Dendritic oligothiophenes terminated with tris(alkyloxy)phenylethynyl tails: Synthesis, physical properties, and self-assembly

Chemistry - A European Journal

Volumn 17, Issue 5, 2011, Pages 1507-1518

  Ma, Chang Qi ^a   Pisula, Wojciech ^b   Weber, Cornelia ^a   Feng, Xin Liang ^b   Müllen, Klaus ^b  

^a UNIVERSITY OF ULM   (Germany)

^b MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

Author keywords

dendrimers; liquid crystals; oligothiophenes; pi conjugation; self assembly

Indexed keywords

BULK STATE; COLUMNAR PHASIS; COLUMNAR STACKS; DIVERGENT APPROACH; FUNCTIONALIZED; LIQUID CRYSTALLINE DENDRIMERS; OLIGOTHIOPHENES; ORDERED STRUCTURES; PHENYLETHYNYL; PHENYLETHYNYL GROUPS; PI CONJUGATION; REDSHIFTED ABSORPTION; SIDE CHAINS; SONOGASHIRA COUPLING REACTIONS; STACKING INTERACTION; STRUCTURAL STUDIES; SUPRAMOLECULAR ORGANIZATIONS; SUZUKI COUPLING REACTION; THIRD GENERATION; THREE-DIMENSIONAL (3D); WIDE ANGLE X-RAY SCATTERING;

ABSORPTION; ABSORPTION SPECTROSCOPY; CATALYSIS; CRYSTALS; CYCLIC VOLTAMMETRY; DENDRIMERS; ELECTROCHEMICAL PROPERTIES; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; FUNCTIONAL POLYMERS; LIQUID CRYSTALS; ORGANIC POLYMERS; PHASE SEPARATION; THIOPHENE; THREE DIMENSIONAL;

SELF ASSEMBLY;

EID: 79251638273     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201002198     Document Type: Article

References (91)

