Photochemical and thermal behavior of light-driven unidirectional molecular motor with long alkyl chains

Tetrahedron

Volumn 64, Issue 25, 2008, Pages 5956-5962

  Caroli, Giuseppe ^a   Kwit, Marcin G ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; HYDROCARBON;

ARTICLE; ISOMERIZATION; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE; PHOTOCHEMISTRY; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS; THERMAL ANALYSIS;

EID: 43449111477     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.03.098     Document Type: Article

References (65)

1. In: Schliwa M. (Ed). Molecular Motors (2003), Wiley-VCH, Weinheim
2. Boyer P.D. Angew. Chem., Int. Ed. 37 (1998) 2296-2307
3. Walker J.E. Angew. Chem., Int. Ed. 37 (1998) 2308-2319
4. Vale R.D., and Milligan R.A. Science 288 (2000) 88-95
5. In: Feringa B.L. (Ed). Molecular Switches (2001), Wiley-VCH, Weinheim
6. In: Sauvage J.P., and Dietrich-Buchecker C. (Eds). Molecular Catenanes, Rotaxane and Knots (1999), Wiley-VCH, Weinheim
7. Balzani V., Gomez-Lopez M., and Stoddart J.F. Acc. Chem. Res. 31 (1998) 405-414
8. In: Stoddart J.F. (Ed). Molecular machines, Special Issue. Acc. Chem. Res. 34 (2001) 410-411
9. Iwamura H., and Mislow K. Acc. Chem. Res. 21 (1988) 175-182
10. In: Irie M. (Ed). Photochroism: memories and switches, Special Issue. Chem. Rev. 100 (2000) 1683-1684
11. Kelly T.R., Bowyer M.C., Bhaskar K.V., Bebbington D., Garcia A., Lang F., Kim M.H., and Jette M.P. J. Am. Chem. Soc. 116 (1994) 3657-3658
12. Bedard T.C., and Moore J.S. J. Am. Chem. Soc. 117 (1995) 10662-10671
13. Ashton P., Baldoni V.R., Balzani V., Credi A., Hoffman H.D.A., Martinez-Diaz M.V., Raymo F.M., Stoddart J.F., and Venturi M. Chem.-Eur. J. 7 (2001) 3482-3493
14. Pease A.R., Jeppesen J.O., Stoddart J.F., Luo Y., Collier C.P., and Heath J.R. Acc. Chem. Res. 34 (2001) 433-444
15. Ballardini R., Balzani V., Credi A., Gandolfi M.T., and Venturi M. Acc. Chem. Res. 34 (2001) 445-455
16. Brower A.M., Frochot T., Gatti F.G., Leigh D.A., Mottier L., Paolucci F., Roffia S., and Wurpel G.W.H. Science 291 (2001) 2124-2128
17. Jimenez-Molero M.C., Dietrich-Buchecker C., and Sauvage J.-P. Chem.-Eur. J. 8 (2002) 1456-1465
18. Bottari G., Leigh D.A., and Perez E.M. J. Am. Chem. Soc. 125 (2003) 13360-13361
19. Da Ros T., Guldi D.M., Farran Morales A., Leigh D.A., Prato M., and Turco R. Org. Lett. 5 (2003) 689-691
20. Chang S.-Y., and Jeong K.-S. J. Org. Chem. 68 (2003) 4014-4019
21. Altieri A., Gatti F.G., Kay E.R., Leigh D.A., Martel D., Paolucci F., Slawin A.M.Z., and Wong J.K.Y. J. Am. Chem. Soc. 125 (2003) 8644-8654
22. Huang T.J., Tseng H.-R., Sha L., Lu V., Brough B., Flood A.H., Yu B.-D., Celestre P.C., Chang J.P., Stoddart J.F., and Ho C.-M. Nano Lett. 4 (2004) 2065-2071
23. Keaveney C.M., and Leigh D.A. Angew. Chem., Int. Ed. 43 (2004) 1222-1224
24. Steuermann D.W., Tseng H.-R., Peters A.J., Flood A.H., Jeppesen J.O., Nielsen K.A., Stoddart J.F., and Heath J.R. Angew. Chem., Int. Ed. 43 (2004) 6486-6491
25. Muraoka T., Kinbara K., Kobayashi Y., and Aida T. J. Am. Chem. Soc. 125 (2003) 5612-5613
26. Badjiæ J.D., Balzani V., Credi A., Silvi S., and Stoddart J.F. Science 303 (2004) 1845-1849
27. Tashiro K., Konishi K., and Aida T. J. Am. Chem. Soc. 122 (2000) 7921-7926
28. Jimenez M.C., Dietrich-Buchecker C., and Sauvage J.-P. Angew. Chem., Int. Ed. 39 (2000) 3284-3287
29. Schoevaars A.M., Kruizinga W., Zijlstra R.W.J., Veldman L., Spek A.L., and Feringa B.L. J. Org. Chem. 62 (1997) 4943-4948
