Supramolecular polymerization and polymorphs of oligo(p-phenylene vinylene)-functionalized bis- and monoureas

Chemistry - A European Journal

Volumn 14, Issue 17, 2008, Pages 5246-5257

  Yagai, Shiki ^a,b   Kubota, Shun ^a   Iwashima, Tomoyuki ^a   Kishikawa, Keiki ^a   Nakanishi, Takashi ^b,c,d   Karatsu, Takashi ^a   Kitamura, Akihide ^a  

^a CHIBA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c NATIONAL INSTITUTE FOR MATERIALS SCIENCE   (Japan)

^d MAX PLANCK INSTITUTE OF COLLOIDS AND INTERFACES   (Germany)

Author keywords

Liquid crystals; Organogels; Self assembly; Supramolecular polymers; Ureas

Indexed keywords

ABS RESINS; AROMATIC COMPOUNDS; CHEMICAL REACTIONS; COLLOIDS; GELATION; GELS; HEAT TREATMENT; HYDROGEN; LIQUID CRYSTAL POLYMERS; MONOMERS; NANOSTRUCTURED MATERIALS; ORGANIC COMPOUNDS; ORGANIC SOLVENTS; POLYMERIZATION; POLYMERS; SOLVENTS; SUPRAMOLECULAR CHEMISTRY; UREA;

LIQUID CRYSTALS; ORGANOGELS; SELF-ASSEMBLY; SUPRAMOLECULAR POLYMERS; UREAS;

FUNCTIONAL POLYMERS;

EID: 52649097175     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200701782     Document Type: Article

References (119)

