Carbazole-Functionalised Poly(1-phenyl-1-alkyne)s: Synthesis, Light Emission, and Fluorescent Photopatterning
Jacky W. Y. Lam A B , Anjun Qin C , Yuping Dong D , Jianzhao Liu A B , Cathy K. W. Jim A B , Yuning Hong A B , Hoi Sing Kwok E and Ben Zhong Tang A B C F
+ Author Affiliations
- Author Affiliations
A Department of Chemistry, Institute for Advanced Study, State Key Laboratory of Molecular Neuroscience and Institute of Molecular Functional Materials, The Hong Kong University of Science & Technology, Clear Water Bay, Kowloon, Hong Kong, P. R. China.
B The Hong Kong University of Science & Technology, Fok Ying Tung Research Institute, Nansha, Guangzhou, P. R. China.
C Department of Polymer Science & Engineering, Institute of Biomedical Macromolecules, Zhejiang University, Hangzhou 310027, P. R. China.
D College of Materials Science & Engineering, Beijing Institute of Technology, Beijing 100081, P. R. China.
E Center for Display Research, HKUST, Clear Water Bay, Kowloon, Hong Kong, P. R. China.
F Corresponding author. Email: tangbenz@ust.hk
Australian Journal of Chemistry 65(9) 1228-1237 https://doi.org/10.1071/CH12116
Submitted: 24 February 2012 Accepted: 14 April 2012 Published: 18 May 2012
Abstract
Carbazole-containing 1-phenyl-1-alkynes with different spacer lengths [C6H5C≡C(CH2)mCar 1(m) (m = 3, 4, 9), Car =9-carbazolyl] were synthesised in high yields by consecutive substitution and coupling reactions of n-chloro-1-alkynes. Polymerisation of the monomers was effected by NbCl5– and WCl6–Ph4Sn catalysts, furnishing soluble polymers P1(m) with high molecular weights in high yields. All the polymers were thermally stable, commencing to lose their weights at high temperatures (≥ 400°C). Photoexcitation of their THF solutions induced strong blue light emissions with high quantum efficiencies up to 92 %. Multilayer electroluminescence devices with configurations of ITO/P1(m)(:PVK)/BCP/Alq3/LiF/Al were constructed, which gave blue light with maximum luminance and external quantum efficiency of 438 cd m–2 and 0.63 %. UV irradiation of a thin film of P1(4) through a mask oxidized and quenched the light emission of the exposed parts, generating a two-dimensional luminescent photopattern.
References
[1] (a) H. Shirakawa, Angew. Chem. Int. Edit. 2001, 40, 2574.| Crossref | GoogleScholarGoogle Scholar |
(b) A. G. MacDiarmid, Angew. Chem. Int. Edit. 2001, 40, 2581.
| Crossref | GoogleScholarGoogle Scholar |
(c) A. J. Heeger, Angew. Chem. Int. Edit. 2001, 40, 2591.
| Crossref | GoogleScholarGoogle Scholar |
[2] (a) J. C. W. Chien, Polyacetylenes 1984 (Academic Press: New York, NY).
(b) Handbook of Conducting Polymers 1986 (Ed. T. A. Skotheim) (Marcel Dekker: New York, NY).
(c) I. V. Krivoshei, V. M. Skorobogatov, Polyacetylenes and Polyarylenes: Synthesis and Conducting Properties 1991 (Gordon and Breach Science: New York, NY).
[3] (a) S. K. Choi, Y. S. Gal, S. H. Jin, H. K. Kim, Chem. Rev. 2000, 100, 1645.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXhvVyktLs%3D&md5=d07f0e07f438a0266644a25386eed8adCAS |
(b) U. H. F. Bunz, Acc. Chem. Res. 2001, 34, 998.
| Crossref | GoogleScholarGoogle Scholar |
(c) M. B. Nielsen, F. Diederich, Chem. Rev. 2005, 105, 1837.
| Crossref | GoogleScholarGoogle Scholar |
(d) W. Zhang, J. S. Moore, Angew. Chem. Int. Edit. 2006, 45, 4416.
| Crossref | GoogleScholarGoogle Scholar |
(e) T. Masuda, J. Polym. Sci. A Polym. Chem. 2007, 45, 165.
| Crossref | GoogleScholarGoogle Scholar |
(f) J. Wu, W. Pisula, K. Mullen, Chem. Rev. 2007, 107, 718.
| Crossref | GoogleScholarGoogle Scholar |
(g) J. G. Rudick, V. Percec, New J. Chem. 2007, 31, 1083.
| Crossref | GoogleScholarGoogle Scholar |
(h) K. Akagi, Polym. Int. 2007, 56, 1192.
| Crossref | GoogleScholarGoogle Scholar |
(i) S. W. Thomas, G. D. Joly, T. Swager, Chem. Rev. 2007, 107, 1339.
