Cellulose nanocrystals as chiral inducers: Enantioselective catalysis and transmission electron microscopy 3D characterization

Journal of the American Chemical Society

Volumn 137, Issue 19, 2015, Pages 6124-6127

  Kaushik, Madhu ^a   Basu, Kaustuv ^a   Benoit, Charles ^a   Cirtiu, Ciprian M ^a,b   Vali, Hojatollah ^a   Moores, Audrey ^a  

^a MCGILL UNIVERSITY   (Canada)

^b INSTITUT NATIONAL DE SANTÉ PUBLIQUE DU QUÉBEC   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CELLULOSE; CELLULOSE DERIVATIVES; CHEMICAL INDUSTRY; ELECTRON MICROSCOPES; ELECTRON MICROSCOPY; ENANTIOSELECTIVITY; KETONES; PALLADIUM; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CELLULOSE NANO-CRYSTALS; CELLULOSE NANOCRYSTAL (CNCS); CRYO-ELECTRON MICROSCOPY; ENANTIOMERIC EXCESS; ENANTIOSELECTIVE CATALYSIS; FINE CHEMICAL INDUSTRY; SUSTAINABLE SOLUTION; TECHNOLOGICAL CHALLENGES;

HIGH RESOLUTION TRANSMISSION ELECTRON MICROSCOPY;

CELLULOSE; KETONE; NANOCRYSTAL; PALLADIUM; WATER; NANOPARTICLE;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; ELECTRON MICROSCOPY; ENANTIOSELECTIVITY; HYDROGENATION; ROOM TEMPERATURE; SURFACE PROPERTY; TOMOGRAPHY; TRANSMISSION ELECTRON MICROSCOPY; CHEMISTRY; STEREOISOMERISM; ULTRASTRUCTURE;

CATALYSTS; CELLULOSE DERIVATIVES; HYDROGENATION; TRANSMISSION ELECTRON MICROSCOPY;

CATALYSIS; CELLULOSE; HYDROGENATION; KETONES; MICROSCOPY, ELECTRON, TRANSMISSION; NANOPARTICLES; PALLADIUM; STEREOISOMERISM;

EID: 84930226958     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b02034     Document Type: Article

References (57)

