Inclusion compound based approach to arrays of artificial dipolar molecular rotors. A surface inclusion

Journal of the American Chemical Society

Volumn 134, Issue 24, 2012, Pages 10122-10131

  Kobr, Lukáš ^a   Zhao, Ke ^a   Shen, Yongqiang ^a   Comotti, Angiolina ^b   Bracco, Silvia ^b   Shoemaker, Richard K ^a   Sozzani, Piero ^b   Clark, Noel A ^a   Price, John C ^a   Rogers, Charles T ^a   Michl, Josef ^a,c  

^a UNIVERSITY OF COLORADO   (United States)

^b UNIVERSITY OF MILANO BICOCCA   (Italy)

^c INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

INCLUSION COMPOUNDS; MOLECULAR ROTORS; POWDER X RAY DIFFRACTION; ROTATIONAL BARRIERS; SOLID STATE NMR; SURFACE INCLUSION; TRIANGULAR ARRAYS; TRIS(O-PHENYLENEDIOXY)CYCLOTRIPHOSPHAZENE;

DIFFERENTIAL SCANNING CALORIMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

X RAY DIFFRACTION;

1 HEXADECYL 12 (2,3 DICHLOROPHENYL) 4 DICARBA CLOSO DODECABORANE; CHEMICAL COMPOUND; TRIS(2 PHENYLENEDIOXY)CYCLOTRIPHOSPHAZENE; UNCLASSIFIED DRUG;

ARTICLE; ARTIFICIAL DIPOLAR MOLECULAR ROTOR; DIFFERENTIAL SCANNING CALORIMETRY; ELECTROCHEMICAL IMPEDANCE SPECTROSCOPY; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ROTATION; SYNTHESIS; X RAY DIFFRACTION;

EID: 84862571273     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja302173y     Document Type: Article

References (61)

