Review
Aniline Oligomers – Architecture, Function and New Opportunities for Nanostructured Materials
Zhixiang Wei,
Charl F. J. Faul,
Zhixiang Wei
National Center for Nanoscience and Technology, Beijing 100080, P. R. China
Search for more papers by this authorCorresponding Author
Charl F. J. Faul
Inorganic and Materials Chemistry, School of Chemistry, University of Bristol, BS8 1TS, UK
Inorganic and Materials Chemistry, School of Chemistry, University of Bristol, BS8 1TS, UK.Search for more papers by this authorZhixiang Wei,
Charl F. J. Faul,
Zhixiang Wei
National Center for Nanoscience and Technology, Beijing 100080, P. R. China
Search for more papers by this authorCorresponding Author
Charl F. J. Faul
Inorganic and Materials Chemistry, School of Chemistry, University of Bristol, BS8 1TS, UK
Inorganic and Materials Chemistry, School of Chemistry, University of Bristol, BS8 1TS, UK.Search for more papers by this authorAbstract
In this mini review, we strive to highlight the opportunities that exist for the use of aniline oligomeric species in functional materials by reviewing the current state-of-the-art of the various synthetic strategies, as well as the growing number of publications where more complex block-like architectures have been shown. Areas for further investigation and possible future development are highlighted as well.
References
- 1
H. Letheby,
J. Chem. Soc.
1862,
15,
161.
10.1039/JS8621500161 Google Scholar
- 2
A. G. Green,
A. E. Woodhead,
J. Chem. Soc. Trans
1910,
97,
2388.
10.1039/CT9109702388 Google Scholar
- 3 A. G. Green, A. E. Woodhead, J. Chem. Soc. Trans 1912, 101, 1117.
- 4 R. McNeill, D. E. Weiss, J. H. Wardlaw, R. Siudak, Aust. J. Chem. 1963, 16, 1056.
- 5 B. A. Bolto, D. E. Weiss, Aust. J. Chem. 1963, 16, 1076.
- 6 B. A. Bolto, R. McNeill, D. E. Weiss, Aust. J. Chem. 1963, 16, 1090.
- 7 J. McGinnes, P. Corry, P. Proctor, Science 1974, 183, 853.
- 8 H. Shirakawa, E. J. Lewis, A. G. MacDiarmid, C. K. Chiang, A. J. Heeger, J. Chem. Soc. Chem. Comm. 1977, 578.
- 9See also the recent special issue:
Macromol. Rapid Commun.
2007,
28,
1665 (Special Issue: 30 Years of Conducting Polymers).
10.1002/marc.200790034 Google Scholar
- 10 T. A. Skotheim, R. L. Elsenbaumer, J. R. Reynolds, “ Handbook of Conducting Polymers,” 2nd Ed., Marcel Dekker, Inc., 1998.
- 11 R. H. Friend, R. W. Gymer, A. B. Holmes, J. H. Burroughes, R. N. Marks, C. Taliani, D. D. C. Bradley, D. A. Dos Santos, J. L. Bredas, M. Logdlund, W. R. Salaneck, Nature 1999, 397, 121.
- 12 A. G. MacDiarmid, Synth. Met. 1997, 84, 27.
- 13 R. H. Baughman, Science 2005, 308, 63.
- 14 N. Gospodinova, L. Terlemezyan, Prog. Polym. Sci. 1998, 23, 1443.
- 15 E. T. Kang, K. G. Neoh, K. L. Tan, Prog. Polym. Sci. 1998, 23, 277.
- 16 N. K. Guimard, N. Gomez, C. E. Schmidt, Prog. Polym. Sci. 2007, 32, 876.
- 17 H. Sirringhaus, P. J. Brown, R. H. Friend, M. M. Nielsen, K. Bechgaard, B. M. W. Langeveld-Voss, A. J. H. Spiering, R. A. J. Janssen, E. W. Meijer, P. Herwig, D. M. de Leeuw, Nature 1999, 401, 685.
- 18 G. M. Wang, J. Swensen, D. Moses, A. J. Heeger, J. Appl. Phys. 2003, 93, 6137.
