Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 143, Issue 21, Pages 7925-7929Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.1c03865
Keywords
-
Categories
Funding
- Caltech
- NSF Graduate Research Fellowship [DGE-1745301]
Ask authors/readers for more resources
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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available