1. J. M. Lehn, Supramolecular Chemistry, Concepts and Perspectives, VCH, Weinheim (Germany), 1995.
2. G. M. Whitesides, B. Grzybowski, Science 2002, 295, 2418-2421.
3. a) M. Lee, B.-K. Cho, W.-C. Zin, Chem. Rev. 2001, 101, 3869-3892;
4. b) F. J. M. Hoeben, P. Jonkheijm, E. W. Meijer, A. P. H. J. Schenning, Chem. Rev. 2005, 105, 1491-1546;
5. c) A. P. H. J. Schenning, E. W. Meijer, Chem. Commun. 2005, 3245-3258;
6. d) J. W. W. Pisula, K. Müllen, Chem. Rev. 2007, 107, 718-747.
7. a) L. Brunsveld, B. J. Folmer, E. W. Meijer, R. P. Sijbesma, Chem. Rev. 2001, 101, 4071-4098;
8. b) J.-M. Lehn, Polym. Int. 2002, 51, 825-839;
9. c) A. Ciferri, Macromol. Rapid Commun. 2002, 23, 511-529;
10. d) S. Yagai, J. Photochem. Photobiol. C 2006, 7, 164-182.
11. a) P. Terech, R. G. Weiss, Chem. Rev. 1997, 97, 3133-3159;
12. b) J. H. van Esch, B. L. Feringa, Angew. Chem. 2000, 112, 2351-2354;
13. Angew. Chem. Int. Ed. 2000, 39, 2263-2266;
14. c) D. J. Abdallah, R. G. Weiss. Adv. Mater. 2000, 12, 1237-1247;
15. d) T. Ishi-i, S. Shinkai, Top. Curr. Chem. 2005, 258, 119-160;
16. e) A. Ajayaghosh, V. K. Praveen, Acc. Chem. Res. 2007, 40, 644-656;
17. f) N. M. Sangeetha, U. Maitra, Chem. Soc. Rev. 2005, 34, 821-836.
18. a) T. Kato, Supramol. Sci. 1996, 3, 53-59;
19. b) T. Kato, N. Mizoshita, K. Kanie, Macromol. Rapid Commun. 2001, 22, 797-814;
20. c) T. Kato, N. Mizoshita, K. Kishimoto, Angew. Chem. 2005, 118, 44-74;
21. Angew. Chem. Int. Ed. 2006, 45, 38-68.
22. a) T. Goodson III, W. Li, A. Gharavi, L. Yu, Adv. Mater. 1997, 9, 639-643;
23. b) M. R. Robinson, S. Wang, A. J. Heeger, G. C. Bazan, Adv. Funct. Mater. 2001, 11, 413-419;
24. c) D. S. Seferos, D. A. Banach, N. A. Alcantar, J. N. Israelachvili, G. C. Bazan, J. Org. Chem. 2004, 69, 1110-1119.
25. A. P. H. J. Schenning, P. Jonkheijm, F. J. M. Hoeben, J. Van Herrikhuyzen, S. C. J. Meskers, E. W. Meijer, L. M. Herz, C. Daniel, C. Silva, R. T. Phillips, R. H. Friend, D. Beljonne, A. Miura, S. De Feyter, M. Zdanowska, H. Uji-I, F. C. De Schryver, Z. Chen, F. Würthner, M. Mas-Torrent, D. Den Boer, M. Durkut, P. Hadley, Synth. Met. 2004, 147, 43-48.
26. a) A. El-ghayoury, E. Peeters, A. P. H. J. Schenning, E. W. Meijer, Chem. Commun. 2000, 1969-1970;
27. b) A. P. H. J. Schenning, P. Jonkheijm, E. Peeters, E. W. Meijer, J. Am. Chem. Soc. 2001, 123, 409-416;
28. c) A. P. H. J. Schenning, J. van Herrikhuyzen, P. Jonkheijm, Z. Chen, F. Würthner, E. W. Meijer, J. Am. Chem. Soc. 2002, 124, 10252-10253;
29. d) P. Jonkheijm, F. J. M. Hoeben, R. Kleppinger, J. Van Herrikhuyzen, A. P. H. J. Schenning, E. W. Meijer, J. Am. Chem. Soc. 2003, 125, 15941-15949;
30. e) F. J. M. Hoeben, L. M. Herz, C. Daniel, P. Jonkeijm, A. P. H. J. Schenning, C. Silva, S. C. J. Meskers, D. Beljonne, R. T. Phillips, R. H. Friend, E. W. Meijer, Angew. Chem. 2004, 116, 2010-2013;
31. Angew. Chem. Int. Ed. 2004, 43, 1976-1979;
32. f) F. Würthner, Z. Chen, F. J. M. Hoeben, P. Osswald, C.-C. You, P. Jonkheijm, J. V. Herrikhuyzen, A. P. H. J. Schenning, P. P. A. M. van der Schoot, E. W. Meijer, E. H. A. Beckers, S. C. J. Meskers, R. A. J. Janssen, J. Am. Chem. Soc. 2004, 126, 10611-10618;
33. g) A. Miura, P. Jonkheijm, S. De Feyter, A. P. H. J. Schenning, E. W. Meijer, F. C. D. Schryver, Small 2005, 1, 131-137;
