C - H⋯F hydrogen bonding: The origin of the self-assemblies of bis(2,2'-difluoro-1,3,2-dioxaborine)

Langmuir

Volumn 22, Issue 10, 2006, Pages 4750-4757

  Rohde, Dirk ^a   Yan, Cun Ji ^a,b   Wan, Li Jun ^a  

^a INSTITUTE OF CHEMISTRY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

HALOGEN COMPOUNDS; HYDROGEN BONDS; MOLECULAR DYNAMICS; ORGANIC COATINGS; SELF ASSEMBLY; SURFACE REACTIONS;

ELECTRON AFFINITIES; INTERMOLECULAR INTERACTIONS; ORTHO CARBON; PHENYL RING;

MONOLAYERS;

EID: 33744799009     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la053138+     Document Type: Article

References (70)

1. (a) Lenn, J. M. Science 2002, 295, 2400.
2. (b) Lehn, J. M. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4763.
3. (a) Whitesides, G. M.; Gryzybowski, B. Science 2002, 295, 2418-2421.
4. (b) Requicha, A. A. G. Proc. IEEE 2003, 91, 1922.
5. (a) Lehn, J. M. Supramolecular Chemistry: Concept and Perspectives; VCH: Weinheim, Germany, 1995.
6. (b) Desiraju, G. R. Crystal engineering, the design of organic solids; Elsevier: Amsterdam, 1989.
7. (a) Love, J. C.; Estroff, L. A.; Knebel, J. K.; Nuzzo, R. G.; Whitesides, G. M. Chem. Rev, 2005, 105, 1103.
8. (b) Scudiero, L.; Hipps, K. W.; Barlow, D. E. J. Phys. Chem. B 2003, 107, 2903.
9. (c) Non, J.; Ito, E.; Nakajima, K.; Kim, J.; Lee, H.; Hara, M. J. Phys. Chem. B 2002, 106, 7139.
10. (d) Eichhorst-Gerner, K.; Stabel, A.; Moessner, G.; Declerq, D.; Valiyaveettil, S.; Enkelmann, V.; Müllen, K.; Rabe, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1492.
11. (a) Bai, C. L. Scanning Tunneling Microscopy and its Applications; Springer: Shanghai, 1995.
12. (b) Chiang, S. Chem. Rev. 1997, 97, 1083.
13. (c) Moffart, T. P. In Scanning Tunneling Microscopy of Metal Electrodes in Electroanalytical Chemistry; Bard, A. J., Rubinstein, I., Eds.; Marcel Dekker: New York, 1999; Vol. 21.
14. (d) Rabe, J. P. Angew. Chem., Int. Ed. Engl. 1998, 28, 117.
15. (e) Wano, H.; Uosaki, K. Langmuir 2005, 21, 4024.
16. (a) Xu, S.-L.; Yin, S.-X.; Liang, H.-P.; Wang, C.; Wan, L.-J.; Bai, C.-L. J. Phys. Chem. B 2004, 108, 620.
17. (b) Yin, S.; Wang, C.; Qiu, X.; Xu, B.; Bai, C.-L. Surf. Interface Anal. 2001, 32, 248.
18. (c) Venkataraman, B.; Breen. J. J.; Flynn, G. W. J. Phys. Chem. 1995, 99, 6608.
19. (d) Rabe, J. P.; Buchholz, L. Science 1991, 253, 424.
20. (a) Zhang, J.; Gesquiere, A.; Sieffert, M.; Klapper, M.; Müllen, K.; De Schryver, F. C.; De Feyter, S. Nano Lett. 2005, 5, 1395.
21. (b) De Feyter, S.; De Schryver, F. C. J. Phys. Chem. B 2005, 109, 4290.
22. (c) Gong, J.-R.; Lei, S.-B.; Wan, L.-J.; Deng, G.-J.; Fan, Q.-H.; Bai, C.-L. Chem. Mater. 2003, 15, 3098.
23. (d) Stabel, A.; Heinz, R.; Rabe, J. P.; Wegner, G.; De Schryver, F. C.; Corens, D.; Dehaen, W.; Süling, C. J. Phys. Chem. 1995, 99, 8690.
24. (a) Lei, S.-B.; Wan, L.-J.; Wang, C.; Bai, C.-L. Adv. Mater. 2004, 16, 828.
25. (b) Han, M.-J.; Wan, L.-J.; Lei, S.-B.; Li, H.-M.; Fan, X.-L.; Bai, C.-L.; Li, Y.-L.; Zhu, D.-B. J. Phys. Chem. B 2004, 108, 965.
26. (c) Gong, J.-R.; Zhao, J.-L.; Lei, S.-B.; Wan, L.-J.; Bo, Z.-S.; Fan, X.-L.; Bai, C.-L. Langmuir 2003, 19, 10128.
27. (d) Mena-Osteritz, E. Adv. Mater. 2002, 14, 609.
28. (a) Ruben, M. Angew. Chem., Int. Ed. Engl. 2005, 44, 1594.
29. (b) Zell, P.; Mögele, F.; Ziener, U.; Rieger, B. Chem. Commun. 2005, 1294.
30. (c) Gong, J.-R.; Wan, L.-J.; Yuan, Q.-H.; Bai, C.-L.; Jude, H.; Stang, P. J. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 971.
31. (d) Scudiero, L.; Hipps, K. W.; Barlow, D. E. J. Phys. Chem B 2003, 107, 2903.