1. For a special issue on organic electronics, see:, Y. Yang, F. Wudl, Adv. Mater. 2009, 21, 1401-1403.
2. B. S. Ong, Y. Wu, Y. Li, P. Liu, H. Pan, Chem. Eur. J. 2008, 14, 4766-4778
3. S. Allard, M. Forster, B. Souharce, H. Thiem, U. Scherf, Angew. Chem. 2008, 120, 4138-4167
4. Angew. Chem. Int. Ed. 2008, 47, 4070-4098.
5. A. C. Grimsdale, K. Leok Chan, R. E. Martin, P. G. Jokisz, A. B. Holmes, Chem. Rev. 2009, 109, 897-1091
6. S. Beaupré, P.-L. T. Boudreault, M. Leclerc, Adv. Mater. 2010, 22, E 6 -E 27.
7. L.-M. Chen, Z. Hong, G. Li, Y. Yang, Adv. Mater. 2009, 21, 1434-1449.
8. S. Liu, W. M. Wang, A. L. Briseno, S. C. B. Mannsfeld, Z. Bao, Adv. Mater. 2009, 21, 1217-1232.
9. F. C. Grozema, L. D. A. Siebbeles, Int. Rev. Phys. Chem. 2008, 27, 87-138
10. M. Kastler, W. Pisula, F. Laquai, A. Kumar, R. J. Davies, S. Baluschev, M. C. Garcia-Gutiérrez, D. Wasserfallen, H. J. Butt, C. Riekel, G. Wegner, K. Müllen, Adv. Mater. 2006, 18, 2255-2259.
11. Y. Shimizu, K. Oikawa, K.-i. Nakayama, D. Guillon, J. Mater. Chem. 2007, 17, 4223-4229
12. J. M. Warman, A. M. Vana Dea Craats, Mol. Cryst. Liq. Cryst. 2003, 396, 41-72
13. Z. Chen, A. Lohr, C. R. Saha-Moller, F. Wurthner, Chem. Soc. Rev. 2009, 38, 564-584
14. S. Sergeyev, W. Pisula, Y. H. Geerts, Chem. Soc. Rev. 2007, 36, 1902-1929
15. S. Laschat, A. Baro, N. Steinke, F. Giesselmann, C. Hägele, G. Scalia, R. Judele, E. Kapatsina, S. Sauer, A. Schreivogel, M. Tosoni, Angew. Chem. 2007, 119, 4916-4973
16. Angew. Chem. Int. Ed. 2007, 46, 4832-4887
17. W. Pisula, M. Zorn, J. Y. Chang, K. Müllen, R. Zentel, Macromol. Rapid Commun. 2009, 30, 1179-1202.
18. J. Roncali, P. Leriche, A. Cravino, Adv. Mater. 2007, 19, 2045-2060.
19. S. Roquet, A. Cravino, P. Leriche, O. Alévêque, P. Frére, J. Roncali, J. Am. Chem. Soc. 2006, 128, 3459-3466
20. W. Cui, Y. Fu, Y. Qu, H. Tian, J. Zhang, Z. Xie, Y. Geng, F. Wang, Chem. Asian J. 2010, 5, 932-940
21. J.-L. Wang, Z.-M. Tang, Q. Xiao, Y. Ma, J. Pei, Org. Lett. 2009, 11, 863-866.
22. X. B. Sun, Y. Q. Liu, S. Y. Chen, W. F. Qiu, G. Yu, Y. Q. Ma, T. Qi, H. J. Zhang, X. J. Xu, D. B. Zhu, Adv. Funct. Mater. 2006, 16, 917-925
23. X. Sun, Y. Zhou, W. Wu, Y. Liu, W. Tian, G. Yu, W. Qiu, S. Chen, D. Zhu, J. Phys. Chem. B 2006, 110, 7702-7707
24. T. Benincori, M. Capaccio, F. D. Angelis, L. Falciola, M. Muccini, P. Mussini, A. Ponti, S. Toffanin, P. Traldi, F. Sannicol, Chem. Eur. J. 2008, 14, 459-471.
25. A. J. Zucchero, P. L. McGrier, U. H. F. Bunz, Acc. Chem. Res. 2010, 43, 397-408
26. X. Zhang, X. Jiang, J. Luo, C. Chi, H. Chen, J. Wu, Chem. Eur. J. 2010, 16, 464-468
27. H. Uoyama, K. S. Kim, K. Kuroki, J.-Y. Shin, T. Nagata, T. Okujima, H. Yamada, N. Ono, D. Kim, H. Uno, Chem. Eur. J. 2010, 16, 4063-4074
28. A. Zen, P. Pingel, F. Jaiser, D. Neher, J. Grenzer, W. Zhuang, J. P. Rabe, A. Bilge, F. Galbrecht, B. S. Nehls, T. Farrell, U. Scherf, R. D. Abellon, F. C. Grozema, L. D. A. Siebbeles, Chem. Mater. 2007, 19, 1267-1276
29. A. Zen, A. Bilge, F. Galbrecht, R. Alle, K. Meerholz, J. Grenzer, D. Neher, U. Scherf, T. Farrell, J. Am. Chem. Soc. 2006, 128, 3914-3915