34. h) C. R. L. P. N. Jeukens, P. Jonkheijm, F. J. P. Wijnen, J. C. Gielen, P. C. M. Christianen, A. P. H. J. Schenning, E. W. Meijer, J. C. Maan, J. Am. Chem. Soc. 2005, 127, 8280-8281;
35. i) F. J. M. Hoeben, M. J. Pouderoijen, A. P. H. J. Schenning, E. W. Meijer, Org. Biomol. Chem. 2006, 4, 4460-4462;
36. j) P. Jonkheijm, N. Stutzmann, Z. Chen, M. de Leeuw Dago, E. W. Meijer, A. P. H. J. Schenning, F. Würthner, J. Am. Chem. Soc. 2006, 128, 9535-9540.
37. P. G. A. Janssen, J. Vandenbergh, J. L. J. Van Dongen, E. W. Meijer, A. P. H. J. Schenning, J. Am. Chem. Soc 2007, 129, 6078-6079.
38. R. Iwaura, F. J. M. Hoeben, M. Masuda, A. P. H. J. Schenning, E. W. Meijer, T. Shimizu, J. Am. Chem. Soc 2006, 128, 13298-13304.
39. a) A. Ajayaghosh, S. J. George, J. Am. Chem. Soc. 2001, 123, 5148-5149;
40. b) A. Ajayaghosh, S. J. George, V. K. Praveen, Angew. Chem. 2003, 115, 346-349;
41. Angew. Chem. Int. Ed. 2003, 42, 332-335;
42. c) S. J. George, A. Ajayaghosh, Chem. Eur. J. 2005, 11, 3217-3227;
43. d) A. Ajayaghosh, S. J. George, A. P. H. J. Schenning, Top. Curr. Chem. 2005, 258, 83-118;
44. e) A. Ajayaghosh, R. Varghese, S. J. George, C. Vijayakumar, Angew. Chem. 2006, 118, 1159-1162;
45. Angew. Chem. Int. Ed. 2006, 45, 1141-1144;
46. f) A. Ajayaghosh, C. Vijayakumar, V. K. Praveen, S. S. Babu, R. Varghese, J. Am. Chem. Soc 2006, 128, 7174-7175;
47. g) V. K. Praveen, S. J. George, R. Varghese, C. Vijayakumar, A. Ajayaghosh, J. Am. Chem. Soc. 2006, 128, 7542-7550;
48. h) A. Ajayaghosh, V. K. Praveen, Acc. Chem. Res. 2007, 40, 644-656;
49. i) A. Ajayaghosh, V. K. Praveen, C. Vijayakumar, S. J. George, Angew. Chem. 2007, 119, 6376-6381;
50. Angew. Chem. Int. Ed. 2007, 46, 6260-6265;
51. j) A. Ajayaghosh, V. K. Praveen, C. Vijayakumar, Chem. Soc. Rev. 2008, 37, 109-122.
52. J. van Herrikhuyzen, S. J. George, M. R. J. Vos, N. A. J. M. Sommerdijk, A. Ajayaghosh, S. C. J. Meskers, A. P. H. J. Schenning, Angew. Chem. 2007, 119, 1857-1860;
53. Angew. Chem. Int. Ed. 2007, 46, 1825-1828.
54. a) P. Jonkheijm, M. Fransen, A. P. H. J. Schenning, E. W. Meijer, J. Chem. Soc. Perkin Trans. 2 2001, 1280-1286;
55. b) B. S. Gaylord, S. Wang, A. J. Heeger, G. C. Bazan, J. Am. Chem. Soc. 2001, 123, 6417-6418;
56. c) J. F. Hulvat, M. Sofos, K. Tajima, S. I. Stupp. J. Am. Chem. Soc. 2005, 127, 366-372;
57. d) F. J. M. Hoeben, I. O. Shklyarevskiy, M. J. Pouderoijen, H. Engelkamp, A. P. H. J. Schenning, P. C. M. Christianen, J. C. Maan, E. W. Meijer, Angew. Chem. 2006, 118, 1254-1258;
58. Angew. Chem. Int. Ed. 2006, 45, 1232-1236;
59. e) K. Tajima, L.-S. Li, S. I. Stupp, J. Am. Chem. Soc. 2006, 128, 5488-5495.
60. Stupp et al. reported a self-assembly of OPVs using the dendron-rod-coil molecular architecture; B. W. Messmore, J. F. Hulvat, E. D. Sone, S. I. Stupp, J. Am. Chem. Soc. 2004, 126, 14452-14458.
61. V. Percec, M. Glodde, T. K. Bera, Y. Miura, I. Shiyanovskaya, K. D. Singer, V. S. K. Balagurusamy, P. A. Heiney, I. Schnell, A. Rapp, H. W. Spiess, S. D. Hudson, H. Duan, Nature 2002, 419, 384-387.
62. a) J.-F. Eckert, J.-F. Nicoud, D. Guillon, J.-F. Nierengarten, Tetrahedron Lett. 2000, 41, 6411-6414;
63. b) J.-F. Eckert, U. Maciejczuk, D. Guillon, J.-F. Nierengarten, Chem. Commun. 2001, 1278-1279;
