Molecular engineering of mechanophore activity for stress-responsive polymeric materials

Molecular-level design principles by which to engineer enhanced mechanophore activity are reviewed, with an emphasis on quantitative structure–activity studies determined for a family of gem-dihalocyclopropane mechanophores.

[1]  J. Schwartz,et al.  Organometallics , 1987, Science.

[2]  Arnold L. Rheingold,et al.  Stress-responsive polymers containing cyclobutane core mechanophores: reactivity and mechanistic insights. , 2013, Journal of the American Chemical Society.

[3]  R. Boulatov.  Reaction dynamics in the formidable gap , 2010 .

[4]  Paul V Braun,et al.  Force-induced redistribution of a chemical equilibrium. , 2010, Journal of the American Chemical Society.

[5]  B. Akhremitchev,et al.  Molecular stress relief through a force-induced irreversible extension in polymer contour length. , 2010, Journal of the American Chemical Society.

[6]  J. Orlicki,et al.  Mechanochemically triggered bond formation in solid-state polymers , 2011 .

[7]  M. Beyer,et al.  The mechanical strength of a covalent bond calculated by density functional theory , 2000 .

[8]  R. Sijbesma,et al.  Mechanocatalytic Polymerization and Cross-Linking in a Polymeric Matrix. , 2013, ACS macro letters.

[9]  Johnathan N. Brantley,et al.  Regiochemical effects on molecular stability: a mechanochemical evaluation of 1,4- and 1,5-disubstituted triazoles. , 2012, Journal of the American Chemical Society.

[10]  Dmitrii E Makarov,et al.  Chemical reactions modulated by mechanical stress: extended Bell theory. , 2011, The Journal of chemical physics.

[11]  Jeremy M. Lenhardt,et al.  From molecular mechanochemistry to stress-responsive materials , 2011 .

[12]  Jeffrey S. Moore,et al.  Shear activation of mechanophore-crosslinked polymers , 2011 .

[13]  S. Craig,et al.  Single-molecule force spectroscopy of bimolecular reactions: system homology in the mechanical activation of ligand substitution reactions. , 2006, Journal of the American Chemical Society.

[14]  Andrew J Boydston,et al.  Successive mechanochemical activation and small molecule release in an elastomeric material. , 2014, Journal of the American Chemical Society.

[15]  Christopher W. Bielawski,et al.  Molecular catch bonds and the anti-Hammond effect in polymer mechanochemistry. , 2013, Journal of the American Chemical Society.

[16]  E. Uggerud,et al.  Ring opening vs. direct bond scission of the chain in polymeric triazoles under the influence of an external force. , 2012, Chemical communications.

[17]  E. W. Meijer,et al.  Mechanically induced chemiluminescence from polymers incorporating a 1,2-dioxetane unit in the main chain. , 2012, Nature chemistry.

[18]  K. Tashiro,et al.  Morphological effect on the Raman frequency shift induced by tensile stress applied to crystalline polyoxymethylene and polyethylene: spectroscopic support for the idea of an inhomogeneous stress distribution in polymer material , 1988 .

[19]  Jason R. Brown,et al.  Correction of systematic errors in single-molecule force spectroscopy with polymeric tethers by atomic force microscopy. , 2007, The journal of physical chemistry. B.

[20]  T. Martínez,et al.  Masked cyanoacrylates unveiled by mechanical force. , 2010, Journal of the American Chemical Society.

[21]  R. Sijbesma,et al.  Activating catalysts with mechanical force. , 2009, Nature chemistry.

[22]  Andrew J. Boydston,et al.  "Flex-activated" mechanophores: using polymer mechanochemistry to direct bond bending activation. , 2013, Journal of the American Chemical Society.

[23]  E. Evans.  Probing the relation between force--lifetime--and chemistry in single molecular bonds. , 2001, Annual review of biophysics and biomolecular structure.

[24]  Xuanhe Zhao,et al.  Mechanochemical Activation of Covalent Bonds in Polymers with Full and Repeatable Macroscopic Shape Recovery. , 2014, ACS macro letters.

[25]  R. Rosenfeld.  Nature , 2009, Otolaryngology--head and neck surgery : official journal of American Academy of Otolaryngology-Head and Neck Surgery.

[26]  Mitchell T. Ong,et al.  Force-induced activation of covalent bonds in mechanoresponsive polymeric materials , 2009, Nature.