- 19 A. Tsumura, H. Koezuka, T. Ando, Appl. Phys. Lett. 1986, 49, 1210.
- 20 R. S. Kohlman, A. Zibold, D. B. Tanner, G. G. Ihas, T. Ishiguro, Y. G. Min, A. G. MacDiarmid, A. J. Epstein, Phys. Rev. Lett. 1997, 78, 3915.
- 21 Y. N. Xia, J. M. Wiesinger, A. G. MacDiarmid, A. J. Epstein, Chem. Mater. 1995, 7, 443.
- 22 Y. N. Xia, A. G. MacDiarmid, A. J. Epstein, Macromolecules 1994, 27, 7212.
- 23 S. M. Long, K. R. Brenneman, A. Saprigin, R. S. Kohlman, A. J. Epstein, M. Angelopoulos, S. L. Buchwalter, A. Rossi, W. Zheng, A. G. MacDiarmid, Synth. Met 1997, 84, 809.
- 24 J. Y. Shimano, A. G. MacDiarmid, Synth. Met. 2001, 123, 251.
- 25 R. S. Kohlman, A. Zibold, D. B. Tanner, G. G. Ihas, T. Ishiguro, Y. G. Min, A. G. MacDiarmid, A. J. Epstein, Phys. Rev. Lett. 1997, 78, 3915.
- 26 K. Lee, S. Cho, S. H. Park, A. J. Heeger, C. W. Lee, S. H. Lee, Nature 2006, 441, 65.
- 27
K. Mullen,
G. Wegner,
“ Electronic Materials: The Oligomer Approach”,
Wiley,
1998.
10.1002/9783527603220 Google Scholar
- 28 F. J. M. Hoeben, P. Jonkheijm, E. W. Meijer, A. Schenning, Chem. Rev. 2005, 105, 1491.
- 29 A. G. MacDiarmid, Y. Zhou, J. Feng, Synth. Met. 1999, 100, 131.
- 30 J. Gierschner, J. Cornil, H. J. Egelhaaf, Adv. Mater. 2007, 19, 173.
- 31 T. Canteenwala, S. V. Patil, M. Haldar, P. A. Padmawar, S. Verma, L. Y. Chiang, J. Macromol. Sci., Pure Appl. Chem. 2003, A40, 1263.
- 32 A. Schenning, E. W. Meijer, Chem. Commun. 2005, 3245.
- 33 F. J. M. Hoeben, P. Jonkheijm, E. W. Meijer, A. Schenning, Chem. Rev. 2005, 105, 1491.
- 34 A. C. Grimsdale, K. Müllen, Angew. Chem. Int. Ed. 2005, 44, 5592.
- 35 F. Wurthner, Chem. Commun. 2004, 1564.
- 36
J. Kromer,
I. Rios-Carreras,
G. Fuhrmann,
C. Musch,
M. Wunderlin,
T. Debaerdemaeker,
E. Mena-Osteritz,
P. Bauerle,
Angew. Chem. Int. Ed.
2000,
39,
3481.
10.1002/1521-3773(20001002)39:19<3481::AID-ANIE3481>3.0.CO;2-O CAS PubMed Web of Science® Google Scholar
- 37 P. Leclere, M. Surin, P. Viville, R. Lazzaroni, A. F. M. Kilbinger, O. Henze, W. J. Feast, M. Cavallini, F. Biscarini, A. Schenning, E. W. Meijer, Chem. Mater. 2004, 16, 4452.
- 38 L. Groenedaal, E. W. Meijer, J. A. J. M. Vekemans, “ Electronic Materials: The Oligomer Approach”, K. Müllen, G. Wegner, Eds., Wiley-VCH, Weinheim 1998, p. 237.
- 39 J. L. Sessler, S. Camiolo, P. A. Gale, Coord. Chem. Rev. 2003, 240, 17.
- 40 J. L. Sessler, G. Berthon-Gelloz, P. A. Gale, S. Camiolo, E. V. Anslyn, P. Anzenbacher, H. Furuta, G. J. Kirkovits, V. M. Lynch, H. Maeda, P. Morosini, M. Scherer, J. Shriver, R. S. Zimmerman, Polyhedron 2003, 22, 2963.
