Supramolecular helical fluid columns from self-assembly of homomeric dipeptides

Chemistry - A European Journal

Volumn 14, Issue 33, 2008, Pages 10462-10471

  Yelamaggad, Channabasaveshwar V ^a   Shanker, Govindaswamy ^a   Rao, R V Ramana ^b   Rao, Doddamane S Shankar ^a   Prasad, Subbarao Krishna ^a   Babu, Vommina V Suresh ^b  

^a CENTRE FOR NANO AND SOFT MATTER SCIENCES   (India)

^b BANGALORE UNIVERSITY   (India)

Author keywords

Amino acids; Gelation; Hydrogen bonds; Liquid crystals; Peptides

Indexed keywords

AMINATION; AMINES; AMINO ACIDS; CHIRALITY; COAGULATION; COLLOIDS; CRYSTALLOGRAPHY; CRYSTALS; DATA STORAGE EQUIPMENT; DICHROISM; ENANTIOMERS; ETHANOL; FOURIER TRANSFORM INFRARED SPECTROSCOPY; GELATION; HYDROGEN; LIGHT SOURCES; LIQUID CRYSTALS; OPTICAL PROPERTIES; ORGANIC ACIDS; SPECTRUM ANALYZERS; STEREOCHEMISTRY; SUPRAMOLECULAR CHEMISTRY;

CIRCULAR DICHROISMS; COLUMNAR PHASE; COLUMNAR STRUCTURES; DI PEPTIDES; DIASTEREOMERS; ELECTRICAL SWITCHING; FERROELECTRIC BEHAVIORS; FLUID COLUMNS; HELICAL STRUCTURES; HYDROGEN BONDINGS; LATTICE PLANES; LIPOPHILIC SEGMENTS; OPTICAL-; ORGANOGELS; PEPTIDE UNITS; PROTEINOGENIC AMINO ACIDS; SELF-ASSEMBLY; SEM STUDIES; SPECTRAL ANALYSES; SPONTANEOUS POLARIZATIONS; SUPRAMOLECULES;

HYDROGEN BONDS;

DIPEPTIDE;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; DIFFERENTIAL SCANNING CALORIMETRY; INFRARED SPECTROPHOTOMETRY; PHASE TRANSITION; SCANNING ELECTRON MICROSCOPY; SPECTROPHOTOMETRY; TEMPERATURE; X RAY DIFFRACTION;

CALORIMETRY, DIFFERENTIAL SCANNING; CIRCULAR DICHROISM; DIPEPTIDES; MICROSCOPY, ELECTRON, SCANNING; MODELS, CHEMICAL; MOLECULAR STRUCTURE; PHASE TRANSITION; SPECTROPHOTOMETRY; SPECTROPHOTOMETRY, INFRARED; TEMPERATURE; X-RAY DIFFRACTION;

EID: 56349151303     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801607     Document Type: Article

References (75)