[27]  S. Craig,et al.  Mechanochemical remodeling of synthetic polymers , 2012 .

[28]  R. Sijbesma,et al.  Mechanical activation of a latent olefin metathesis catalyst and persistence of its active species in ROMP , 2012 .

[29]  H. Clausen‐Schaumann,et al.  Mechanochemistry: the mechanical activation of covalent bonds. , 2005, Chemical reviews.

[30]  Mary M. Caruso,et al.  Mechanically-induced chemical changes in polymeric materials. , 2009, Chemical reviews.

[31]  Jeffrey S. Moore,et al.  Proton-coupled mechanochemical transduction: a mechanogenerated acid. , 2012, Journal of the American Chemical Society.

[32]  Gerhard Hummer,et al.  Kinetics from nonequilibrium single-molecule pulling experiments. , 2003, Biophysical journal.

[33]  Nancy R. Sottos,et al.  Biasing reaction pathways with mechanical force , 2007, Nature.

[34]  D. Marx,et al.  Force-transformed free-energy surfaces and trajectory-shooting simulations reveal the mechano-stereochemistry of cyclopropane ring-opening reactions. , 2011, Angewandte Chemie.

[35]  T. Martínez,et al.  Inducing and quantifying forbidden reactivity with single-molecule polymer mechanochemistry. , 2014, Nature chemistry.

[36]  J. Lenhardt,et al.  gem-Dichlorocyclopropanes as abundant and efficient mechanophores in polybutadiene copolymers under mechanical stress. , 2009, Journal of the American Chemical Society.

[37]  Ramesh Talreja,et al.  Fatigue damage mechanisms in unidirectional carbon-fibre-reinforced plastics , 1999 .

[38]  D. Marx,et al.  Understanding covalent mechanochemistry. , 2009, Angewandte Chemie.

[39]  Gerhard Hummer,et al.  Intrinsic rates and activation free energies from single-molecule pulling experiments. , 2006, Physical review letters.

[40]  R. Lane,et al.  Thermal Rearrangement of 1,1-Dibromo-cis-2,3-dimethylcyclopropane , 1966 .

[41]  R. Sijbesma,et al.  Performance of Mechanochemically Activated Catalysts Is Enhanced by Suppression of the Thermal Effects of Ultrasound. , 2012, ACS macro letters.

[42]  W. Krause,et al.  Mechanochemical strengthening of a synthetic polymer in response to typically destructive shear forces. , 2013, Nature chemistry.

[43]  Scott R White,et al.  Mechanophore-linked addition polymers. , 2007, Journal of the American Chemical Society.

[44]  Jeffrey S. Moore,et al.  Structure-mechanochemical activity relationships for cyclobutane mechanophores. , 2011, Journal of the American Chemical Society.

[45]  Mitchell T. Ong,et al.  Trapping a Diradical Transition State by Mechanochemical Polymer Extension , 2010, Science.

[46]  J. Lenhardt,et al.  A backbone lever-arm effect enhances polymer mechanochemistry. , 2013, Nature chemistry.

[47]  S. Craig,et al.  Mechanically induced scission and subsequent thermal remending of perfluorocyclobutane polymers. , 2011, Journal of the American Chemical Society.

[48]  D. Marx,et al.  Mechanochemical transduction of externally applied forces to mechanophores. , 2010, Journal of the American Chemical Society.

[49]  Xiangqian Hu,et al.  Tension trapping of carbonyl ylides facilitated by a change in polymer backbone. , 2012, Journal of the American Chemical Society.

[50]  T. Martínez,et al.  First principles dynamics and minimum energy pathways for mechanochemical ring opening of cyclobutene. , 2009, Journal of the American Chemical Society.

[51]  Jeffrey S. Moore,et al.  Environmental effects on mechanochemical activation of spiropyran in linear PMMA , 2011 .

[52]  Jeffrey S. Moore,et al.  Characterizing the mechanochemically active domains in gem-dihalocyclopropanated polybutadiene under compression and tension , 2011 .

[53]  R. Boulatov,et al.  Quantum-chemical validation of the local assumption of chemomechanics for a unimolecular reaction. , 2012, Chemphyschem : a European journal of chemical physics and physical chemistry.

[54]  R. Álvarez,et al.  Solvolytic ring-opening reactions of cyclopropyl bromides. An assessment of the Woodward-Hoffmann-DePuy rule. , 2004, The Journal of organic chemistry.