| Crossref | GoogleScholarGoogle Scholar |
(j) W. Y. Wong, Macromol. Chem. Phys. 2008, 209, 14.
| Crossref | GoogleScholarGoogle Scholar |
(k) Y. Morisaki, Y. Chujo, Prog. Polym. Sci. 2008, 33, 346.
| Crossref | GoogleScholarGoogle Scholar |
(l) E. Yashima, K. Maeda, Y. Furusho, Acc. Chem. Res. 2008, 41, 1166.
| Crossref | GoogleScholarGoogle Scholar |
[4] (a) J. Liu, J. W. Y. Lam, B. Z. Tang, Chem. Rev. 2009, 109, 5799.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXpvV2gur0%3D&md5=856ea6f8da0a316076cc2e0504d8c630CAS |
(b) J. W. Y. Lam, B. Z. Tang, Acc. Chem. Res. 2005, 38, 745.
| Crossref | GoogleScholarGoogle Scholar |
(c) J. W. Y. Lam, B. Z. Tang, J. Polym. Sci. A Polym. Chem. 2003, 41, 2607.
| Crossref | GoogleScholarGoogle Scholar |
[5] (a) Y. D. Zhang, T. Wada, H. Sasabe, J. Mater. Chem. 1998, 8, 809.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXhvFWqsL0%3D&md5=a3b2e499f7521bf996b2573d75d2c51eCAS |
(b) C. Maertens, C. Detrembleur, P. Dubois, R. Jérôme, Chem. Mater. 1998, 10, 1010.
| Crossref | GoogleScholarGoogle Scholar |
(c) K. D. Belfield, C. Chinna, O. Najjar, Macromolecules 1998, 31, 2918.
| Crossref | GoogleScholarGoogle Scholar |
(d) X. T. Tao, Y. D. Zhang, T. Wada, H. Sasabe, H. Suzuki, T. Watauabe, S. Miyata, Adv. Mater. 1998, 10, 226.
| Crossref | GoogleScholarGoogle Scholar |
[6] (a) S. Dumitrescu, V. Percec, C. I. Simionescu, J. Polym. Sci. Pol. Chem. 1977, 15, 2893.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE1cXhtVGrt7g%3D&md5=75986df92d4a4f8414263458aad53672CAS |
(b) I. Kmínek, V. Cimurová, S. Nespurek, Macromol. Chem. Physic. 1989, 190, 1025.
| Crossref | GoogleScholarGoogle Scholar |
(c) M. Nakano, T. Masuda, T. Higashimura, Polym. Bull. 1995, 34, 191.
| Crossref | GoogleScholarGoogle Scholar |
(d) H. Tachimori, T. Masuda, J. Polym. Sci. A Polym. Chem. 1995, 33, 2079.
| Crossref | GoogleScholarGoogle Scholar |
(e) T. Sata, R. Nomura, T. Wada, H. Sasabe, T. Masuda, J. Polym. Sci. A Polym. Chem. 1998, 36, 2489.
| Crossref | GoogleScholarGoogle Scholar |
(f) J.-W. Park, J.-H. Lee, H.-N. Cho, S.-K. Choi, Macromolecules 1993, 26, 1191.
| Crossref | GoogleScholarGoogle Scholar |
[7] (a) G. Costa, Comprehensive Polymer Science 1989, Vol. 4, Chapter 9 (Pergamon: Oxford).
(b) T. Masuda, T. Higashimura, Silicon-Based Polymer Science 1990, Chapter 35 (American Chemical Society: Washington, D. C.).
[8] P. P. S. Lee, Y. H. Geng, H. S. Kwok, B. Z. Tang, Thin Solid Films 2000, 363, 149.
| Crossref | GoogleScholarGoogle Scholar |
[9] (a) H. Z. Chen, R. S. Xu, Q. H. Sun, J. W. Y. Lam, M. Wang, B. Z. Tang, Polym. Adv. Technol. 2000, 11, 442.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXosVKntbY%3D&md5=6e430fb222e34da256c2dbf48ad2a7b3CAS |
(b) B. Z. Tang, H. Z. Chen, R. S. Xu, J. W. Y. Lam, K. K. L. Cheuk, H. N. C. Wong, M. Wang, Chem. Mater. 2000, 12, 213.
| Crossref | GoogleScholarGoogle Scholar |
[10] J. W. Y. Lam, H. Peng, M. Häußler, R. Zheng, B. Z. Tang, Mol. Cryst. Liq. Cryst. 2004, 415, 43.