1. a) J.-M. Lehn, Supramolecular Chemistry, Wiley-VCH, Weinheim, 1995;
2. b) O. Ikkala, G. ten Brinke, Science 2002, 295, 2407-2409.
3. S. Chandrasekhar, B. K. Sadashiva, K. A. Suresh, Pramana 1977, 9, 471-480.
4. a) R. J. Bushby, O. R. Lozman, Curr. Opin. Colloid Interface Sci. 2002, 7, 343-354;
5. b) S. Laschat, A. Baro, N. Steinke, F. Giesselmann, C. Hagele, G. Scalia, R. Judele, E. Kapatsina, S. Sauer, A. Schreivogel, M. Tosoni, Angew. Chem. 2007, 119, 4916-4973;
6. Angew. Chem. Int. Ed. 2007, 46, 4832-4887.
7. a) G. Pelzl, S. Diele, W. Weissflog, Adv. Mater. 1999, 11, 707-724;
8. b) R. Amaranatha Reddy, C. Tschierske, J. Mater. Chem. 2006, 16, 907-961.
9. M. Gharbia, A. Gharbi, H.-T. Nguyen, J. Malthete, Curr. Opin. Colloid Interface Sci 2002, 7, 312-325.
10. a) V. Percec, M. Glodde, T. K. Bera, Y Miura, I. Shiyanovskaya, K. D. Singer, V. S. K. Balagurusamy, P. A. Heiney, L. Schnell, A. Rapp, H.-W. Spiess, S. D. Hudson, H. Daun, Nature 2002, 417, 384-387;
11. b) H. Meier, M. Lehmann, Angew. Chem. 1998, 110, 666-669;
12. Angew. Chem. Int. Ed. 1998, 37, 643-645;
13. c) M. Marcos, R. Gimennez, J. L. Serrano, D. Bertrand, B. Heinrich, D. Guillon, Chem. Eur. J. 2001, 7, 1006-1013.
14. B. Chen, X. Zeng, U. Baumeister, G. Ungar, C. Tschierske, Science 2005, 307, 96-98.
15. a) M. Prehm, S. Diele, M. K. Das, C. Tschierske, J. Am. Chem. Soc. 2003, 125, 614-615;
16. b) X. Cheng, M. Prehm, M. K. Das, J. Kain, U. Baumeister, S. Diele, D. Leine, A. Blume, C. Tschierske, J. Am. Chem. Soc. 2003, 125, 10996-10996.
17. a) T. Kato, Science 2002, 295, 2414-2418;
18. b) For a recent review on columnar liquid crystals with hydrogen bonds, see: L. Brunsfeld, B. J. B. Folmer, E. W. Meijer, R. P. Sijbesma, Chem. Rev. 2001, 101, 4071-4097;
19. c) L. J. Prins, D. N. Reinhoudt, P. Timmerman, Angew. Chem. Int. Ed. 2001, 40, 2383-2426.
20. a) T.-Q. Nguyen, M. L. Bushey, L. E. Brus, C. Nuckolls, J. Am. Chem. Soc. 2002, 124, 15051-15054;
21. b) J. J. van Grop, J. A. J. M. Vekemans, E. W. Meijer, J Am. Chem. Soc. 2002, 124, 14759-14769;
22. c) R. I. Gearba, M. Lehmann, J. Levin, D. A. Ivanov, M. H. J. Koch, J. Barbera, M. G. Debije, J. Piris, Y. H. Greets, Adv. Mater. 2003, 15, 1614-1618;
23. d) K. Kishikawa, S. Nakahara, Y. Nishikawa, S. Kohmoto, M. Yamamoto, J. Am. Chem. Soc. 2005, 127, 2565-2571, and references therein;
24. e) V. Percec, C.-H. Ahn, T. K. Bera, G. Ungar, D. J. P. Yeardley, Chem. Eur. J. 1999, 5, 1070-1083.
25. a) J. van Gestel, A. R. A. Palmans, B. Titulaer, J. A. J. M. Vekemans, E. W. Meijer, J. Am. Chem. Soc. 2005, 127, 5490-5494;
26. b) C. Xue, X. Weng, J.-J. Ge, Z. Shen, H. Shen, M. J. Graham, K.-U. Jeong, H. Huang, D. Zhang, M. Guo, F. W. Harris, S. Z. D. Cheng, Chem. Mater. 2004, 16, 1014-1025;
27. c) M. L. Bushey, A. Hwang, P. W. Stephend, C. Nuckolls, Angew. Chem. 2002, 114, 2952-2955;
28. Angew. Chem. Int. Ed. 2002, 41, 2828-2831;
29. d) A. R. A. Palmans, J. A. J. M. Vekemans, E. E. Havinga, E. W. Meijer, Angew. Chem. 1997, 109, 2763-2765;
30. Angew. Chem. Int. Ed. Engl. 1997, 36, 2648-2651;
31. e) U. Kumar, T. Kato, J. M. J. Frechet, J. Am. Chem. Soc. 1992, 114, 6630-6639;
32. f) S. Qu, F. Li, H. Wang, B. Bai, C. Xu, L. Zhao, B. Long, M. Li, Chem. Mater. 2007, 19, 4839-4846.
33. W. Zhou, W. Gu, Y. Xu, C. S. Pecinovsky, D. L. Gin, Langmuir 2003, 19, 6346-6348.
34. a) V. Percec, M. R. Imam, T. K. Bera, V. S. K. Balaguruswamy, M. Peterca, P. A. Heiney, Angew. Chem. 2005, 117, 4817-4823;
35. Angew. Chem. Int. Ed. 2005, 44, 4739-4745;
36. b) V. Percec, T. K. Bera, M. Glodde, Q. Fu, V. S. K. Balagurusamy, P. A. Heiney, Chem. Eur. J. 2003, 9, 921-935.
37. J. Watanabe, Y. Takashina, Macromolecules 1991, 24, 3423-3426, and references therein.
38. a) V. Percec, A. E. Dulcey, V. S. K. Balaguruswamy, Y. Miura, J. Smidrkal, M. Peterca, S. Nummelin, U. Edlund, S. D. Hudson, P. A. Heiney, H. Duan, S. N. Magonov, S. Vinogradov, Nature 2004, 430, 764-768;