- 41 A. G. MacDiarmid, Y. Zhou, J. Feng, Synth. Met. 1999, 100, 131.
- 42 J. G. Masters, Y. Sun, A. G. MacDiarmid, A. J. Epstein, Synth. Met. 1991, 41, 715.
- 43 J. Libert, J. Cornil, D. A. dosSantos, J. L. Bredas, Phys. Rev. B 1997, 56, 8638.
- 44 O. Kwon, M. L. McKee, J. Phys. Chem. B 2000, 104, 1686.
- 45 S. Stafström, J. L. Brédas, A. J. Epstein, H. S. Woo, D. B. Tanner, W. S. Huang, A. G. MacDiarmid, Phys. Rev. Lett. 1987, 59, 1464.
- 46 J. E. de Albuquerque, L. H. C. Mattoso, R. M. Faria, J. G. Masters, A. G. MacDiarmid, Synth. Met. 2004, 146, 1.
- 47 A. Pron, P. Rannou, Prog. Polym. Sci. 2002, 27, 135.
- 48
A. J. Heeger,
Synth. Met.
1993,
55,
3471.
10.1016/0379-6779(93)90462-6 Google Scholar
- 49 O. T. Ikkala, T. M. Lindholm, H. Ruohonen, M. Selantaus, K. Vakiparta, Synth. Met. 1995, 69, 135.
- 50 Z. X. Wei, T. Laitinen, B. Smarsly, O. Ikkala, C. F. J. Faul, Angew. Chem. Int. Ed. 2005, 44, 751.
- 51 R. Willstätter, C. Moore, Chem. Ber. 1907, 40.
- 52 W. J. Zhang, J. Feng, A. G. MacDiarmid, A. J. Epstein, Synth. Met. 1997, 84, 119.
- 53 Y. Wei, C. C. Yang, T. Z. Ding, Tetrahedron Lett. 1996, 37, 731.
- 54
J. B. Gao,
K. Li,
W. J. Zhang,
C. Wang,
Z. W. Wu,
Y. P. Ji,
Y. Zhou,
M. Shibata,
R. Yosomiya,
Macromol. Rapid Commun.
1999,
20,
560–
563.
10.1002/(SICI)1521-3927(19991001)20:10<560::AID-MARC560>3.0.CO;2-A CAS Web of Science® Google Scholar
- 55 E. Rebourt, J. A. Joule, A. P. Monkman, Synth. Met. 1997, 84, 65.
- 56 I. Kulszewicz-Bajer, I. Rozalska, M. Kurylek, New J. Chem. 2004, 28, 669.
- 57
J. Honzl,
M. Tlustakova,
J. Poly. Sci. Part C.
1968,
22,
451.
10.1002/polc.5070220137 Google Scholar
- 58 F. L. Lu, F. Wudl, M. Nowak, A. J. Heeger, J. Am. Chem. Soc. 1986, 108, 8311.
- 59 W. Wang, A. G. MacDiarmid, Synth. Met. 2002, 129, 199.
- 60 R. A. Singer, J. P. Sadighi, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 213.
- 61 J. P. Sadighi, R. A. Singer, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 4960.
- 62 J. Anand, S. Palaniappan, D. N. Sathyanarayana, Prog. Polym. Sci. 1998, 23, 993.
- 63 R. Anandakathir, T. Canteenwala, H. L. Wang, L. Y. Chiang, J. Macromol. Sci., Pure Appl. Chem. 2006, 43, 1945.
- 64 D. M. Chao, X. B. Ma, Q. H. Liu, X. F. Lu, J. Y. Chen, L. F. Wang, W. J. Zhang, Y. Wei, Eur. Polym. J. 2006, 42, 3078.
- 65 L. Chen, Y. H. Yu, H. P. Mao, X. F. Lu, L. Yao, W. J. Zhang, Y. Wei, Polymer 2005, 46, 2825.
- 66 D. H. Han, C. Y. Pan, Polymer 2006, 47, 6956.
- 67 L. Y. Wang, C. C. Chu, C. F. Yeh, T. I. Ho, S. P. Rwei, Synth. Met. 2003, 135, 111.
