A backbone lever-arm effect enhances polymer mechanochemistry

Nature Chemistry

Volumn 5, Issue 2, 2013, Pages 110-114

  Klukovich, Hope M ^a   Kouznetsova, Tatiana B ^a   Kean, Zachary S ^a   Lenhardt, Jeremy M ^a   Craig, Stephen L ^a  

^a DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE DERIVATIVE; ELASTOMER; PLASTIC; POLYBUTADIENE; POLYNORBORNEN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; MECHANICS; METHODOLOGY; SPECTROSCOPY;

BUTADIENES; COMPUTER SIMULATION; ELASTOMERS; MECHANICS; MOLECULAR STRUCTURE; PLASTICS; SPECTRUM ANALYSIS;

MLCS; MLOWN;

EID: 84873806958     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.1540     Document Type: Article

References (46)

1. Hickenboth, C. R. et al. Biasing reaction pathways with mechanical force. Nature 446, 423-427 (2007
2. Lenhardt, J. M. et al. Reactive cross-Talk between adjacent tension-Trapped transition states. J. Am. Chem. Soc. 113, 3222-3225 (2011
3. Lenhardt, J. M. et al. Trapping a diradical transition state by mechanochemical polymer extension. Science 329, 1057-1060 (2010
4. Brantley, J. N., Wiggins, K. M. & Bielawaski, C. W. Unclicking the click: Mechanically facilitated 1,3-dipolar cycloreversions. Science 333, 1606-1609 (2011
5. Wiggins, K. M. & Bielawaski, C. W. A mechanochemical approach to deracemization. Angew. Chem. Int. Ed. 51, 1640-1643 (2012
6. Piermattei, A., Karthikeyan, S. & Sijbesma, R. P. Activating catalysts with mechanical force. Nature Chem. 1, 133-137 (2009
7. Davis, D. A. et al. Force-induced activation of covalent bonds in mechanoresponsive polymeric materials. Nature 459, 68-72 (2009
8. Chen, Y. et al. Mechanically induced chemiluminescence from polymers incorporating a 1,2-dioxetane unit in the main chain. Nature Chem. 4, 559-562 (2012
9. Black, A. L., Lenhardt, J. M. & Craig, S. L. From molecular mechanochemistry to stress-responsive materials. J. Mater. Chem. 21, 1655-1663 (2011
10. Black, A. L., Orlicki, J. A. & Craig, S. L. Mechanochemically triggered bond formation in solid-state polymers. J. Mater. Chem. 21, 8460-8465 (2011
11. Caruso, M. M. et al. Mechanically-induced chemical changes in polymeric materials. Chem. Rev. 109, 5755-5798 (2009
12. Lenhardt, J. M. et al. Characterizing the mechanochemically active domains in gem-dihalocyclopropanated polybutadiene under compression and tension. J. Mater. Chem. 21, 8454-8459 (2011
13. Tian, Y. & Boulatov, R. Quantum-Chemical validation of the local assumption of chemomechanics for a unimolecular reaction. ChemPhysChem 13, 2277-2281 (2012
14. Ribas-Arino, J., Shiga, M. & Marx, D. Mechanochemical transduction of externally applied forces to mechanophores. J. Am. Chem. Soc. 132, 10609-10614 (2010
15. Kryger, M. J., Munaretto, A. M. & Moore, J. S. Structure- mechanochemical activity relationships for cyclobutane mechanophores. J. Am. Chem. Soc. 133, 18992-18998 (2011
16. Lenhardt, J. M., Black, A. L. & Craig, S. L. gem- Dichlorocyclopropanes as abundant and efficient mechanophores in polybutadiene copolymers under mechanical stress. J. Am. Chem. Soc. 131, 10818-10819 (2009
17. Brantley, J. N., Konda, S. S. M., Makarov, D. E. & Bielawaski, C. W. Regiochemical effects on molecular stability: A mechanochemical evaluation of 1,4- And 1,5-disubstituted triazoles. J. Am. Chem. Soc. 134, 9882-9885 (2012
18. Yang, Q-Z. et al. A molecular force probe. Nature Nanotech. 4, 302-306 (2009
19. Sheiko, S. S. et al. Adsorption-induced scission of carbon-Carbon bonds. Nature 440, 191-194 (2006
20. Ong, M. T., Leiding, J., Tao, H., Virshup, A. & Martinez, T. J. First principles dynamics and minimum energy pathways for mechanochemical ring opening of cyclobutene. J. Am. Chem. Soc. 131, 6377-6379 (2009
21. Ribas-Arino J., Shiga M. & Marx D. Understanding covalent mechanochemistry. Angew. Chem. Int. Ed. 48, 4190-4193 (2009
22. Konda, S. S. M., Brantley, J. N., Bielawaski, C. W. & Makarov, D. E. Chemical reactions modulated by mechanical stress: Extended Bell theory. J. Chem. Phys. 135, 164103 (2011