39. b) V. Percec, A. E. Dulcey, M. Peterca, M. Hies, J. Ladislaw, B. M. Rosen, U. Edlund, P. A. Heiney, Angew. Chem. 2005, 117, 6674-6679;
40. Angew. Chem. Int. Ed. 2005, 44, 6516-6521;
41. c) M. Peterca, V. Percec, A. E. Dulcey, S. Nummelin, S. Korey, M. Llies, P. A. Heiney, J. Am. Chem. Soc. 2006, 128, 6713-6720.
42. a) M. Nishii, T. Matsuoka, Y. Kamikawa, T Kato, Org. Biomol. Chem. 2005, 3, 875-880;
43. b) T. Kato, T. Matsuoka, M. Nishi, Kamikawa, K. Kanie, T. Nisjimura, E. Yashima, S. Ujiie, Angew. Chem. 2004, 116, 2003-2006;
44. Angew. Chem. Int. Ed. 2004, 43, 1969-1972;
45. c) T. Kato, N. Mizoshita, K. Kishimoto, Angew. Chem. 2006, 118, 44-74;
46. Angew. Chem. Int. Ed. 2006, 45, 38-68.
47. a) J. Venkatraman, S. C. Shankaramma, P. Balaram, Chem. Rev. 2001, 101, 3131-3152;
48. b) De. M. Chung, Y. Dou, P. Baldi, J. S. Nowick, A. C. Griffin, T. R. Britt, J. Am. Chem. Soc. 2005, 127, 9998-9999;
49. c) H. Shen, K.-U. Jeong, M.J. Graham, S. Leng, J. X. Zheng, H. Huang, M. Guo, F. W. Harris, S. Z. D. Cheng, Soft Matter 2006, 2, 232-242;
50. d) M. Suzuki, T. Sato, H. Shirai, K. Hanabusa, New J. Chem. 2006, 30, 1184-1191.
51. a) F. Morale, R. W. Date, D. Guillon, D. W. Bruce, R. L. Finn, C. Wilson, A. J. Blake, M. Schröder, B. Donnio, Chem. Eur. J. 2003, 9, 2484-2501.
52. a) A. V. Petukhov, D. van der Beek, R. P. A. Dullens, I. P. Dolbnya, G. V. Vroege, H. N. W. Lekkerkerker, Phys. Rev. Lett. 2005, 95, 77801-77804;
53. b) J. Barbera, R. Iglesias, J. L. Serrano, T. Sierra, M. R. de la Fuente, B. Palacios, M. A. Perez-Jubindo, J. T. Vazquez, J. Am. Chem. Soc. 1998, 120, 2908-2918.
54. M. Lehmann, G. Kestemont, R. Gómez Aspe, C. Buess-Hermann, M. H. J. Koch, M. G. Debije, J. Piris, M. P. de Haas, J. M. Warman, M. D. Watson, V. Lemaur, J. Cornil, Y. H. Geerts, R. Gearba, D. A. Ivanov, Chem. Eur. J. 2005, 11, 3349-3362.
55. B. Donnio, B. Heinrich, H. Allouchi, J. Kain, S. Diele, D. Guillon, D. W. Bruce, J. Am. Chem. Soc. 2004, 126, 15258-15268.
56. a) H. Bock, W. Helfrich, Liq. Cryst. 1992, 12, 697-703;
57. b) H. Bock, W. Helfrich, Liq. Cryst. 1995, 18, 387-399;
58. c) H. Bock, W. Helfrich, Liq. Cryst. 1995, 18, 707-713;
59. d) H. Takezoe, K. Kishikawa, E. Gorecka, J. Mater. Chem. 2006, 16, 2412-2416;
60. e) H. Kitzerow, C. Bahr, Chirality in Liquid Crystals, Springer, New York, 2001;
61. f) Topics in Stereochemistry: Materials-Chirality, Vol. 24 (Eds.: M. M. Green, R. J. M. Nolte, E. W. Meijer), Wiley, Hoboken, 2003, Chapter 6.
62. a) J. Malthete, A. Collet, J. Am. Chem. Soc. 1987, 109, 7544-7545;
63. b) A. Jakli, A. Saupe, Liq. Cryst. 1997, 22, 309-316.
64. A. G. Serrette, T. M. Swager, Angew. Chem. 1994, 106, 2378-2380;
65. Angew. Chem. Int. Ed. Engl. 1994, 33, 2342-2435.
66. M. Sawamura, K. Kawai, Y. Matsuo, K. Kanie, T. Kato, E. Nakamura, Nature 2002, 419, 702-705.
67. a) P. Terech, R. G. Weiss, Chem. Rev. 1997, 97, 3133-3159;
68. b) N. M. Sangeetha, U. Maitra, Chem. Soc. Rev. 2005, 34, 821-836.
69. a) N. Mizoshita, H. Monobe, M.. Inoue, M. Ukon, T. Watanabe, Y. Shimizu, K. Hanabusa, T. Kato, Chem. Commun. 2002, 428-429;
70. b) N. Mizoshita, Y. Suzuki, K. Kishimoto, K. Hanabusa, T. Kato, J. Mater. Chem. 2002, 12, 2197-2201;
71. c) F. Camerel, G. Ulrich, R. Ziessel, Org. Lett. 2004, 6, 4171-4174.
72. S. G. Lim, B. M. Jung, L. S. Lee, H. H. Song, C. Kim, Y. J. Chang, Chem. Mater. 2007, 19, 460-467, and references therein.
73. a) S. Kobayashi, N. Hamasaki, M. Suzuki, M. Kimura, H. Shirai, K. Hanabusa, J. Am. Chem. Soc. 2002, 124, 6550-6551;
74. b) Y. Yang, M. Nakazawa, M. Suzuki, H. Shirai, K. Hanabusa, J. Mater. Chem. 2007, 17, 2936-2943;
75. c) Y. Ono, K. Nakashima, M. Sano, Y. Kanekiyo, K. Inoue, H. Junichi, S. Shinkai, Chem. Commun. 1998, 1477-1478.