30. Bermudez V., Capron N., Gase T., Gatti F.G., Kajzar F., Leigh D.A., Zerbetto F., and Zhang S. Nature 406 (2000) 608-610
31. Dominguez Z., Dang H., Strouse M.J., and Garcia-Garibay M.A. J. Am. Chem. Soc. 124 (2002) 2398-2399
32. Godlinez C.E., Zepada G., and Garcia-Garibay M.A. J. Am. Chem. Soc. 124 (2002) 7719-7727
33. Kuwatani Y., Yamamoto G., and Iyoda M. Org. Lett. 5 (2003) 3371-3374
34. Dominguez Z., Khuong T.-A.V., Dang H., Sanrame C.N., Nunez J.E., and Garcia-Garibay M.A. J. Am. Chem. Soc. 125 (2003) 8827-8837
35. Leigh D.A., Wong J.K.Y., Dehez F., and Zerbetto F. Nature 424 (2003) 174-178
36. Hawthorne M.F., Zink J.I., Skelton J.M., Bayer M.J., Liu C., Livshits E., Baer R., and Neuhauser D. Science 303 (2004) 1849-1851
37. Carella A., Rappenne G., and Launey J.-P. New J. Chem. 29 (2005) 288-290
38. For a comprehensive review, see:. Kottas G.S., Clarke L.I., Horinek D., and Michl J. Chem. Rev. 105 (2005) 1281-1376
39. Kelly T.R., Sestelo J.P., and Tellitu I. J. Org. Chem. 63 (1998) 3655-3665
40. Harrington L.E., Cahill L.S., and McGlinchey M.J. Organometallics 23 (2004) 2884-2891
41. Ismagilov R.F., Schwartz A., Bowden N., and Whitesides G.M. Angew. Chem., Int. Ed. 41 (2002) 652-654
42. Paxton W.F., Kisler K.C., Olmeda C.C., Sen A., St. Angelo S.K., Coa Y., Mallouk T.E., Lammert P.E., and Crespi V.H. J. Am. Chem. Soc. 126 (2004) 13424-13431
43. Catchmark J.M., Subramanian S., and Sen A. Small 1 (2005) 202-206
44. Kline T.R., Paxton W.F., Mallouk T.E., and Sen A. Angew. Chem., Int. Ed. 44 (2005) 744-746
45. Fournier-Bidoz S., Arsenault A.C., Manners I., and Ozin G.A. Chem. Commun. (2005) 441-443
46. Vicario J., Eelkema R., Browne W.R., Meetsma A., La Crois R.M., and Feringa B.L. Chem. Commun. (2005) 3936-3938
47. Credi A. Aust. J. Chem. (2006) 157-169
48. Browne W.R., and Feringa B.L. Nat. Nanotechnol. (2006) 25-35
49. Kay E.R., Leigh D.A., and Zerbetto F. Angew. Chem., Int. Ed (2006) 72-191
50. Saha S., and Stoddart J.F. Chem. Soc. Rev. (2007) 77-92
51. Kottas G.S., Clarke L.I., Horinek D., and Michl J. Chem. Rev. (2005) 1281-1376
52. Pollard M.M., Klok M., Pijper D., and Feringa B.L. Adv. Funct. Mater. 17 (2007) 718-729
53. Koumura N., Zijlstra R.W.J., van Delden R.A., Harada N., and Feringa B.L. Nature 401 (1999) 152-155
54. ter Wiel M.K.J., van Delden R.A., Meetsma A., and Feringa B.L. J. Am. Chem. Soc. 125 (2003) 15076-15086
55. Fujita T., Kuwahara S., and Harada N. Eur. J. Org. Chem. 21 (2005) 4533-4543
56. ter Wiel M.K.J., van Delden R.A., Meetsma A., and Feringa B.L. J. Am. Chem. Soc. 127 (2005) 14208-14222
57. Vicario J., Walko M., Meetsma A., and Feringa B.L. J. Am. Chem. Soc. 128 (2006) 5127-5135
58. The weight of the two chains is higher than the motor itself, albeit it is reasonable to envision that the remote part of the chains 'feels' the rotation of the motor much less than the alkyl moieties in proximity to the motor unit.
59. Harada N., Koumura N., and Feringa B.L. J. Am. Chem. Soc. 119 (1997) 7256-7264
60. Williams C.M., and Mander L.N. Tetrahedron (2001) 425-447
61. This prediction was also confirmed during the NMR experiments, where, although without a quantitative kinetic study by NMR, the two thermal inversions showed a clearly different rate.
62. For similar calculations, see: van Delden, R. A. Ph.D. Thesis, University of Groningen, 2002;
63. ter Wiel, M. K. J. Ph.D. Thesis, University of Groningen, 2004.
64. For some examples of the effect of bulky groups at the stereogenic centers, see Refs. 23 and 28b.
65. Ford W.T., and Pietsek D.J.J. J. Am. Chem. Soc. 97 (1975) 2198-2205