Synthesis, self-assembly, and switching of one-dimensional nanostructures from new crowded aromatics

Journal of the American Chemical Society

Volumn 125, Issue 27, 2003, Pages 8264-8269

  Bushey, Mark L ^a   Nguyen, Thuc Quyen ^a   Nuckolls, Colin ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CROWDED AROMATICS;

ATOMIC FORCE MICROSCOPY; ELECTRIC FIELD EFFECTS; NANOSTRUCTURED MATERIALS; SELF ASSEMBLY; SWITCHING; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION ANALYSIS;

AROMATIC COMPOUNDS;

ALKYNE; AMIDE; AROMATIC COMPOUND; BENZENE DERIVATIVE; NANOPARTICLE;

ARTICLE; ATOMIC FORCE MICROSCOPY; BIREFRINGENCE; CHEMICAL ANALYSIS; CRYSTAL STRUCTURE; DIFFERENTIAL SCANNING CALORIMETRY; ELECTRIC FIELD; ELECTRIC POTENTIAL; FILM; MICROSCOPY; POLARIZATION; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNCHROTRON; SYNTHESIS; X RAY DIFFRACTION;

EID: 0038682494     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja034783a     Document Type: Article

References (72)

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41. Hydrogen bonds used to stabilize π-stacks: (a) Matsunaga, Y.; Miyajima, N.; Nakayasu, Y.; Sakai, S.; Yonenaga, M. Bull. Chem. Soc. Jpn. 1988, 61, 207-210. (b) Brunsveld, L.; Zhang, H.; Glasbeek, M.; Vekemans, J. A. J. M.; Meijer, E. W. J. Am. Chem. Soc. 2000, 122, 6175-6182 and references therein. (c) Yasuda, Y.; Iishi, E.; Inada, H.; Shirota, Y. Chem. Lett. 1996, 7, 575-576. (d) Lightfoot, M. P.; Mair, F. S.; Pritchard, R. G.; Warren, J. E. Chem. Commun. 1999, 19, 1945-1946. (e) Ranganathan, D.; Kurur, S.; Gilardi, R.; Karle, I. L. Biopolymers 2000, 54, 289-295. (f) Paleos, C. M.; Tsiourvas, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1696-1711, and references therein. (g) Brienne, M. J.; Gabard, J.; Lehn, J. M.; Stibor, I. J. Chem., Soc., Chem. Commun. 1989, 24, 1868-70. (h) Goldmann, D.; Dietel, R.; Janietz, D.; Schmidt, C.; Wendorff, J. H. Liq. Cryst. 1998, 24, 407-411. (i) Ungar, G.; Abramic, D.; Percec, V.; Heck, J. A. Liq. Cryst. 1996, 21, 73-86. (j) Percec, V.; Ahn, C.-H.; Bera, T. K.; Ungar, G.; Yeardley, D. J. P. Chem.-Eur. J. 1999, 5, 1070-1083. (k) Malthete, J.; Levelut, A. M.; Liebert, L. Adv. Mater. 1992, 4, 37-41. (l) Pucci, D.; Veber, M.; Malthete, J. Liq. Cryst. 1996, 21, 153-155.
42. Hydrogen bonds used to stabilize π-stacks: (a) Matsunaga, Y.; Miyajima, N.; Nakayasu, Y.; Sakai, S.; Yonenaga, M. Bull. Chem. Soc. Jpn. 1988, 61, 207-210. (b) Brunsveld, L.; Zhang, H.; Glasbeek, M.; Vekemans, J. A. J. M.; Meijer, E. W. J. Am. Chem. Soc. 2000, 122, 6175-6182 and references therein. (c) Yasuda, Y.; Iishi, E.; Inada, H.; Shirota, Y. Chem. Lett. 1996, 7, 575-576. (d) Lightfoot, M. P.; Mair, F. S.; Pritchard, R. G.; Warren, J. E. Chem. Commun. 