Proton-coupled mechanochemical transduction: A mechanogenerated acid

Charles E. Diesendruck; Brian D. Steinberg; Naoto Sugai; Meredith N. Silberstein; Nancy R. Sottos; Scott R. White; Paul V. Braun; Jeffrey S. Moore

doi:10.1021/ja305645x

Proton-coupled mechanochemical transduction: A mechanogenerated acid

Charles E. Diesendruck, Brian D. Steinberg, Naoto Sugai, Meredith N. Silberstein, Nancy R. Sottos, Scott R. White, Paul V. Braun, Jeffrey S. Moore

Research output: Contribution to journal › Article › peer-review

Abstract

A novel mechanophore with acid-releasing capability is designed to produce a simple catalyst for chemical change in materials under mechanical stress. The mechanophore, based on a gem-dichlorocyclopropanated indene, is synthesized and used as a cross-linker in poly(methyl acrylate). Force-dependent rearrangement is demonstrated for cross-linked mechanophore samples loaded in compression, while the control shows no significant response. The availability of the released acid is confirmed by exposing a piece of insoluble compressed polymer to a pH indicator solution. The development of this new mechanophore is the first step toward force-induced remodeling of stressed polymeric materials utilizing acid-catalyzed cross-linking reactions.

Original language	English (US)
Pages (from-to)	12446-12449
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	134
Issue number	30
DOIs	https://doi.org/10.1021/ja305645x
State	Published - Aug 1 2012

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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abstract = "A novel mechanophore with acid-releasing capability is designed to produce a simple catalyst for chemical change in materials under mechanical stress. The mechanophore, based on a gem-dichlorocyclopropanated indene, is synthesized and used as a cross-linker in poly(methyl acrylate). Force-dependent rearrangement is demonstrated for cross-linked mechanophore samples loaded in compression, while the control shows no significant response. The availability of the released acid is confirmed by exposing a piece of insoluble compressed polymer to a pH indicator solution. The development of this new mechanophore is the first step toward force-induced remodeling of stressed polymeric materials utilizing acid-catalyzed cross-linking reactions.",

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AU - Diesendruck, Charles E.

AU - Steinberg, Brian D.

AU - Sugai, Naoto

AU - Silberstein, Meredith N.

AU - Sottos, Nancy R.

AU - White, Scott R.

AU - Braun, Paul V.

AU - Moore, Jeffrey S.

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AB - A novel mechanophore with acid-releasing capability is designed to produce a simple catalyst for chemical change in materials under mechanical stress. The mechanophore, based on a gem-dichlorocyclopropanated indene, is synthesized and used as a cross-linker in poly(methyl acrylate). Force-dependent rearrangement is demonstrated for cross-linked mechanophore samples loaded in compression, while the control shows no significant response. The availability of the released acid is confirmed by exposing a piece of insoluble compressed polymer to a pH indicator solution. The development of this new mechanophore is the first step toward force-induced remodeling of stressed polymeric materials utilizing acid-catalyzed cross-linking reactions.

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Proton-coupled mechanochemical transduction: A mechanogenerated acid

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