32. (a) Lu, J.; Lei, S.-B.; Zeng, Q.-D.; Kang, S.-Z.; Wang, C.; Wan, L.-J.; Bai, C.-L. J. Phys. Chem. B 2004, 108, 5161.
33. (b) Pan, G.-B.; Liu, J.-M.; Zhang, H.-M.; Wan, L.-J.; Zeng, Q.-D.; Bai, C.-L. Angew. Chem., Int. Ed. Engl. 2003, 42, 2747.
34. (c) Pan, G.-B.; Bu, J.-H.; Wang, D.; Liu, J.-M.; Wan, L.-J.; Zeng, Q.-D.; Bai, C.-L. J. Phys. Chem B 2003, 107, 13111.
35. (d) Pan, G.-B.; Wan, L.-J.; Zeng, Q.-D.; Bai, C.-L. Chem. Phys. Lett. 2003, 367, 711.
36. (a) Morgan, G. T.; Tunstall, R. H. J. Chem. Soc. 1924, 125, 1963.
37. (b) Mikhailov, B. M. Pure Appl. Chem. 1977, 49, 749.
38. (c) Lappert, M. F. Chem. Rev. 1956, 56, 959.
39. Fabian, J.; Hartmann, H. J. Phys. Org. Chem. 2004, 17, 359.
40. Görlitz, G.; Hartmann, H.; Kossanyi, J.; Valat, P.; Wintgens, V. Ber. Bunsen-Ges. Phys. Chem. 1998, 102, 1449.
41. Görlitz, G. Ph.D. Thesis, University Halle-Wittenberg, Germany, 1997.
42. Hartmann, H.; Hultzsch, R.; Ilge, H. D.; Friedrich, B.; Hebenstreit, J.; Fassler, D.; Meinel, U. DD 225884, 1985;
43. Chem. Abst. 1986, 104, 139107.
44. (a) Hunze, A.; Kanitz, A.; Hartmann, H.; Ronde, D. WO 02/065600;
45. Chem. Abstr. 2003, 137, 187010.
46. (b) Halm, J. M.; DeLorme, J. H. Photogr. Sci. Eng. 1979, 23, 252.
47. (a) Kammler, R.; Bourhill, G.; Yin, Y.; Bräuchler, C.; Görlitz, G.; Hartmann, H. J. Chem. Soc., Faraday Trans. 1996, 92, 945.
48. (b) Halik, M.; Wenseleers, W.; Grasso, C.; Stellacci, F.; Zojer, E.; Barlow, S.; Brédas, J.-L.; Perry, J. W.; Marder, S. R. Chem. Commun. 2003, 1490.
49. Halik, M.; Hartmann, H. Chem. Ew. J. 1999, 5, 2511.
50. Domercq, B.; Grasso, C.; Maldonado, J.-L.; Halik, M.; Barlow, S.; Marder, S. R.; Kippelen, B. J. Phys. Chem. B 2004, 108, 8647.
51. Sun, Y.-M.; Liu, Y.-Q.; Rohde, D.; Wan, L.-J. Adv. Funct. Mater. 2005, submitted.
52. Spec, A. L. J. Appl. Crystallogr. 2003, 36, 7.
53. Thalladi, V. R.; Weiss, H.-C.; Bläser, D.; Boese, R.; Nangia, A.; Desiraju, G. R. J. Am. Chem. Soc. 1998, 120, 8702.
54. (a) Steiner, T. Angew. Chem., Int, Ed. Engt. 2002, 41, 48.
55. (b) Desiraju, G. R. Acc. Chem. Res. 2002, 35, 565.
56. (c) Desiraju, G. R.; Steiner, T. The Weak Hydrogen Bond. In Structural Chemistry and Biology; Oxford University Press: Oxford, U.K., 1999.
57. (a) Chan, M. C. W.; Kui, S. C. F.; Cole, J. M.; McIntyre, G. J.; Matsui, S.; Zhu, N.; Tarn K.-H. Chem. Eur. J. 2005, 12, 2607.
58. (b) Kui, S. C. F.; Zhu, N.; Chan, M. C. W. Angew. Chem., Int. Ed. 2003, 42, 1628.
59. (a) Brammer, L.; Zordan. F.; Espallargas, G. M.; Purver, S. L.; Marin, L. A.; Adams, H.; Sherwood, P. ACA Trans. 2004, 39, 114.
60. (b) Brammer, L.; Bruton, E. A.; Sherwood, P. Cryst. Growth Des. 2001, 1, 277.
61. (c) Brammer, L.; Bruton, E. A.; Sherwood, P. New J. Chem. 1999, 23, 965.
62. (d) van den Berg, J. A.; Seddon, K. R., Cryst. Growth Des. 2003, 3, 643.
63. (a) Mirochnik, A. G.; Bukvetskii, B. V.; Gukhman, E. V.; Karasev, V. E. J. Fluorescence 2003,13, 157.
64. (b) Dromzée, Y.; Kossanyi, J.; Wintgens, V.; Valat, P.; Hartmann, H.; Görlitz, G. Z. Kristallogr. 1997, 212, 372.
65. (c) Böhme, U.; Hartmann, H.; Görlitz, G. Z. Kristallogr. 1996, 211, 133.
66. (d) Böhme, U.; Hartmann, H.; Görlitz, G. Z. Kristallogr. 1996, 211, 953.
67. (e) Hanson, A. W.; Macaulay, E. W. Acta Crystallogr. 1972, 28, 1961.
68. (a)Rossmeisl, J.; Hinnemann, B.; Jacobsen, K. W.;Nørskov, J. K.; Olsen, O. H.; Pedersen, J. T. J. Chem. Phys. 2003, 118, 9783.
69. (b) Tsuzuki, S.; Lüthi, H. P. J. Chem. Phys. 2001, 114, 3949.
70. Rohde, D. Ph.D. Thesis, University Halle-Wittenberg, Germany 2002.