1. Kottas, G. S.; Clarke, L. I.; Horinek, D.; Michl, J. Chem. Rev. 2005, 105, 1281
2. Khuong, T.-A. V.; Nunez, J. E.; Godinez, C. E.; Garcia-Garibay, M. A. Acc. Chem. Res. 2006, 39, 413
3. Horansky, R. D.; Magnera, T. F.; Price, J. C.; Michl, J. In Controlled Nanoscale Motion; Lecture Notes in Physics, Vol. 711; Linke, H.; Månsson, A., Eds.; Springer: Berlin and Heidelberg, 2007; p 303.
4. Crowly, J. D.; Kay, E. R.; Leigh, D. A. Intell. Mater. 2008, 1
5. Garcia-Garibay, M. A. Nat. Mater. 2008, 7, 431
6. Michl, J.; Sykes, E. C. H. ACS Nano 2009, 3, 1042
7. Augulis, R.; Klok, M.; Feringa, B. L. Phys. Status Solidi C 2009, 6, 181
8. Dominiguez, Z.; Dang, H.; Strouse, M. J.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 2002, 124, 2398
9. Rodriguez-Molina, B.; Ochoa, M. E.; Farfan, N.; Santillan, R.; Garcia-Garibay, M. A. J. Org. Lett. 2009, 74, 8554
10. Karlen, S. D.; Reyes, H.; Taylor, R. E.; Khan, S. I.; Hawthorne, M. F.; Garcia-Garibay, M. A. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 14973
11. Winston, E. B.; Lowell, P. J.; Vacek, J.; Chocholoušová, J.; Michl, J.; Price, J. C. Phys. Chem. Chem. Phys. 2008, 10, 5188
12. Gould, S. L.; Tranchemontagne, D.; Yaghi, O. M.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 2008, 130, 3246
13. Lemouchi, C.; Vogelsberg, C. S.; Zorina, L.; Simonov, S.; Batail, P.; Brown, S.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 2011, 133, 6371
14. Gimzewski, J. K.; Joachhim, C.; Schlitter, R. R.; Langlias, V.; Tang, H.; Johannsen, I. Science 1998, 281, 531
15. Stipe, B. C.; Rezaei, M. A.; Ho, W. Science 1998, 279, 1907
16. Rao, B. V.; Kwon, K.-Y.; Liu, A.; Bartels, L. J. Chem. Phys. 2003, 119, 10879
17. Sainoo, Y.; Kim, Y.; Komeda, T.; Kawai, M.; Shigekawa, H. Surf. Sci. 2003, 536, L403
18. Delden, R. A.; ter Wiel, M. K. J.; Pollard, M. M.; Vicario, J.; Koumura, N.; Feringa, B. L. Nature 2005, 437, 1337
19. Tierney, H. L.; Murphy, C. J.; Jewell, A. D.; Baber, A. E.; Iski, E. V.; Khodaverdian, H. Y.; McGuire, A. F.; Klebanov, N.; Sykes, E. C. H. Nature Nanotechnol. 2011, 6, 625
20. Zheng, X.; Mulcahy, M. E.; Horinek, D.; Galeotti, F.; Magnera, T. F.; Michl, J. J. Am. Chem. Soc. 2004, 126, 4540
21. Clarke, L. I.; Horinek, D.; Kottas, G. S.; Varaksa, N.; Magnera, T. F.; Hinderer, T. P.; Horansky, R. D.; Michl, J.; Price, J. C. Nanotechnology 2002, 13, 533
22. Eelkema, R.; Pollard, M. M.; Vicario, J.; Katsonis, N.; Ramon, B. S.; Bastiaansen, C. W. M.; Broer, D. J.; Feringa, B. L. Nature 2006, 440, 163
23. Pollard, M. M.; Lubomska, M.; Rudolf, P.; Feringa, B. L. Angew. Chem., Int. Ed. 2007, 46, 1278
24. Carroll, G. T.; Pollard, M. M.; van Delden, R.; Feringa, B. L. Chem. Sci. 2010, 1, 97
25. OBrien, Z. J.; Karlen, S. D.; Khan, S.; Garcia-Garibay, M. A. J. Org. Chem. 2010, 75, 2482
26. Rodriguez-Molina, B.; Farfan, N.; Romero, M.; Mendez-Stivalet, J. M.; Santillan, R.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 2011, 133, 7280
27. Mulcahy, M. E.; Magnera, T. F.; Michl, J. J. Phys. Chem. C 2009, 113, 20698
28. Horansky, R. D.; Clarke, L. I.; Winston, E. B.; Price, J. C.; Karlen, S. D.; Jarowski, P. D.; Santillan, R.; Garcia-Garibay, M. A. Phys. Rev. B 2006, 74, 054306
29. Rozenbaum, V. M.; Ogenko, V. M.; Chuiko, A. A. Phys.-Usp. 1991, 34, 883
30. Allcock, H. R.; Siegel, L. A. J. Am. Chem. Soc. 1964, 86, 5140
31. Sozzani, P.; Comotti, A.; Simonutti, R.; Meersmann, T.; Logan, J. W.; Pines, A. Angew. Chem., Int. Ed. 2000, 39, 2695
32. Sozzani, P.; Bracco, S.; Comotti, A.; Ferretti, L.; Simonutti, R. Angew. Chem., Int. Ed. 2005, 44, 1816
33. Meersmann, T.; Logan, J. W.; Simonutti, R.; Caldarelli, S.; Sozzani, P.; Comotti, A.; Kaiser, L.; Pines, A. J. Phys. Chem. A 2000, 104, 11665
34. Meitrovitch, E.; Belsky, I.; Vega, S. J. Phys. Chem. 1984, 88, 1522
35. Allcock, H. R.; Levin, M. L.; Whittle, R. R. Inorg. Chem. 1986, 25, 41
36. Primrose, A. P.; Parvez, M.; Allcock, H. R. Macromolecules 1997, 30, 670
37. Comotti, A.; Simonutti, R.; Catel, G.; Sozzani, P. Chem. Mater. 1999, 11, 1476
38. Comotti, A.; Simonutti, R.; Stramare, S.; Sozzani, P. Nanotechnology 1999, 10, 70
39. Brustolon, M.; Barbon, A.; Bortolus, M.; Maniero, A. L.; Sozzani, P.; Comotti, A.; Simonutti, R. J. Am. Chem. Soc. 2004, 126, 15512
40. Sozzani, P.; Comotti, A.; Bracco, S.; Simonutti, R. Chem. Commun. 2004, 768
41. Sozzani, P.; Comotti, A.; Bracco, S.; Simonutti, R. Angew. Chem., Int. Ed. 2004, 43, 2792
42. Bracco, S.; Comotti, A.; Valsesia, P.; Beretta, M.; Sozzani, P. Cryst. Eng. Commun. 2010, 12, 2318
43. Bracco, S.; Comotti, A.; Ferretti, L.; Sozzani, P. J. Am. Chem. Soc. 2011, 133, 8982
44. Herzog, A.; Knobler, C. B.; Hawthorne, M. F.; Maderna, A.; Siebert, W. J. Org. Chem. 1999, 64, 1045
45. Ito, N.; Esaki, H.; Maesawa, T.; Imamiya, E.; Maegawa, T.; Sajiki, H. Bull. Chem. Soc. Jpn. 2008, 81, 278
46. Allcock, H. R. J. Am. Chem. Soc. 1963, 85, 4050
47. Tonelli, A. NMR Spectroscopy and Polymer Microstructure: The Conformational Connection; VCH Publishers: Deerfeld Beach, 1988.
48. Comotti, A.; Bracco, S.; Ferretti, L.; Mauri, M.; Simonutti, R.; Sozzani, P. Chem. Commun. 2007, 350
49. Vinogradov, E.; Madhu, P. K.; Vega, S. Chem. Phys. Lett. 1999, 314, 443
50. Sozzani, P.; Bracco, S.; Comotti, A.; Simonutti, R.; Camurati, I. J. Am. Chem. Soc. 2003, 125, 12881
51. Hurdis, E. C.; Smyth, C. P. J. Am. Chem. Soc. 1942, 64, 2212
52. Becker, P.; Comotti, A.; Simonutti, R.; Sozzani, P.; Saalwachter, K. J. Phys. Chem. B 2005, 109, 23285
53. Sozzani, P.; Bracco, S.; Comotti, A.; Simonutti, R. Adv. Polym. Sci. 2005, 181, 153
54. Bondi, A. J. Phys. Chem. 1964, 68, 441
55. Allcock, H. R.; Allen, R. W.; Bissell, E. C.; Smeltz, L. A.; Teeter, M. J. Am. Chem. Soc. 1976, 98, 5120
56. Schwab, P. F. H.; Levin, M. D.; Michl, J. Chem. Rev. 1999, 99, 1863
57. Bohn, R. K.; Bohn, M. D. Inorg. Chem. 1971, 10, 350
58. Masao, O.; Mariko, U.; Masahiko, A.; Junko, Y.; Ichiro, Y. J. Mol. Struct. 1986, 147, 77
59. Schöberl, U.; Magnera, T. F.; Harrison, R.; Fleischer, F.; Pflug, J. L.; Schwab, P. F. H.; Meng, X.; Lipiak, D.; Noll, B. C.; Allured, V. S.; Rudalevige, T.; Lee, S.; Michl, J. J. Am. Chem. Soc. 1997, 119, 3907
60. Sozzani, P.; Bovey, F. A.; Schilling, F. C. Macromolecules 1991, 24, 6764
61. Meitrovitch, E. J. Phys. Chem. 1984, 88, 6411