64. c) L. Plasseraud, L. G. Cuervo, D. Guillon, G. Suess-Fink, R. Deschenaux, D. W. Bruce, B. Donnio, J. Mater. Chem. 2002, 12, 2653-2658.
65. a) W.-Y. Yang, J.-H. Ahn, Y.-S. Yoo, N.-K. Oh, M. Lee, Nat. Mater. 2005, 4, 399-402;
66. b) T. Nakanishi, W. Schmitt, T. Michinobu, D. G. Kurth, K. Ariga, Chem. Commun. 2005, 5982-5984;
67. c) S. Yagai, Y. Monma, N. Kawauchi, T. Karatsu, A. Kitamura, Org. Lett. 2007, 9, 1137-1140;
68. d) H. Maeda, Y. Kusunose, M. Terasaki, Y. Ito, C. Fujimoto, R. Fujii, T. Nakanishi, Chem. Asian J. 2007, 2, 350-357;
69. e) S. Yagai, T. Kinoshita, M. Higashi, K. Kishikawa, T. Nakanishi, T. Karatsu and A. Kitamura, J. Am. Chem. Soc 2007, 129, 13277-13287;
70. f) S. Yagai, M. Ishii, T. Karatsu, A. Kitamura, Angew. Chem. 2007, 119, 8151-8155;
71. Angew. Chem. Int. Ed. 2007, 46, 8005-8009.
72. a) F. Lortie, S. Boileau, L. Bouteiller, C. Chassenieux, B. Deme, G. Ducouret, M. Jalabert, F. Laupretre, P. Terech, Langmuir 2002, 18, 7218-7222;
73. b) F. Lortie, S. Boileau, L. Bouteiller, Chem. Eur. J. 2003, 9, 3008-3014;
74. c) F. Lortie, S. Boileau, L. Bouteiller, C. Chassenieux, F. Laupretre, Macromolecules 2005, 38, 5283-5287;
75. d) L. Bouteiller, O. Colombani, F. Lortie, P. Terech, J. Am. Chem. Soc. 2005, 127, 8893-8898.
76. a) K. Hanabusa, K. Shimura, K. Hirose, M. Kimura, H. Shirai, Chem. Lett. 1996, 885-886;
77. b) J. van Esch, S. De Feyter, R. M. Kellogg, F. De Schryver, B. L. Feringa. Chem. Eur. J. 1997, 3, 1238-1243;
78. c) C. Shi, Z. Huang, S. Kilic, J. Xu, R. M. Enick, E. J. Beckman, A. J. Carr, R. E. Melendez, A. D. Hamilton, Science 1999, 286, 1540-1543;
79. d) J. Van Esch, F. Schoonbeek, M. De Loos, H. Kooijman, A. L. Spek, R. M. Kellogg, B. L. Feringa, Chem. Eur. J. 1999, 5, 937-950;
80. e) S. van der Laan, B. L. Feringa, R. M. Kellogg, J. van Esch. Langmuir 2002, 18, 7136-7140;
81. f) J. Brinksma, B. L. Feringa, R. M. Kellogg, R. Vreeker, J. van Esch, Langmuir 2000, 16, 9249-9255;
82. g) A. Gesquiere, M. M. S. Abdel-Mottaleb, S. De Feyter, F. C. De Schryver, F. Schoonbeek, J. van Esch, R. M. Kellogg, B. L. Feringa, A. Calderone, R. Lazzaroni, J. L. Bredas, Langmuir 2000, 16, 10385-10391;
83. h) G. Wang, A. D. Hamilton, Chem. Eur. J. 2002, 8, 19541961;
84. i) V. Simic, L. Bouteiller, M. Jalabert, J. Am. Chem. Soc. 2003, 125, 13148-13154;
85. j) M. Barboiu, S. Cerneaux, A. van der Lee, G. Vaughan, J. Am. Chem. Soc. 2004, 126, 3545-3550;
86. k) M. George, G. Tan, V. T. John, R. G. Weiss, Chem. Eur. J. 2005, 11, 3243-3254;
87. l) R. A. Koevoets, R. M. Versteegen, H. Kooijman, A. L. Spek, R. P. Sijbesma, E. W. Meijer, J. Am. Chem. Soc. 2005, 127, 2999-3003;
88. m) M. R. J. Vos, G. E. Jardl, A. L. Pallas, M. Breurken, O. L. J. van Asselen, P. H. H. Bomans, P. E. L. G. Ledere, P. M. Frederik, R. J. M. Nolte, N. A. J. M. Sommerdijk, J. Am. Chem. Soc. 2005, 127, 16768-16769;
89. n) O. J. Dautel, M. Robitzer, J.-P. Lere-Porte, F. Serein-Spirau, J. E. M. Joel, J. Am. Chem. Soc. 2006, 128, 16213-16223;
90. o) I.-H. Paik, D. Tapriyal, R. M. Enick, A. D. Hamilton, Angew. Chem. 2007, 119, 3348-3351;
91. Angew. Chem. Int. Ed. 2007, 46, 3284-3287.
92. a) K. Kishikawa, S. Nakahara, Y. Nishikawa, S. Kohmoto, M. Yamamoto, J. Am. Chem. Soc. 2005, 127, 2565-2571;
93. b) H. Takezoe, K. Kishikawa, E. Gorecka, J. Mater. Chem. 2006, 16, 2412-2416.