30. A. Bilge, A. Zen, M. Forster, H. Li, F. Galbrecht, B. S. Nehls, T. Farrell, D. Neher, U. Scherf, J. Mater. Chem. 2006, 16, 3177-3182.
31. P. L. Burn, S. C. Lo, I. D. W. Samuel, Adv. Mater. 2007, 19, 1675-1688
32. S. C. Lo, P. L. Burn, Chem. Rev. 2007, 107, 1097-1116.
33. S. M. Grayson, J. M. J. Fréchet, Chem. Rev. 2001, 101, 3819-3868.
34. J. Wu, A. C. Grimsdale, K. Müllen, J. Mater. Chem. 2005, 15, 41-52.
35. S. K. Deb, T. M. Maddux, L. Yu, J. Am. Chem. Soc. 1997, 119, 9079-9080.
36. J. S. Moore, Acc. Chem. Res. 1997, 30, 402-413.
37. J.-L. Wang, J. Yan, Z.-M. Tang, Q. Xiao, Y. Ma, J. Pei, J. Am. Chem. Soc. 2008, 130, 9952-9962.
38. C. Xia, X. Fan, J. Locklin, R. C. Advincula, Org. Lett. 2002, 4, 2067-2070
39. C.-Q. Ma, E. Mena-Osteritz, T. Debaerdemaeker, M. M. Wienk, R. A. J. Janssen, P. Bäuerle, Angew. Chem. 2007, 119, 1709-1713
40. Angew. Chem. Int. Ed. 2007, 46, 1679-1683.
41. K. Albrecht, K. Yamamoto, J. Am. Chem. Soc. 2009, 131, 2244-2251
42. Z. Zhao, J.-H. Li, X. Chen, X. Wang, P. Lu, Y. Yang, J. Org. Chem. 2009, 74, 383-395.
43. G. W. Kim, M. J. Cho, Y.-J. Yu, Z. H. Kim, J.-I. Jin, D. Y. Kim, D. H. Choi, Chem. Mater. 2007, 19, 42-50.
44. S. Rosenfeldt, N. Dingenouts, D. Pötschke, M. Ballauff, A. J. Berresheim, K. Müllen, P. Lindner, Angew. Chem. 2004, 116, 111-114
45. Angew. Chem. Int. Ed. 2004, 43, 109-112.
46. D. Liu, S. D. Feyter, M. Cotlet, U.-M. Wiesler, T. Weil, A. Herrmann, K. Mullen, F. C. Dea Schryver, Macromolecules 2003, 36, 8489-8498
47. C. G. Clark Jr., R. J. Wenzel, E. V. Andreitchenko, W. Steffen, R. Zenobi, K. Müllen, J. Am. Chem. Soc. 2007, 129, 3292-3301
48. K. L. Walker, M. S. Kahr, C. L. Wilkins, Z. Xu, J. S. Moore, J. Am. Soc. Mass Spectrom. 1994, 5, 731-739
49. C.-Q. Ma, M. Wunderlin, P. Bäuerle, unpublished results
50. C.-Q. Ma, E. Mena-Osteritz, P. Bäuerle, unpublished results.
51. C. G. Clark a Jr, R. J. Wenzel, E. V. Andreitchenko, W. Steffen, R. Zenobi, K. Müllen, New J. Chem. 2007, 31, 1300-1306.
52. A. Mishra, C.-Q. Ma, P. Bäuerle, Chem. Rev. 2009, 109, 1141-1276
53. M. Leclerc, M. Faàd, Adv. Mater. 1997, 9, 1087-1094
54. J. Roncali, Chem. Rev. 1997, 97, 173-206
55. Handbook of Thiophene-Based Materials (Eds.:, I.a F. Perepichka, D.a F. Perepichka,), Wiley, 2009, pp.a 910.
56. Y. Li, Y. Zou, Adv. Mater. 2008, 20, 2952-2958
57. I. F. Perepichka, D. F. Perepichka, H. Meng, F. Wudl, Adv. Mater. 2005, 17, 2281-2305.
58. C. Xia, X. Fan, J. Locklin, R. C. Advincula, A. Gies, W. Nonidez, J. Am. Chem. Soc. 2004, 126, 8735-8743.
59. C.-Q. Ma, M. Fonrodona, M. C. Schikora, M. M. Wienk, R. A. J. Janssen, P. Bäuerle, Adv. Funct. Mater. 2008, 18, 3323-3331
60. W. J. Mitchell, N. Kopidakis, G. Rumbles, D. S. Ginley, S. E. Shaheen, J. Mater. Chem. 2005, 15, 4518-4528
61. N. Kopidakis, W. J. Mitchell, J. vana dea Lagemaat, D. S. Ginley, G. Rumbles, S. E. Shaheen, W. L. Rance, Appl. Phys. Lett. 2006, 89, 103524-3
62. W. J. Mitchell, A. J. Ferguson, M. E. Kose, B. L. Rupert, D. S. Ginley, G. Rumbles, S. E. Shaheen, N. Kopidakis, Chem. Mater. 2009, 21, 287-297