23. Garcia-manyes, S., Liang, J., Szoszkiewicz, R., Kuo, T-L. & Fernandez, J. M. Force-Activated reactivity switch in a bimolecular chemical reaction. Nature Chem. 1, 236-242 (2009
24. Alegre-Cebollada, J., Kosuri, P., Rivas-Pardo, J. A. & Fernandez, J. M. Direct observation of disulfide isomerization in a single protein. Nature Chem. 3, 882-887 (2011
25. Garcia-manyes, S., Kuo, T-L. & Fernandez, J. M. Contrasting the individual reactive pathways in protein unfolding and disulfide bond reduction observed within a single protein. J. Am. Chem. Soc. 133, 3104-3113 (2011
26. Kersey, F. R., Yount, W. C. & Craig, S. L. Single-molecule force spectroscopy of bimolecular reactions: System homology in the mechanical activation of ligand substitution reactions. J. Am. Chem. Soc. 128, 3886-3887 (2006
27. Wu, D., Lenhardt, J. M., Black, A. L., Akhremitchev, B. B. & Craig, S. L. Molecular stress relief through a force-induced irreversible extension in polymer contour length. J. Am. Chem. Soc. 132, 15936-15938 (2010
28. Akbulatov, S., Tian, Y. & Boulatov, R. Force-reactivity property of a single monomer is sufficient to predict the micromechanical behavior of its polymer. J. Am. Chem. Soc. 134, 7620-7623 (2012
29. Dopieralski, P. et al. On the role of polymer chains in transducing external mechanical forces to benzocyclobutene mechanophores. J. Mater. Chem. 21, 8309-8316 (2011
30. Ribas-Arino, J., Shiga, M. & Marx, D. Mechanochemical transduction of externally applied forces to mechanophores. J. Am. Chem. Soc. 132, 10609-10614 (2010
31. Klukovich, H. M. et al. Tension trapping of carbonyl ylides facilitated by a change in polymer backbone. J. Am. Chem. Soc. 134, 9577-9580 (2012
32. Oberhauser, A. F., Marszalek, P. E., Erickson, H. P. & Fernandez, J. M. Polysaccharide elasticity governed by chair-boat transitions of the glucopyranose ring. Nature 393, 181-185 (1998
33. Evans, E. & Ritchie, K. Dynamic strength of molecular adhesion bonds. Biophys. J. 72, 1541-1555 (1997
34. Evans, E. Probing the relation between force lifetime and chemistry in single molecular bonds. Annu. Rev. Biophys. Biomol. Struct. 30, 105-128 (2001
35. Ray, C., Brown, J. R. & Akhremitchev, B. B. Correction of systematic errors in single-molecule force spectroscopy with polymeric tethers by atomic force microscopy. J. Phys. Chem. B 111, 1963-1974 (2007
36. Dobrynin, A. V., Carrillo, J-m. Y. & Rubinstein, M. Chains are more flexible under tension. Macromolecules 43, 9181-9190 (2010
37. Duffey, D. C., Minyard, J. P. & Lane, R. H. Thermal rearrangement of 1,1-dibromo-Cis-2,3-dimethylcyclopropane. J. Org. Chem. 31, 3865-3867 (1966
38. Faza, O. N., Lopez, C. S., Alvarez, R. & de Lera, A. R. Solvolytic ring opening reactions of cyclopropyl bromides. An assessment of the Woodward-Hoffmann-dePuy rule. J. Org. Chem. 69, 9002-9010 (2004
39. Boulatov, R. Reaction dynamics in the formidable gap. Pure Appl. Chem. 83, 25-41 (2011
40. Hummer, G. & Szabo, A. Free energy profiles from single-molecule pulling experiments. Proc. Natl Acad. Sci. USA 107, 21441-21445 (2010
41. Hummer, G. & Szabo, A. Kinetics from nonequilibrium single-molecule pulling experiments. Biophys. J. 85, 5-15 (2003
42. Dudko, O. K., Hummer, G. & Szabo, A. Intrinsic rates and activation free energies from single-molecule pulling experiments. Phys. Rev. Lett. 96, 108101 (2006
43. Wiita, A. P., Ainavarapu, S. R. K., Huang, H. H. & Fernandez, J. M. Forcedependent chemical kinetics of disulfide bond reduction observed with singlemolecule techniques. Proc. Natl Acad. Sci. USA 103, 7222-7227 (2006
44. Huang, Z. et al. Method to derive restoring forces of strained molecules from kinetic measurments. J. Am. Chem. Soc. 131, 1407-1409 (2009
45. Dopieralski, P., Ribas-Arino, J. & Marx, D. Force-Transformed free-energy surfaces and trajectory-shooting simulations reveal the mechanostereochemistry of cyclopropane ring-opening reactions. Angew. Chem. Int. Ed. 7105-7108 (2011
46. Beyer, M. K. The mechanical strength of a covalent bond calculated by density functional theory. J. Chem. Phys. 112, 7307-7312 (2000