merocyanine dye upon mechanochemical activation is reported. The irreversible nature of the mechanically generated merocyanine is attributed to a unique reaction involving the scission of an ester C-O bond. This permanent coloration offers new opportunities for sensing, force-recording applications, and fundamental studies.
We report the discovery of a 2H-naphtho[1,2-b]pyran mechanophore that produces a permanent merocyanine dye upon mechanochemical activation, in contrast to the reversible product generated photochemically. Experiments suggest that the irreversibility of the mechanically generated merocyanine is due to a unique reaction in which the scission of an ester C-O bond reveals a beta-hydroxy ketone that locks the merocyanine through an intramolecular H-bonding interaction. In addition to demonstrating the reactivity using solution-phase ultrasonication, permanent merocyanine generation is also achieved in solid polymeric materials. The permanent coloration achieved with the naphthopyran mechanophore affords unique opportunities for sensing and force-recording applications as well as fundamental studies limited by the reversibility of typical colorimetric force probes.
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