63. N. Negishi, Y. Ie, M. Taniguchi, T. Kawai, H. Tada, T. Kaneda, Y. Aso, Org. Lett. 2007, 9, 829-832.
64. M. K. R. Fischer, T. E. Kaiser, F. Würthner, P. Bäuerle, J. Mater. Chem. 2009, 19, 1129-1141
65. M. K. R. Fischer, I. Lopez-Duarte, M. M. Wienk, M. V. Martinez-Diaz, R. A. J. Janssen, P. Bäuerle, T. Torres, J. Am. Chem. Soc. 2009, 131, 8669-8676.
66. M. K. R. Fischer, C.-Q. Ma, R. A. J. Janssen, T. Debaerdemaeker, P. Bäuerle, J. Mater. Chem. 2009, 19, 4784-4795.
67. W. W. H. Wong, C.-Q. Ma, W. Pisula, X. Feng, D. J. Jones, K. Müllen, R. A. J. Janssen, P. Bäuerle, A. B. Holmes, Chem. Mater. 2010, 22, 457-466
68. M. K. R. Fischer, S. Wenger, M. Wang, A. Mishra, S. M. Zakeeruddin, M. Grätzel, P. Bäuerle, Chem. Mater. 2010, 22, 1836-1845.
69. H. Meier, M. Lehmann, Angew. Chem. 1998, 110, 666-669
70. D. J. Pesak, J. S. Moore, Angew. Chem. 1997, 109, 1709-1712
71. Angew. Chem. Int. Ed. 1997, 36, 1636-1639.
72. J. Wu, M. D. Watson, L. Zhang, Z. Wang, K. Müllen, J. Am. Chem. Soc. 2004, 126, 177-186.
73. A. Mishra, C.-Q. Ma, R. A. J. Janssen, P. Bäuerle, Chem. Eur. J. 2009, 15, 13521-13534.
74. T. Johansson, W. Mammo, M. Svensson, M. R. Andersson, O. Inganäs, J. Mater. Chem. 2003, 13, 1316-1323.
75. W. Pisula, F. Dierschke, K. Mullen, J. Mater. Chem. 2006, 16, 4058-4064
76. J. L. Hutter, J. Bechhoefer, J. Cryst. Growth 2000, 217, 332-343.
77. W. Pisula, M. Kastler, D. Wasserfallen, T. Pakula, K. Müllen, J. Am. Chem. Soc. 2004, 126, 8074-8075
78. M. L. Bushey, A. Hwang, P. W. Stephens, C. Nuckolls, J. Am. Chem. Soc. 2001, 123, 8157-8158.
79. W. Pisula, Å. TomoviÄ, C. Simpson, M. Kastler, T. Pakula, K. Müllen, Chem. Mater. 2005, 17, 4296-4303.
80. W. Pisula, M. Kastler, D. Wasserfallen, M. Mondeshki, J. Piris, I. Schnell, K. Müllen, Chem. Mater. 2006, 18, 3634-3640
81. Å. TomoviÄ, J. vanDongen, S. J. George, H. Xu, W. Pisula, P. Leclere, M. M. J. Smulders, S. Dea Feyter, E. W. Meijer, A. P. H. J. Schenning, J. Am. Chem. Soc. 2007, 129, 16190-16196
82. V. Percec, M. R. Imam, M. Peterca, D. A. Wilson, P. A. Heiney, J. Am. Chem. Soc. 2009, 131, 1294-1304.
83. W. Pisula, M. Kastler, B. E. Hamaoui, M.-C. García- Gutiérrez, R. J. Davies, C. Riekel, K. Müllen, ChemPhysChem 2007, 8, 1025-1028
84. D. Wasserfallen, M. Kastler, W. Pisula, W. A. Hofer, Y. Fogel, Z. Wang, K. Müllen, J. Am. Chem. Soc. 2006, 128, 1334-1339
85. N. Terasawa, H. Monobe, K. Kiyohara, Y. Shimizu, Chem. Commun. 2003, 1678-1679
86. H. Bock, A. Babeau, I. Seguy, P. Jolinat, P. Destruel, ChemPhysChem 2002, 3, 532-535.
87. V. S. K. Balagurusamy, G. Ungar, V. Percec, G. Johansson, J. Am. Chem. Soc. 1997, 119, 1539-1555
88. D. J. P. Yeardley, G. Ungar, V. Percec, M. N. Holerca, G. Johansson, J. Am. Chem. Soc. 2000, 122, 1684-1689.
89. W. L. F. Armarego, D. D. Perrin, Purification of Laboratory Chemicals, 4 th ed., Butterwirth-Heinemann, Oxford, 1999.
90. M. W. Andersen, B. Hildebrandt, G. Köter, R. W. Hoffmann, Chem. Ber. 1989, 122, 1777-1782.
91. R. Wu, J. S. Schumm, D. L. Pearson, J. M. Tour, J. Org. Chem. 1996, 61, 6906-6921.