1999, 19, 1945-1946. (e) Ranganathan, D.; Kurur, S.; Gilardi, R.; Karle, I. L. Biopolymers 2000, 54, 289-295. (f) Paleos, C. M.; Tsiourvas, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1696-1711, and references therein. (g) Brienne, M. J.; Gabard, J.; Lehn, J. M.; Stibor, I. J. Chem., Soc., Chem. Commun. 1989, 24, 1868-70. (h) Goldmann, D.; Dietel, R.; Janietz, D.; Schmidt, C.; Wendorff, J. H. Liq. Cryst. 1998, 24, 407-411. (i) Ungar, G.; Abramic, D.; Percec, V.; Heck, J. A. Liq. Cryst. 1996, 21, 73-86. (j) Percec, V.; Ahn, C.-H.; Bera, T. K.; Ungar, G.; Yeardley, D. J. P. Chem.-Eur. J. 1999, 5, 1070-1083. (k) Malthete, J.; Levelut, A. M.; Liebert, L. Adv. Mater. 1992, 4, 37-41. (l) Pucci, D.; Veber, M.; Malthete, J. Liq. Cryst. 1996, 21, 153-155.
43. Hydrogen bonds used to stabilize π-stacks: (a) Matsunaga, Y.; Miyajima, N.; Nakayasu, Y.; Sakai, S.; Yonenaga, M. Bull. Chem. Soc. Jpn. 1988, 61, 207-210. (b) Brunsveld, L.; Zhang, H.; Glasbeek, M.; Vekemans, J. A. J. M.; Meijer, E. W. J. Am. Chem. Soc. 2000, 122, 6175-6182 and references therein. (c) Yasuda, Y.; Iishi, E.; Inada, H.; Shirota, Y. Chem. Lett. 1996, 7, 575-576. (d) Lightfoot, M. P.; Mair, F. S.; Pritchard, R. G.; Warren, J. E. Chem. Commun. 1999, 19, 1945-1946. (e) Ranganathan, D.; Kurur, S.; Gilardi, R.; Karle, I. L. Biopolymers 2000, 54, 289-295. (f) Paleos, C. M.; Tsiourvas, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1696-1711, and references therein. (g) Brienne, M. J.; Gabard, J.; Lehn, J. M.; Stibor, I. J. Chem., Soc., Chem. Commun. 1989, 24, 1868-70. (h) Goldmann, D.; Dietel, R.; Janietz, D.; Schmidt, C.; Wendorff, J. H. Liq. Cryst. 1998, 24, 407-411. (i) Ungar, G.; Abramic, D.; Percec, V.; Heck, J. A. Liq. Cryst. 1996, 21, 73-86. (j) Percec, V.; Ahn, C.-H.; Bera, T. K.; Ungar, G.; Yeardley, D. J. P. Chem.-Eur. J. 1999, 5, 1070-1083. (k) Malthete, J.; Levelut, A. M.; Liebert, L. Adv. Mater. 1992, 4, 37-41. (l) Pucci, D.; Veber, M.; Malthete, J. Liq. Cryst. 1996, 21, 153-155.
44. Hydrogen bonds used to stabilize π-stacks: (a) Matsunaga, Y.; Miyajima, N.; Nakayasu, Y.; Sakai, S.; Yonenaga, M. Bull. Chem. Soc. Jpn. 1988, 61, 207-210. (b) Brunsveld, L.; Zhang, H.; Glasbeek, M.; Vekemans, J. A. J. M.; Meijer, E. W. J. Am. Chem. Soc. 2000, 122, 6175-6182 and references therein. (c) Yasuda, Y.; Iishi, E.; Inada, H.; Shirota, Y. Chem. Lett. 1996, 7, 575-576. (d) Lightfoot, M. P.; Mair, F. S.; Pritchard, R. G.; Warren, J. E. Chem. Commun. 1999, 19, 1945-1946. (e) Ranganathan, D.; Kurur, S.; Gilardi, R.; Karle, I. L. Biopolymers 2000, 54, 289-295. (f) Paleos, C. M.; Tsiourvas, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1696-1711, and references therein. (g) Brienne, M. J.; Gabard, J.; Lehn, J. M.; Stibor, I. J. Chem., Soc., Chem. Commun. 