Size dependence of nanoscale confinement on chiral transformation

Chemistry - A European Journal

Volumn 16, Issue 22, 2010, Pages 6482-6487

  Wang, Zhigang ^a,b,c   Wang, Chunlei ^a,d   Xiu, Peng ^a   Qi, Wenpeng ^a   Tu, Yusong ^a   Shen, Yumei ^a   Zhou, Ruhong ^e,f   Zhang, Ruiqin ^b   Fang, Haiping ^a  

^a SHANGHAI INSTITUTE OF APPLIED PHYSICS   (China)

^b CITY UNIVERSITY OF HONG KONG   (Hong Kong)

^c JILIN UNIVERSITY   (China)

^d UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

^e IBM T J WATSON RESEARCH CENTER   (United States)

^f NONE   (United States)

Author keywords

Arenes; Chiral transitions; Fluorine; Molecular dynamics nanostructures

Indexed keywords

ARENES; BORON-NITRIDE NANOTUBES; CHIRAL TRANSITION; CHIRAL TRANSITIONS; CRITICAL TEMPERATURES; INTERACTION ENERGIES; MOLECULAR CHIRALITY; MOLECULAR DYNAMIC SIMULATIONS; NANOSCALE CONFINEMENT; NANOTUBE DIAMETERS; SINGLE-WALLED; SIZE DEPENDENCE; TEMPERATURE THRESHOLDS;

AROMATIC COMPOUNDS; BORON; BORON NITRIDE; COMPUTER SIMULATION; FLUORINE; MOLECULAR DYNAMICS; MOLECULES; NANOSTRUCTURED MATERIALS; NANOTUBES; NITRIDES; STEREOCHEMISTRY;

ORGANIC POLYMERS;

DIFLUOROBENZO(C)PHENANTHRENE; FLUORINE; NANOTUBE; PHENANTHRENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; NANOTECHNOLOGY; QUANTUM THEORY; STEREOISOMERISM; TEMPERATURE; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; FLUORINE; MODELS, MOLECULAR; NANOTECHNOLOGY; NANOTUBES; PHENANTHRENES; QUANTUM THEORY; STEREOISOMERISM; TEMPERATURE; THERMODYNAMICS;

EID: 77953174117     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200903383     Document Type: Article

References (55)

