Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 38, Pages 12328-12331Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b07610
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Funding
- National Science Foundation [DMR 1307354]
- Arnold and Mabel Beckman Foundation
- Division Of Materials Research
- Direct For Mathematical & Physical Scien [1307354] Funding Source: National Science Foundation
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Transformation of naphthopyran into a colored merocyanine species in polymeric materials is achieved using mechanical force. We demonstrate that the mechanochemical reactivity of naphthopyran is critically dependent on the regiochemistry, with only one particular substitution pattern leading to successful mechanochemical activation. Two alternative regioisomers with different polymer attachment points are demonstrated to be mechanochemically inactive. This trend in reactivity is accurately predicted by DFT calculations, reinforcing predictive capabilities in mechanochemical systems. We rationalize the reactivity differences between naphthopyran regioisomers in terms of the alignment of the target C-O pyran bond with the direction of the applied mechanical force and its effect on mechanochemical transduction along the reaction coordinate.
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