1989, 24, 1868-70. (h) Goldmann, D.; Dietel, R.; Janietz, D.; Schmidt, C.; Wendorff, J. H. Liq. Cryst. 1998, 24, 407-411. (i) Ungar, G.; Abramic, D.; Percec, V.; Heck, J. A. Liq. Cryst. 1996, 21, 73-86. (j) Percec, V.; Ahn, C.-H.; Bera, T. K.; Ungar, G.; Yeardley, D. J. P. Chem.-Eur. J. 1999, 5, 1070-1083. (k) Malthete, J.; Levelut, A. M.; Liebert, L. Adv. Mater. 1992, 4, 37-41. (l) Pucci, D.; Veber, M.; Malthete, J. Liq. Cryst. 1996, 21, 153-155.
45. Hydrogen bonds used to stabilize π-stacks: (a) Matsunaga, Y.; Miyajima, N.; Nakayasu, Y.; Sakai, S.; Yonenaga, M. Bull. Chem. Soc. Jpn. 1988, 61, 207-210. (b) Brunsveld, L.; Zhang, H.; Glasbeek, M.; Vekemans, J. A. J. M.; Meijer, E. W. J. Am. Chem. Soc. 2000, 122, 6175-6182 and references therein. (c) Yasuda, Y.; Iishi, E.; Inada, H.; Shirota, Y. Chem. Lett. 1996, 7, 575-576. (d) Lightfoot, M. P.; Mair, F. S.; Pritchard, R. G.; Warren, J. E. Chem. Commun. 1999, 19, 1945-1946. (e) Ranganathan, D.; Kurur, S.; Gilardi, R.; Karle, I. L. Biopolymers 2000, 54, 289-295. (f) Paleos, C. M.; Tsiourvas, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1696-1711, and references therein. (g) Brienne, M. J.; Gabard, J.; Lehn, J. M.; Stibor, I. J. Chem., Soc., Chem. Commun. 1989, 24, 1868-70. (h) Goldmann, D.; Dietel, R.; Janietz, D.; Schmidt, C.; Wendorff, J. H. Liq. Cryst. 1998, 24, 407-411. (i) Ungar, G.; Abramic, D.; Percec, V.; Heck, J. A. Liq. Cryst. 1996, 21, 73-86. (j) Percec, V.; Ahn, C.-H.; Bera, T. K.; Ungar, G.; Yeardley, D. J. P. Chem.-Eur. J. 1999, 5, 1070-1083. (k) Malthete, J.; Levelut, A. M.; Liebert, L. Adv. Mater. 1992, 4, 37-41. (l) Pucci, D.; Veber, M.; Malthete, J. Liq. Cryst. 1996, 21, 153-155.
46. Hydrogen bonds used to stabilize π-stacks: (a) Matsunaga, Y.; Miyajima, N.; Nakayasu, Y.; Sakai, S.; Yonenaga, M. Bull. Chem. Soc. Jpn. 1988, 61, 207-210. (b) Brunsveld, L.; Zhang, H.; Glasbeek, M.; Vekemans, J. A. J. M.; Meijer, E. W. J. Am. Chem. Soc. 2000, 122, 6175-6182 and references therein. (c) Yasuda, Y.; Iishi, E.; Inada, H.; Shirota, Y. Chem. Lett. 1996, 7, 575-576. (d) Lightfoot, M. P.; Mair, F. S.; Pritchard, R. G.; Warren, J. E. Chem. Commun. 1999, 19, 1945-1946. (e) Ranganathan, D.; Kurur, S.; Gilardi, R.; Karle, I. L. Biopolymers 2000, 54, 289-295. (f) Paleos, C. M.; Tsiourvas, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1696-1711, and references therein. (g) Brienne, M. J.; Gabard, J.; Lehn, J. M.; Stibor, I. J. Chem., Soc., Chem. Commun. 1989, 24, 1868-70. (h) Goldmann, D.; Dietel, R.; Janietz, D.; Schmidt, C.; Wendorff, J. H. Liq. Cryst. 1998, 24, 407-411. (i) Ungar, G.; Abramic, D.; Percec, V.; Heck, J. A. Liq. Cryst. 1996, 21, 73-86. (j) Percec, V.; Ahn, C.-H.; Bera, T. K.; Ungar, G.; Yeardley, D. J. P. Chem.-Eur. J. 1999, 5, 1070-1083. (k) Malthete, J.; Levelut, A. M.; Liebert, L. Adv. Mater. 1992, 4, 37-41. (l) Pucci, D.; Veber, M.; Malthete, J. Liq. Cryst. 1996, 21, 153-155.
