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Regioisomer-Specific Mechanochromism of Naphthopyran in Polymeric Materials

Robb, Maxwell J. and Kim, Tae Ann and Halmes, Abigail J. and White, Scott R. and Sottos, Nancy R. and Moore, Jeffrey S. (2016) Regioisomer-Specific Mechanochromism of Naphthopyran in Polymeric Materials. Journal of the American Chemical Society, 138 (38). pp. 12328-12331. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20180605-134324241

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Abstract

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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/jacs.6b07610DOIArticle
https://pubs.acs.org/doi/suppl/10.1021/jacs.6b07610PublisherSupporting Information
ORCID:
AuthorORCID
Robb, Maxwell J.0000-0002-0528-9857
Kim, Tae Ann0000-0002-1084-638X
White, Scott R.0000-0002-0831-9097
Sottos, Nancy R.0000-0002-5818-520X
Additional Information:© 2016 American Chemical Society. Received: July 22, 2016; Published: September 12, 2016. This work was supported in part by the National Science Foundation (DMR 1307354). M.J.R. gratefully acknowledges the Arnold and Mabel Beckman Foundation for a Beckman Institute Postdoctoral Fellowship. The authors declare no competing financial interest.
Funders:
Funding AgencyGrant Number
NSFDMR-1307354
Arnold and Mabel Beckman FoundationUNSPECIFIED
Issue or Number:38
Record Number:CaltechAUTHORS:20180605-134324241
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20180605-134324241
Official Citation:Regioisomer-Specific Mechanochromism of Naphthopyran in Polymeric Materials. Maxwell J. Robb, Tae Ann Kim, Abigail J. Halmes, Scott R. White, Nancy R. Sottos, and Jeffrey S. Moore. Journal of the American Chemical Society 2016 138 (38), 12328-12331. DOI: 10.1021/jacs.6b07610
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:86798
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:05 Jun 2018 21:39
Last Modified:09 Mar 2020 13:18

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