1. Habibi, Y.; Lucia, L. A.; Rojas, O. J. Chem. Rev. 2010, 110, 3479
2. Thakur, V. K.; Thakur, M. K.; Raghavan, P.; Kessler, M. R. ACS Sust. Chem. Eng. 2014, 2, 1072
3. Rak, M. J.; Friscic, T.; Moores, A. Faraday Discuss. 2014, 170, 155
4. Moon, R. J.; Martini, A.; Nairn, J.; Simonsen, J.; Youngblood, J. Chem. Soc. Rev. 2011, 40, 3941
5. Klemm, D.; Kramer, F.; Moritz, S.; Lindström, T.; Ankerfors, M.; Gray, D.; Dorris, A. Angew. Chem., Int. Ed. 2011, 50, 5438
6. Ramires, E. C.; Dufresne, A. Tappi J. 2011, 10, 9
7. BelHaaj, S.; Ben Mabrouk, A.; Thielemans, W.; Boufi, S. Soft Matter 2013, 9, 1975
8. Liew, S. Y.; Thielemans, W.; Walsh, D. A. J. Phys. Chem. C 2010, 114, 17926
9. Liew, S. Y.; Walsh, D. A.; Thielemans, W. RSC Adv. 2013, 3, 9158
10. Kan, K. H. M.; Li, J.; Wijesekera, K.; Cranston, E. D. Biomacromolecules 2013, 14, 3130
11. Yang, J.; Han, C.-R.; Duan, J.-F.; Ma, M.-G.; Zhang, X.-M.; Xu, F.; Sun, R.-C.; Xie, X.-M. J. Mater. Chem. 2012, 22, 22467
12. Yang, X.; Cranston, E. D. Chem. Mater. 2014, 26, 6016
13. Querejeta-Fernández, A.; Chauve, G.; Methot, M.; Bouchard, J.; Kumacheva, E. J. Am. Chem. Soc. 2014, 136, 4788
14. Serizawa, T.; Sawada, T.; Wada, M. Chem. Commun. 2013, 49, 8827
15. Shopsowitz, K. E.; Qi, H.; Hamad, W. Y.; MacLachlan, M. J. Nature 2010, 468, 422
16. Shopsowitz, K. E.; Hamad, W. Y.; MacLachlan, M. J. J. Am. Chem. Soc. 2011, 134, 867
17. Qi, H.; Shopsowitz, K. E.; Hamad, W. Y.; MacLachlan, M. J. J. Am. Chem. Soc. 2011, 133, 3728
18. Giese, M.; Blusch, L. K.; Khan, M. K.; MacLachlan, M. J. Angew. Chem., Int. Ed. 2015, 54, 2888
19. Khan, M. K.; Bsoul, A.; Walus, K.; Hamad, W. Y.; MacLachlan, M. J. Angew. Chem. 2015, 127, 4378
20. Holt, B. L.; Stoyanov, S. D.; Pelan, E.; Paunov, V. N. J. Mater. Chem. 2010, 20, 10058
21. Lin, N.; Huang, J.; Dufresne, A. Nanoscale 2012, 4, 3274
22. Majoinen, J.; Haataja, J. S.; Appelhans, D.; Lederer, A.; Olszewska, A.; Seitsonen, J.; Aseyev, V.; Kontturi, E.; Rosilo, H.; Österberg, M.; Houbenov, N.; Ikkala, O. J. Am. Chem. Soc. 2013, 136, 866
23. Ding, K.; Uozumi, Y. Handbook of asymmetric heterogeneous catalysis; Wiley VCH: Weinheim, 2008.
24. Dalko, P. I. Enantioselective organocatalysis; Wiley VCH: Weinheim, 2007.
25. Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974
26. Cole-Hamilton, D. J. Science 2003, 299, 1702
27. Catalyst separation, recovery and recycling: chemistry and process design; Cole-Hamilton, D. J.; Tooze, R. P., Eds.; Springer: The Netherlands, 2006; Vol. 30.
28. Pélisson, C.-H.; Denicourt-Nowicki, A.; Meriadec, C.; Greneche, J.-M.; Roucoux, A. ChemCatChem 2014, 7, 309
29. Astruc, D.; Lu, F.; Aranzaes, J. R. Angew. Chem., Int. Ed. 2005, 44, 7852
30. Polshettiwar, V.; Varma, R. S. Green Chem. 2010, 12, 743
31. Polshettiwar, V.; Luque, R.; Fihri, A.; Zhu, H.; Bouhrara, M.; Basset, J.-M. Chem. Rev. 2011, 111, 3036
32. Wang, D.; Astruc, D. Chem. Rev. 2014, 114, 6949
33. Astruc, D. Nanoparticles and Catalysis; Wiley-VCH: Weinheim, 2008.
34. Song, C. E.; Sang-gi, L. Chem. Rev. 2002, 102, 3495-3524
35. Baiker, A. J. Mol. Catal. A: Chem. 1997, 115, 473
36. Heitbaum, M.; Glorius, F.; Escher, I. Angew. Chem., Int. Ed. 2006, 45, 4732
37. Demers-Carpentier, V.; Goubert, G.; Masini, F.; Lafleur-Lambert, R.; Dong, Y.; Lavoie, S.; Mahieu, G.; Boukouvalas, J.; Gao, H. L.; Rasmussen, A. M. H.; Ferrighi, L.; Pan, Y. X.; Hammer, B.; McBreen, P. H. Science 2011, 334, 776
38. Kyriakou, G.; Beaumont, S. K.; Lambert, R. M. Langmuir 2011, 27, 9687
39. Akabori, S.; Sakurai, S.; Izumi, Y.; Fujii, Y. Nature 1956, 178, 323
40. Beamer, R. L.; Fickling, C. S.; Ewing, J. H. J. Pharm. Sci. 1967, 56, 1029
41. Schwab, G.-M.; Rudolph, L. Naturwissenschaften 1932, 20, 363
42. Harada, K.; Yoshida, T. Naturwissenschaften 1970, 57, 131
43. Mallat, T.; E, O.; A, B. Chem. Rev. 2007, 107, 4863
44. Revol, J.-F.; Godbout, L.; Dong, X.-M.; Gray, D. G.; Chanzy, H.; Maret, G. Liq. Cryst. 1994, 16, 127
45. Picard, G.; Simon, D.; Kadiri, Y.; LeBreux, J.; Ghozayel, F. Langmuir 2012, 28, 14799
46. Cranston, E. D.; Gray, D. G. Biomacromolecules 2006, 7, 2522
47. Lam, E.; Male, K. B.; Chong, J. H.; Leung, A. C. W.; Luong, J. H. T. Trends Biotechnol. 2012, 30, 283
48. Cirtiu, C. M.; Dunlop-Brière, A. F.; Moores, A. Green Chem. 2011, 13, 288
49. Rezayat, M.; Blundell, R. K.; Camp, J. E.; Walsh, D. A.; Thielemans, W. ACS Sust. Chem. Eng. 2014, 2, 1241
50. Zhou, P.; Wang, H.; Yang, J.; Tang, J.; Sun, D.; Tang, W. Ind. Eng. Chem. Res. 2012, 51, 5743
51. Wu, X.; Lu, C.; Zhang, W.; Yuan, G.; Xiong, R.; Zhang, X. J. Mater. Chem. A 2013, 1, 8645
52. Lam, E.; Hrapovic, S.; Majid, E.; Chong, J. H.; Luong, J. H. T. Nanoscale 2012, 4, 997
53. Xiong, R.; Lu, C.; Zhang, W.; Zhou, Z.; Zhang, X. Carbohydr. Polym. 2013, 95, 214
54. Luska, K. L.; Moores, A. Adv. Synth. Catal. 2011, 353, 3167
55. Hou, Z.; Theyssen, N.; Brinkmann, A.; Leitner, W. Angew. Chem. 2005, 117, 1370
56. Cirtiu, C. M.; Hassani, H. O.; Bouchard, N.-A.; Rowntree, P. A.; Ménard, H. Langmuir 2006, 22, 6414
57. Andreiadis, E. S.; Vitale, M. R.; Mézailles, N.; Le Goff, X.; Le Floch, P.; Toullec, P. Y.; Michelet, V. Dalton Trans. 2010, 39, 10608