Journal ArticleDOI
"Flex-activated" mechanophores: using polymer mechanochemistry to direct bond bending activation.
TLDR
Studies in mechanochemical transduction that probe the activation of bonds orthogonal to an elongated polymer main chain are described, a first step toward mechanophores capable of releasing side-chain functionalities without inherently compromising the overall macromolecular architecture.Abstract:
We describe studies in mechanochemical transduction that probe the activation of bonds orthogonal to an elongated polymer main chain. Compression of mechanophore-cross-linked materials resulted in the release of small molecules via cleavage of covalent bonds that were not integral components of the elongated polymer segments. The reactivity is proposed to arise from the distribution of force through the cross-linking units of the polymer network and subsequent bond bending motions that are consistent with the geometric changes in the overall reaction. This departure from contemporary polymer mechanochemistry, in which activation is achieved primarily by force-induced bond elongation, is a first step toward mechanophores capable of releasing side-chain functionalities without inherently compromising the overall macromolecular architecture.read more
Citations
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Multi-Stimuli Responsive Donor–Acceptor Tetraphenylethylene Substituted Benzothiadiazoles
TL;DR: In this paper, a series of symmetrical and unsymmetrical TPE substituted BTDs 3-8 were designed and synthesized by the Suzuki and Stille coupling reactions.
Journal ArticleDOI
Mechanophore activation at heterointerfaces.
TL;DR: Silica nanoparticles grafted with poly(methyl acrylate) (PMA) chains anchored by a maleimide-anthracene cycloadduct were synthesized to demonstrate mechanochemically selective activation of mechanophores at heterogeneous interfaces to test stress activation of interfacially bonded mechanophore relevant to the design of fiber-reinforced polymer composites.
Journal ArticleDOI
A Latent Mechanoacid for Time-Stamped Mechanochromism and Chemical Signaling in Polymeric Materials.
TL;DR: The post-activation kinetics of coloration are used to demonstrate a new concept in mechanochromism, namely not only a spectroscopic indicator of whether and where a mechanical event has occurred, but when it occurred.
Journal ArticleDOI
Mechanically Triggered Small Molecule Release from a Masked Furfuryl Carbonate
TL;DR: A modular mechanophore design platform for molecular release via a mechanically triggered cascade reaction that enables the decomposition and release to proceed quickly at room temperature after unmasking via mechanical force is described.
Journal ArticleDOI
Copper-catalyzed direct C-2 difluoromethylation of furans and benzofurans: access to C-2 CF2H derivatives.
TL;DR: The developed methodology allows the selective introduction of the CF2CO2Et moiety at C-2 using CuI as a catalyst, which was applied to a broad range of furans and benzofurans, giving the functionalized products in moderate to good yields.
References
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Journal ArticleDOI
Force-induced activation of covalent bonds in mechanoresponsive polymeric materials
Douglas A. Davis,Andrew Hamilton,Jinglei Yang,Jinglei Yang,Lee D. Cremar,Dara Van. Gough,Stephanie L. Potisek,Mitchell T. Ong,Paul V. Braun,Todd J. Martínez,Todd J. Martínez,Scott R. White,Jeffrey S. Moore,Nancy R. Sottos +13 more
TL;DR: It is found that pronounced changes in colour and fluorescence emerge with the accumulation of plastic deformation, indicating that in these polymeric materials the transduction of mechanical force into the ring-opening reaction is an activated process.
Journal ArticleDOI
Mechanically-induced chemical changes in polymeric materials
Mary M. Caruso,Douglas A. Davis,Qilong Shen,Susan A. Odom,Nancy R. Sottos,Scott R. White,Jeffrey S. Moore +6 more
TL;DR: The purpose of this review is to broadly survey the mechanical to chemical relationships between synthetic polymers, and to consider the I-O relationship as an energy transduction process for designing stimuli-responsive materials.
Journal ArticleDOI
Mechanochemistry: the mechanical activation of covalent bonds.
TL;DR: A survey of the classical works in mechanochemistry is given and the key mechanochemical phenomena into perspective with recent results from atomic force microscopy and quantum molecular dynamics simulations are put into perspective.
Journal ArticleDOI
From mechanism to mouse: a tale of two bioorthogonal reactions.
TL;DR: Work in the laboratory led to the development of two bioorthogonal transformations that exploit the azide as a small, abiotic, and bioinert reaction partner: the Staudinger ligation and strain-promoted azide–alkyne cycloaddition.
Journal ArticleDOI
Mechanical processes in biochemistry.
TL;DR: This review provides the conceptual framework to understand the role of mechanical force in biochemistry.