1. R. A. Sheldon, Chirotechnology, Dekker, New York, 1993.
2. D. B. Cline, Physical Origin of Homochirality in Life, AIP, Woodbury, 1996.
3. G. Blaschke, H. P. Kraft, H. Markgraf, Chem. Ber. 1980, 113, 2318.
4. T. Eriksson, S. Björkman, B. Roth, A. Fyge, P. Höglund, Chirality 1998, 10, 223.
5. J. Caldwell, Chem. Ind. 1995, 5, 176.
6. M. Inouye, M. Waki, H. Abe, J. Am. Chem. Soc. 2004, 126, 2022.
7. M. Waki, H. Abe, M. Inouye, Angew. Chem. 2007, 119, 3119;
8. Angew. Chem. Int. Ed. 2007, 46, 3059.
9. H. Abe, H. Machiguchi, S. Matsumoto, M. Inouye, J. Org. Chem. 2008, 73, 4650.
10. S. H. Wilen, J. Z. Qi, P. G. Williard, J. Org. Chem. 1991, 56, 485.
11. J. F. Larrow, E. N. Jacobsen, Y. Gao, Y. P. Hong, X. Y. Nie, C. M. Zepp, J. Org. Chem. 1994, 59, 1939.
12. P. J. Harrington, E. Lodewijk, Org. Process Res. Dev. 1997, 1, 72.
13. M. Periasamy, Aldrichimica Acta 2002, 35, 89.
14. T. Brotin, R. Barbe, M. Darzac, J.-P. Dutasta, Chem. Eur. J. 2003, 9, 5784.
15. J. Schindler, M. Egressy, X Bálint, Z. Hell, E. Fogassy, Chirality 2005, 17, 565.
16. K. Sakai, R. Sakurai, N. Hirayama, Top. Curr. Chem. 2006, 269, 233.
17. H. Umeda, M. Takagi, S. Yamada, S. Koseki, Y. Fujimura, J. Am. Chem. Soc. 2002, 124, 9265.
18. N. P. M. Huck, W. F. Jager, B. de Lange, B. L. Feringa, Science 1996, 273, 1686.
19. T. Vries, H. Wynberg, E. van Echten, J. Koek, W. ten Hoeve, R. M. Kellogg, Q. B. Broxterman, A. Minnaard, B. Kaptein, S. van der Sluis, L. Hulshof, J. Kooistra, Angew. Chem. 1998, 110, 2491;
20. Angew. Chem. Int. Ed. 1998, 37, 2349.
21. "Optical Resolution by Inclusion Complexation with a Chiral Host Compound": Enantiomer Separation: Fundamentals and Practical Methods (Ed.: E Toda), Kluwer Academic, New York, 2004.
22. B. L. Feringa, R. A. van Delden, N. Koumura, E. M. Geertsema, Chem. Rev. 2000, 100, 1789.
23. G. A. Hembury, V. V. Borovkov, Y. Inoue, Chem. Rev. 2008, 108, 1.
24. M. S. Strano, J. Am. Chem. Soc. 2003, 125, 16148.
25. G. Dukovic, M. Balaz, P. Doak, N. D. Berova, M. Zheng, R. S. McLean, L. E. Brus, J. Am. Chem. Soc. 2006, 128, 9004.
26. X. Peng, N. Komatsu, S. Bhattacharya, T. Shimawaki, S. Aonuma, T. Kimura, A. Osuka, Nat. Nanotechnol. 2007, 2, 361.
27. Q. Chenand, N. V. Richardson, Nat. Mater. 2003, 2, 324.
28. A. Kühnle, T. R. Linderoth, B. Hammer, F. Besenbacher, Nature 2002, 415, 891.
29. J. A. Switzer, H. M. Kothari, P. Poizot, S. Nakanishi, E. W. Bohannan, Nature 2003, 425, 490.
30. C. A. Orme, A. Noy, A. Wierzbicki, M. T. McBride, M. Grantham, H. H. Teng, P. M. Dove, J. J. DeYoreo, Nature 2001, 411, 775.
31. J. W. Kim, M. Carbone, J. H. Dil, M. Tallarida, R. Flammini, M. P. Casaletto, K. Horn, M. N. Piancastelli, Phys. Rev. Lett. 2005, 95, 107601.
32. S. Blankenburg, W. G. Schmidt, Phys. Rev. Lett 2007, 99, 196107.
33. R. B. Rankin, D. S. Sholl, J. Chem. Phys. 2006, 124, 074703.
34. C. Girardet, D. Vardanega, F. Picaud, Chem. Phys. Lett. 2007, 443, 113.
35. X. L. Pan, Z. L. Fan, W. Chen, Y. X. Ding, H. Y. Luo, X. H. Bao, Nat Mater. 2007, 6, 507.
36. H. Q. Yang, L. Zhang, L. Zhong, Q. H. Yang, C. Li, Angew. Chem. 2007, 119, 6985;
37. Angew. Chem. Int. Ed. 2007, 46, 6861.
38. B. Y. Wang, P. Kra, I. Thanopulos, Nano Lett. 2006, 6, 1918.
39. D. K. Eggers, J. S. Valentine, Protein Sci. 2001, 10, 250.
40. D. Lucent, V. Vishal, V. S. Pande, Proc. Natl. Acad. Sci. USA 2007, 104, 10430.
41. W. X. Xu, J. Wang, W. Wang, Proteins 2005, 61, 777.
42. H. J. Gao, Y. Kong, D. X. Cui, C. S. Ozkan, Nano Lett. 2003, 3, 471.
43. R. H. Zhou, X. H. Huang, C. J. Margulis, B. J. Berne, Science 2004, 305, 1605.
44. S. Q. Zhang, M. S. Cheung, Nano Lett. 2007, 7, 3438.
45. A. Cacciuto, E. Luijten, Nano Lett. 2006, 6, 901.
46. C. Y. Bao, Q. Gan, B. Kauffmann, H. Jiang, I. Huc, Chem. Eur. J. 2009, 15, 11530.
47. R. Z. Wan, J. Y. Li, H. J. Lu, H. P. Fang, J. Am. Chem. Soc. 2005, 127, 7166.
48. J. Y. Li, X. J. Gong, H. J. Lu, D. Li, H. P. Fang, R. H. Zhou, Proc. Natl. Acad. Sci. USA 2007, 104, 3687.
49. X. J. Gong, J. Y. Li, H. J. Lu, R. Z. Wan, J. C. Li, J. Hu, H. P. Fang, Nat. Nanotechnol. 2007, 2, 709.
50. D. Golberg, Y. Bando, C. C. Tang, C. Y. Zhi, Adv. Mater. 2007, 19, 2413.
51. M. J. S. Dewar, E. G. Zoebisch, E. E Healy, J. Am. Chem. Soc. 1985, 107, 3902.
52. Gaussian 03, Revision D.01, M.J. Frisch, G.W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, C. Adamo, J. Maramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pole, Gaussian Inc., Wallingford CT, 2004.
53. D. van der Spoel, E. Lindahl, B. Hess, G. Groenhof, A. E. Mark, H. J. C. Berendsen, J. Comput. Chem. 2005, 26, 1701.
54. "A Guide to Monte Carlo for Statistical Mechanics: 2. Byways": J. P. Valleau, G. M. Torrie in Statistical Mechanics. Part A: Equilibrium Techniques, Vol. 5 (Ed.: B. J. Berne), Plenum, New York, 1977.
55. S. Kumar, D. Bouzida, R. H. Swendsen, P. A. Kollman, J. M. Rosenberg, J. Comput. Chem. 1992, 13, 1011.