47. Hydrogen bonds used to stabilize π-stacks: (a) Matsunaga, Y.; Miyajima, N.; Nakayasu, Y.; Sakai, S.; Yonenaga, M. Bull. Chem. Soc. Jpn. 1988, 61, 207-210. (b) Brunsveld, L.; Zhang, H.; Glasbeek, M.; Vekemans, J. A. J. M.; Meijer, E. W. J. Am. Chem. Soc. 2000, 122, 6175-6182 and references therein. (c) Yasuda, Y.; Iishi, E.; Inada, H.; Shirota, Y. Chem. Lett. 1996, 7, 575-576. (d) Lightfoot, M. P.; Mair, F. S.; Pritchard, R. G.; Warren, J. E. Chem. Commun. 1999, 19, 1945-1946. (e) Ranganathan, D.; Kurur, S.; Gilardi, R.; Karle, I. L. Biopolymers 2000, 54, 289-295. (f) Paleos, C. M.; Tsiourvas, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1696-1711, and references therein. (g) Brienne, M. J.; Gabard, J.; Lehn, J. M.; Stibor, I. J. Chem., Soc., Chem. Commun. 1989, 24, 1868-70. (h) Goldmann, D.; Dietel, R.; Janietz, D.; Schmidt, C.; Wendorff, J. H. Liq. Cryst. 1998, 24, 407-411. (i) Ungar, G.; Abramic, D.; Percec, V.; Heck, J. A. Liq. Cryst. 1996, 21, 73-86. (j) Percec, V.; Ahn, C.-H.; Bera, T. K.; Ungar, G.; Yeardley, D. J. P. Chem.-Eur. J. 1999, 5, 1070-1083. (k) Malthete, J.; Levelut, A. M.; Liebert, L. Adv. Mater. 1992, 4, 37-41. (l) Pucci, D.; Veber, M.; Malthete, J. Liq. Cryst. 1996, 21, 153-155.
48. See ref 8 above.
49. Molecular modeling was performed using MacroModel v. 7.0 and the Amber* forcefield: Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467.
50. The preparation of 3 is contained in the Supporting Information and produced by methods similar to: (a) Wallenfels, K.; Witzler, F.; Friedrich, K. Tetrahedron 1967, 23, 1845-1855. (b) Anthony, J. E.; Khan, S. I.; Rubin, Y. Tetrahedron Lett. 1997, 38, 3499-3502. (c) Hennrich, G.; Lynch, V. M.; Anslyn, E. V. Chem.-Eur. J. 2002, 8, 2274-2278.
51. The preparation of 3 is contained in the Supporting Information and produced by methods similar to: (a) Wallenfels, K.; Witzler, F.; Friedrich, K. Tetrahedron 1967, 23, 1845-1855. (b) Anthony, J. E.; Khan, S. I.; Rubin, Y. Tetrahedron Lett. 1997, 38, 3499-3502. (c) Hennrich, G.; Lynch, V. M.; Anslyn, E. V. Chem.-Eur. J. 2002, 8, 2274-2278.
52. The preparation of 3 is contained in the Supporting Information and produced by methods similar to: (a) Wallenfels, K.; Witzler, F.; Friedrich, K. Tetrahedron 1967, 23, 1845-1855. (b) Anthony, J. E.; Khan, S. I.; Rubin, Y. Tetrahedron Lett. 1997, 38, 3499-3502. (c) Hennrich, G.; Lynch, V. M.; Anslyn, E. V. Chem.-Eur. J. 2002, 8, 2274-2278.
53. Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1980, 8, 627-630.
54. Farina, V.; Krishman, B. J. Am. Chem. Soc. 1991, 113, 9585-9595.
55. Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1989, 54, 5856-5866.
56. The preparation of tributyl(l-dodcynyl)tin is contained in the Supporting Information by a procedure similar. to: Ito, Y.; Inouye, M.; Yokota, H.; Murakami, M. J. Org. Chem. 1990, 55, 2567-2568.
57. Conditions to achieve a sparsely covered monolayer were found by varying the spin-rate, solvent, and concentration during spin-casting of 1c on the basal plane of HOPG by the methods used in ref 8c.
58. Nguyen, T.-Q., Bushey, M.; Martel, R.; Avouris, P.; Brus, L. E.; Nuckolls, C., unpublished results.
59. Micron-wide crystalline domains have been seen for discotic liquid crystals: (a) Lovinger, A. J.; Nuckolls, C.; Katz, T. J. J. Am. Chem. Soc. 1998, 120, 264-268. (b) van Gorp, J. J.; Vekemans, J. A. J. M.; Meijer, E. W. J. Am. Chem. Soc. 2002, 124, 14759-14769.
60. Micron-wide crystalline domains have been seen for discotic liquid crystals: (a) Lovinger, A. J.; Nuckolls, C.; Katz, T. J. J. Am. Chem. Soc. 1998, 120, 264-268. (b) van Gorp, J. J.; Vekemans, J. A. J. M.; Meijer, E. W. J. Am. Chem. Soc. 2002, 124, 14759-14769.
61. For similar calorimetry values, see the references cited in ref 1.
62. For similar micrographs from derivatives of 2, see ref 8a,b.
63. (a) Destrade, C.; Foucher, P.; Gasparoux, H.; Nguyen, H. T.; Levelut, A. M.; Malthete, J. Mol. Cryst. Liq. Cryst. 1984, 106, 121-146.
64. (b) Billard, J.; Dubois, J. C.; Nguyen H. T.; Zann, A. Nouv. J. Chim. 1978, 2, 535-540.
65. Zimmermann, H.; Bader, V.; Poupko, R.; Wachtel, E. J.; Luz, Z. J. Am. Chem. Soc. 2002, 124, 15286-15301.
66. (a) Hartshorne, N. H.; Stuart, A. Crystals and the Polarising Light Microscope, 3rd ed.; Edward Arnold Ltd.: London, 1960; p 290ff.
67. (b) Lovinger, A. J.; Nuckolls, C.; Katz, T. J. J. Am. Chem. Soc. 1998, 120, 264-268.
68. For many examples of these characteristic diffraction patterns for columnar discotics, see: (a) Levelut, A. M. J. Chim. Phys. Phys.-Chim. Biol. 1983, 80, 149-161 and (b) the citations in ref 1.
69. For many examples of these characteristic diffraction patterns for columnar discotics, see: (a) Levelut, A. M. J. Chim. Phys. Phys.-Chim. Biol. 1983, 80, 149-161 and (b) the citations in ref 1.
70. (a) Zimmermann, H.; Poupko, R.; Luz, Z.; Billard, J. Z. Naturforsch., A 1985, 40A, 149-160.
71. (b) See also ref 1g.
72. Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timniers, F. J. Organometallics 1996, 15, 1518-1520.