94. a) F. S. Schoonbeek, J. H. Van Esch, B. Wegewijs, D. B. A. Rep, M. P. De Haas, T. M. Klapwijk, R. M. Kellogg, B. L. Feringa, Angew. Chem. 1999, 111, 1486-1490;
95. Angew. Chem. Int. Ed. 1999, 38, 1393-1397;
96. b) A. Gesquiere, S. De Feyter, F. C. De Schryver, F. Schoonbeek, J. van Esch, R. M. Kellogg, B. L. Feringa, Nano Lett. 2001, 1, 201-206.
97. a) Y. Liu, Y. Li, L. Jiang, H. Gan, H. Liu, Y. Li, J. Zhuang, F. Lu, D. Zhu, J. Org. Chem. 2004, 69, 9049-9054;
98. b) F. Wurthner, B. Hanke, M. Lysetska, G. Lambright, G. S. Harms, Org. Lett. 2005, 7, 967-970;
99. c) C. Wang, D. Zhang, D. Zhu, J. Am. Chem. Soc. 2005, 127, 16372-16373.
100. The Meijer and Ajayaghosh groups prepared liquid-crystalline dendrimers and sensory assemblies of OPVs, respectively, by using urea or bisurea units: a) F. S. Precup-Blaga, A. P. H. J. Schenning, E. W. Meijer, Macromolecules 2003, 36, 565-572;
101. b) R. Varghese, S. J. George, A. Ajayaghosh, Chem. Commun. 2005, 593-595.
102. a) U. Beginn, S. Keinath, M. Möller, Liq. Cryst. 1997, 23, 35-41;
103. b) U. Beginn, G. Zipp, M. Möller, Chem. Eur. J. 2000, 6, 2016-2023;
104. c) S. Yagai, T. Nakajima, T. Karatsu, K. Saitow, A. Kitamura, J. Am. Chem. Soc. 2004, 126, 11500-11508;
105. d) S. Yagai, T. Nakajima, K. Kishikawa, S. Kohmoto, T. Karatsu, A. Kitamura, J. Am. Chem. Soc. 2005, 127, 11134-11139.
106. D. G. Whitten, Acc. Chem. Res. 1993, 26, 502-509.
107. M. Kasha, H. R. Rawls, M. A. El-Bayoumi, Pure Appl. Chem. 1965, 11, 371-392.
108. Note that the fluorescence spectrum of the molecularly dissolved state at 70°C is more structured relative to those in THF at 20°C (Figure 3a) due to the decrease in solvent polarity.
109. P. van der School in Supramolecular Polymers (Ed.: A. Ciferri), CRC Press, Baton Rouge, LA, 2005, pp. 77-106.
110. R. Luboradzki, O. Gronwald, A. Ikeda, S. Shinkai, Chem. Lett. 2000, 1148-1149.
111. -1, respectively, which are characteristic of the hydrogen-bonded urea groups. Additionally, the fluorescence spectra of the THF gel only showed the emission from π-π stacked chromophores.
112. To investigate the effect of π-π stacking interactions on gelation ability, bisurea 8 lacking OPV moieties was also subjected to a gelation test. Compound 8 only gelated n-hexane (minimum gelation concentration = 0.332 wt%), n-decane (0.160wt%), and dioxane (0.706 wt%). This result clearly shows the significant contribution of π-π stacking interactions on gelation. figure presented
113. Y. Mido, Spectrochim. Acta A 1973, 29, 431-438.
114. S. Laschat, A. Baro, N. Steinke, F. Giesselmann, C. Haegele, G. Scalia, R. Judele, E. Kapatsina, S. Sauer, A. Schreivogel, M. Tosoni, Angew. Chem. 2007, 119, 4916-4973;
115. Angew. Chem. Int. Ed. 2007, 46, 4832-4887.
116. For the XRD patterns of 1a and 1b in the columnar mesophases, unassignable broad diffractions are observed at around 21 Å (indicated by*).
117. C. Tschierske, J. Mater. Chem. 1998, 8, 1485-1508.
118. A is Avogadro's number, M and ρ are the molecular mass and the density of the compound, respectively, and V is the volume of the unit cell calculated on the basis of the XRD data and thickness of 0.47 nm.
119. F. S. Precup-Blaga, A. P. H. J. Schenning, E. W. Meijer, Macromolecules 2003, 36, 565-572.