Synthesis and evaluation of molecular rotors with large and bulky tert-butyldiphenylsilyloxy-substituted trityl stators

Journal of Organic Chemistry

Volumn 77, Issue 16, 2012, Pages 6887-6894

  Arcos Ramos, Rafael ^a   Rodríguez Molina, Braulio ^b   Romero, Margarita ^a   Méndez Stivalet, J Manuel ^a   Ochoa, María Eugenia ^c   Ramírez Montes, Pedro I ^c   Santillan, Rosa ^c   Garcia Garibay, Miguel A ^b   Farfán, Norberto ^a  

^a Universidad Nacional Autonoma de Mexico Facultad de Quimica   (Mexico)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c DEPARTAMENTO DE FÍSICA   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTALLINITIES; ISOTOPOLOGUES; MOLECULAR ROTORS; ROTATIONAL DYNAMICS; SILYL GROUP; SOLID STATE CHARACTERIZATION; SOLID-STATE LED;

STATORS;

ROTORS (WINDINGS);

1,4 BIS [3,3 BIS [3 (TERT BUTYLDIPHENYLSILANYLOXY) PHENYL]3 PHENYLPROPYNYL]PHENYLENE; 1,4 BIS [[[3 (TERT BUTYLDIPHENYLSILANYLOXY) DIPHENYL]PHENYLMETHYL]ETHYNYL]PHENYLENE; 1,4 BIS [[TRIS [3 (TERT BUTYLDIPHENYLSILANYLOXY) PHENYL]METHANYL]ETHYNYL]PHENYLENE; 1,4 DIETHYNYLPHENYLENE; DIAMINE; UNCLASSIFIED DRUG;

ARTICLE; CALORIMETRY; CRYSTAL STRUCTURE; CRYSTALLIZATION; DEUTERON NUCLEAR MAGNETIC RESONANCE; SOLID; SUBSTITUTION REACTION; SYNTHESIS; THERMOSTABILITY; X RAY ANALYSIS;

EID: 84865270300     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301078a     Document Type: Article

References (36)

1. Prokop, A.; Vacek, J.; Michl, J. ACS Nano 2012, 6, 1901-1914
2. Rodríguez-Velamazán, J. A.; González, M. A.; Real, J. A.; Castro, M.; Muñoz, M. C.; Gaspar, A. B.; Ohtani, R.; Ohba, M.; Yoneda, K.; Hijikata, Y.; Yanai, N.; Mizuno, M.; Ando, H.; Kitagawa, S. J. Am. Chem. Soc. 2012, 134, 5083-5089
3. Coskun, A.; Banaszak, M.; Astumian, R. D.; Stoddart, J. F.; Grzybowski, B. A. Chem. Soc. Rev. 2012, 41, 19-30
4. Garcia-Garibay, M. A. Nat. Mater. 2008, 7, 431-432
5. Garcia-Garibay, M. A. Angew. Chem., Int. Ed. 2007, 46, 8945-8947
6. Kottas, G. S.; Clarke, L. I.; Horinek, D.; Michl, J. Chem. Rev. 2005, 105, 1281-1376
7. Vogelsberg, C. S.; Garcia-Garibay, M. A. Chem. Soc. Rev. 2012, 41, 1892-1910
8. Khuong, T.-A. V.; Nuñez, J. E.; Godinez, C. E.; Garcia-Garibay, M. A. Acc. Chem. Res. 2006, 39, 413-422
9. Garcia-Garibay, M. A. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 10793
10. Akutagawa, T.; Nakamura, T. Dalton Trans. 2008, 6335
11. Akutagawa, T.; Koshinaka, H.; Sato, D.; Takeda, S.; Noro, S.-I.; Takahashi, H.; Kumai, R.; Tokura, Y.; Nakamura, T. Nat. Mater. 2009, 8, 342
12. Setaka, W.; Ohmizu, S.; Kira, M. Chem. Lett. 2010, 39, 468469
13. Winston, B.; Lowell, P. J.; Vacek, J.; Chocholoušová, J.; Michl, J.; Price, J. C. Phys. Chem. Chem. Phys. 2008, 10, 5188
14. Bracco, S.; Comotti, A.; Valsesia, P.; Chmelka, B. F.; Sozzani, P. Chem. Commun. 2008, 4798
15. 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, 14973-14977
16. Karlen, S. D.; Ortiz, R.; Chapman, O. L.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 2005, 127, 6554-6555
17. Akimov, A. V.; Kolomeisky, A. B. J. Phys. Chem. C 2011, 115, 13584-13591
18. Jarowski, P. D.; Houk, K. N.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 2007, 129, 3110-3117
19. Godinez, C. E.; Garcia-Garibay, M. A. Cryst. Growth Des. 2009, 9, 3124-3128
20. Domínguez, Z.; Dang, H.; Strouse, J. M.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 2002, 124, 7719-7727
21. Commins, P.; Nuñez, J. E.; Garcia-Garibay, M. A. J. Org. Chem. 2011, 73, 8355-8363
22. Rodríguez-Molina, B.; Farfán, N.; Romero, M.; Mendez-Stivalet, J. M.; Santillan, R.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 2011, 133, 7280-7283
23. Rodríguez-Molina, B.; Pozos, A.; Cruz, R.; Romero, M.; Flores, B.; Farfán, N.; Santillan, R.; Garcia-Garibay, M. A. Org. Biomol. Chem. 2010, 8, 2993-3000
24. Gould, S. L.; Tranchemontagne, D.; Yaghi, O. M.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 2008, 130, 3246-3247
25. Namba, K.; Vonderviszt, F. Q. Rev. Biophys. 1997, 30, 1
26. Yoshida, M.; Muneyuki, E.; Hisabori, T. Nat. Rev. 2001, 2, 669
27. O'Brien, Z. J.; Natarajan, A.; Khan, S. I.; Garcia-Garibay, M. A. Cryst. Growth Des. 2011, 11, 2654-2659
28. Kocienski, P. In Protecting Groups, 3 rd ed; Thieme: Stuttgart, 2003.
29. Hiroshi, S.; Tashiro, K.; Shinmori, H.; Osuka, A.; Aida, T. Chem. Commun. 2005, 2324-2326
30. Lulinski, P.; Skulski, L. Bull. Chem. Soc. Jpn. 2000, 73, 951-956
31. Scudder, M; Dance, I. J. Chem. Soc., Dalton Trans. 2000, 1, 2909-2915
32. Malone, J. F.; Murray, C. M.; Charlton, M. H.; Docherty, R.; Lavery, A. J. J. Chem. Soc., Faraday Trans. 1997, 93, 3429-3436
33. Macrae, C. F.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Shields, G. P.; Taylor, R.; Towler, M.; van de Streek, J. J. Appl. Crystallogr. 2006, 39, 453-457
34. Ratcliffe, C. I. Rotational & Translational Dynamics. In NMR Crystallography; Harris, R. K.; Wasylishen, R. E.; Duer, M. J., Eds.; Wiley: Hoboken, NJ, 2009.
35. Macho, V.; Brombacher, L.; Spiess, H. W. Appl. Magn. Reson. 2001, 405
36. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837-838