- 68 Y. Guo, A. Mylonakis, Z. T. Zhang, P. I. Lelkes, K. Levon, S. X. Li, Q. W. Feng, Y. Wei, Macromolecules 2007, 40, 2721.
- 69 H. F. Wang, P. Guo, Y. C. Han, Macromol. Rapid Commun. 2006, 27, 63.
- 70 B. Dufour, P. Rannou, J. P. Travers, A. Pron, M. Zagorska, G. Korc, I. Kulszewicz-Bajer, S. Quillard, S. Lefrant, Macromolecules 2002, 35, 6112.
- 71 K. Buga, A. Majkowska, R. Pokrop, M. Zagorska, D. Djurado, A. Pron, J. L. Oddou, S. Lefrant, Chem. Mater. 2005, 17, 5754.
- 72 K. Buga, R. Pokrop, A. Majkowska, M. Zagorska, J. Planes, F. Genoud, A. Pron, J. Mater. Chem. 2006, 16, 2150.
- 73 T. Canteenwala, V. Anantharaj, S. V. Patil, M. Halder, L. Y. Chiang, J. Macromol. Sci., Pure Appl. Chem. 2002, A39, 1069.
- 74 T. Canteenwala, S. V. Patil, M. Haldar, P. A. Padmawar, S. Verma, L. Y. Chiang, J. Macromol. Sci., Pure Appl. Chem. 2003, A40, 1263.
- 75 C. Querner, P. Reiss, J. Bleuse, A. Pron, J. Am. Chem. Soc. 2004, 126, 11574.
- 76 C. Querner, P. Reiss, M. Zagorska, O. Renault, R. Payerne, F. Genoud, P. Rannou, A. Pron, J. Mater. Chem. 2005, 15, 554.
- 77 L. W. Shacklette, J. F. Wolf, S. Gould, R. H. Baughman, J. Chem. Phys. 1988, 88, 3955.
- 78 M. Evain, S. Quillard, B. Corraze, W. Wang, A. G. MacDiarmid, Acta Cryst. 2002, E58, o343.
- 79 S. Quillard, B. Corraze, M. Poncet, J. Y. Mevellec, J. P. Buisson, M. Evain, W. Wang, A. G. MacDiarmid, Synth. Met. 2003, 137, 921.
- 80 M. Poncet, B. Corraze, S. Quillard, W. Wang, A. G. MacDiarmid, Thin Solid Films 2004, 458, 32.
- 81 Y. C. Zhou, J. X. Geng, G. Li, E. L. Zhou, L. Chen, W. J. Zhang, J. Polym. Sci., Part B: Polym. Phys. 2006, 44, 764.
- 82 I. Kulszewicz-Bajer, I. Rozalska, M. Kurylek, New J. Chem. 2004, 28, 669.
- 83 A. G. MacDiarmid, Synth. Met. 1997, 84, 27.
- 84 K. Buga, A. Majkowska, R. Pokrop, M. Zagorska, D. Djurado, A. Pron, J. L. Oddou, S. Lefrant, Chem. Mater. 2005, 17, 5754.
- 85 S. Quillard, B. Corraze, M. Poncet, J. Y. Mevellec, J. P. Buisson, M. Evain, W. Wang, A. G. MacDiarmid, Synth. Met. 2003, 137, 921.
- 86 J. Feng, A. G. MacDiarmid, Synth. Met. 1999, 102, 1304.
- 87 R. Payerne, P. Rannou, D. Djurado, F. Genoud, J. P. Travers, Synth. Met. 2005, 152, 193.
- 88 H. S. Nalwa, J. Mater. Sci. 1991, 26, 1683.
- 89 C. C. Chu, C. F. Yeh, L. Y. Wang, T. I. Ho, S. P. Rwei, Synth. Met. 2003, 135, 109.
- 90 K. Z. Zhu, L. X. Wang, X. B. Jing, F. S. Wang, Macromolecules 2001, 34, 8453.
- 91 L. Groenedaal, E. W. Meijer, J. A. J. M. Vekemans, “ Electronic Materials: The Oligomer Approach”, K. Müllen, G. Wegner, Eds., Wiley-VCH, Weinheim 1998, p. 236.
