A folded, secondary structure in step-growth oligomers from covalently linked, crowded aromatics

Journal of the American Chemical Society

Volumn 125, Issue 16, 2003, Pages 4870-4873

  Zhang, Wei ^a   Horoszewski, Dana ^a   Decatur, John ^a   Nuckolls, Colin ^a  

^a Columbia University ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SECONDARY STRUCTURES;

ASSOCIATION REACTIONS; CONFORMATIONS; DIMERS; HYDROGEN BONDS; MOLECULAR STRUCTURE;

OLIGOMERS;

AROMATIC COMPOUND; PHENETHYL ALCOHOL; TRIS(DODECYLOXY)PHENETHYL DERIVATIVE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CONCENTRATION RESPONSE; CONFORMATION; COVALENT BOND; DIMERIZATION; HYDROGEN BOND; NONHUMAN; OLIGOMERIZATION; PROTEIN FOLDING; PROTEIN MOTIF; PROTEIN SECONDARY STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0037462099     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja034001d     Document Type: Article

References (41)

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9. For leading references on discotic liquid crystals, see: (a) Guillon, D. Struct. Bonding 1999, 95, 41-82. (b) Chandrasekhar, S.; Prasad, S.; Krishna, A. Contemp. Phys. 1999, 40, 237-245. (c) Chandrasekhar, Ranganath, G. S. Rep. Prog. Phys. 1990, 53, 57-84. (d) Boden, N.; Bushby, R. J.; Clements, J.; Movaghar, B. J. Mater. Chem. 1999, 9, 2081-2086.
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11. 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. J. Chem. Soc., 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.
12. 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. J. Chem. Soc., 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.
13. 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. J. Chem. Soc., 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.
14. 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. J. Chem. Soc., 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.
15. 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. J. Chem. Soc., 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.
16. 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. J. Chem. Soc., 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.
17. 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. J. Chem. Soc., 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.
18. 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. J. Chem. Soc., 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.
19. 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. J. Chem. Soc., 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.
20. 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. J. Chem. Soc., 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.
21. 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. J. Chem. Soc., 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.
22. 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. J. Chem. Soc., 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.
23. Foldamers that utilize π-stacking: (a) see ref 1b.
24. (b) Lokey, R. S.; Iverson, B. L. Nature 1995. 375, 303-305.
25. (c) Tanatani, A.; Yamaguchi, K.; Azumaya, I.; Fukutomi, R.; Shudo, K.; Kagechika, H. J. Am. Chem. Soc. 1998, 120, 6433-6442.
26. Spectra and experimental procedures are contained in the Supporting Information.
27. By the method of: Schirch, P. F. T.; Boekelheide, V. J. Am. Chem. Soc. 1981, 103, 6873-6878.
28. Similar to: (a) Wallenfels, K.; Witzler, F.; Friedrich, K. Tetrahedron 1967, 23, 1845-1855.
29. (b) Anthony, J. E.; Khan, S. I.; Rubin, Y. Tetrahedron Lett. 1997, 38, 3499-3502.
30. A two-step oxidation sequence was used first to yield the bis(aldehyde) ((a) Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 7, 639-666) and then the bis(carboxylic acid) ((b) Lindgren, B. O.; Nilsson, T. Acta Chem. Scand. 1973, 27, 888).
31. A two-step oxidation sequence was used first to yield the bis(aldehyde) ((a) Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 7, 639-666) and then the bis(carboxylic acid) ((b) Lindgren, B. O.; Nilsson, T. Acta Chem. Scand. 1973, 27, 888).
32. By the method of: Xu, Y.; Miller, M. J. J. Org. Chem. 1998, 63, 4314-4322.
33. 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.
34. These side chains have proven useful in solubilizing other discotics; see refs 4i,j.
35. By the procedure of: Bothner-By, A. A.; Stephens, R. L.; Lee, J.; Warren, C. D.; Jeanloz, R. W. J. Am. Chem. Soc. 1984, 106, 811-813.
36. Bisson, A. P.; Carver, F. J.; Eggleston, D. S.; Haltiwanger, R. C.; Hunter, C. A.; Livingstone, D. L.; McCabe, J. F.; Rotger, C.; Rowan, A. E. J. Am. Chem. Soc. 2000, 122, 8856-8868.
37. For a dimer from a traditional discotic, see: Tsukruk, V. V.; Bengs, H.; Ringsdorf, H. Langmuir 1996, 12, 754-757.
38. For examples of discotic polymers, polymerized through their side chains, see: (a) Wang, T.; Yan, D.; Zhou, E.; Karthaus, O.; Ringsdorf, H. Polymer 1998, 39, 4509-4513. (b) Weck, M.; Dunn, A. R.; Matsumoto, K.; Coates, G. W.; Lobkovsky, E. B.; Grubbs, R. H. Angew. Chem., Int. Ed. 1999, 38, 2741-2745.
39. For examples of discotic polymers, polymerized through their side chains, see: (a) Wang, T.; Yan, D.; Zhou, E.; Karthaus, O.; Ringsdorf, H. Polymer 1998, 39, 4509-4513. (b) Weck, M.; Dunn, A. R.; Matsumoto, K.; Coates, G. W.; Lobkovsky, E. B.; Grubbs, R. H. Angew. Chem., Int. Ed. 1999, 38, 2741-2745.
40. By the method of: Claridge, T. D. W. High-Resolution NMR Techniques in Organic Chemistry; Pergamon: Amsterdam, 1999.
41. By the procedure of: Rance, M.; Sorenson, O. W.; Bodenhausen, G.; Wagner, G.; Ernst, R. R.; Wüthrich, K. Biochem. Biophys. Res. Commun. 1983, 117, 479-485.