| Crossref | GoogleScholarGoogle Scholar |
[11] (a) M. Tabata, T. Sone, Y. Sadahiro, Macromol. Chem. Phys. 1999, 200, 265.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXhtV2ltL8%3D&md5=17b3287a65b316e8b16ebf435625e95fCAS |
(b) J. L. Reddinger, J. R. Reynolds, Adv. Polym. Sci. 1999, 145, 57.
| Crossref | GoogleScholarGoogle Scholar |
(c) T. Masuda, T. Higashimura, Adv. Polym. Sci. 1987, 81, 121.
| Crossref | GoogleScholarGoogle Scholar |
(d) T. Masuda, T. Takahashi, T. Higashimura, Macromolecules 1985, 18, 311.
| Crossref | GoogleScholarGoogle Scholar |
(e) E. J. Ginsburg, C. B. Gorman, R. H. Grubbs, Modern Acetylene Chemistry 1995, Chapter 10, pp. 353–383 (Eds P. J. Stang, F. Diederich) (VCH: New York, NY).
[12] (a) T. Masuda, B. Z. Tang, T. Higashimura, H. Yamaoka, Macromolecules 1985, 18, 2369.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2MXmtFGqs7c%3D&md5=c1abb4e666895fa14d6cc824ee354c93CAS |
(b) T. Masuda, B. Z. Tang, T. Tanaka, T. Higashimura, Macromolecules 1986, 19, 1459.
| Crossref | GoogleScholarGoogle Scholar |
(c) H. Seki, H. B. Z. Tang, A Tanaka, T Masuda, Polymer (Guildf.) 1994, 35, 3456.
| Crossref | GoogleScholarGoogle Scholar |
(d) S. M. Karim, R. Nomura, T. Masuda, J. Polym. Sci. A Polym. Chem. 2001, 39, 3130.
| Crossref | GoogleScholarGoogle Scholar |
[13] (a) Y. Dong, J. W. Y. Lam, H. Peng, K. K. L. Cheuk, H. S. Kwok, B. Z. Tang, Macromolecules 2004, 37, 6408.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXlvFGit7Y%3D&md5=8f82e73416ea622babda62a3e916e5d5CAS |
(b) J. W. Y. Lam, Y. P. Dong, K. K. L. Cheuk, J. D. Luo, Z. L. Xie, H. S. Kwok, Z. S. Mo, B. Z. Tang, Macromolecules 2002, 35, 1229.
| Crossref | GoogleScholarGoogle Scholar |
(c) J. W. Y. Lam, X. Kong, Y. P. Dong, K. K. L. Cheuk, K. Xu, B. Z. Tang, Macromolecules 2000, 33, 5027.
| Crossref | GoogleScholarGoogle Scholar |
(d) X. Kong, B. Z. Tang, Chem. Mater. 1998, 10, 3352.
| Crossref | GoogleScholarGoogle Scholar |
(e) B. Z. Tang, X. Kong, X. Wan, H. Peng, W. Y. Lam, X. Feng, H. S. Kwok, Macromolecules 1998, 31, 2419.
| Crossref | GoogleScholarGoogle Scholar |
[14] (a) Y. M. Huang, J. W. Y. Lam, K. K. L. Cheuk, W. Ge, B. Z. Tang, Macromolecules 1999, 32, 5976.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXltFSrt7s%3D&md5=1cf7f2a4eadd37ba0e6bde4e4e102b18CAS |
(b) Y. M. Huang, W. Ge, J. W. Y. Lam, B. Z. Tang, Appl. Phys. Lett. 1999, 75, 4094.
| Crossref | GoogleScholarGoogle Scholar |
(c) Y. M. Huang, J. W. Y. Lam, K. K. L. Cheuk, W. Ge, B. Z. Tang, Thin Solid Films 2000, 363, 146.
| Crossref | GoogleScholarGoogle Scholar |
(d) Y. M. Huang, W. Ge, J. W. Y. Lam, K. K. L. Cheuk, B. Z. Tang, Mater. Sci. Eng. B 2001, 85, 122.
| Crossref | GoogleScholarGoogle Scholar |
[15] (a) C. H. Ting, C. S. Hsu, Jpn. J. Appl. Phys. 2001, 40, 5342.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXntFWmtb4%3D&md5=ecb51d029e4bd83feb38bb9de386fcb4CAS |
(b) R. G. Sun, T. Masuda, T. Kobayashi, Jpn. J. Appl. Phys. 1996, 35, L1434.
| Crossref | GoogleScholarGoogle Scholar |
(c) K. Tada, R. Hidayat, M. Teraguchi, T. Masuda, K. Yoshino, Jpn. J. Appl. Phys. 1996, 35, L1138.
| Crossref | GoogleScholarGoogle Scholar |
(d) R. G. Sun, Y. Z. Wang, D. K. Wang, Q. B. Zheng, A. J. Epstein, Synth. Met. 2000, 111–112, 403.
| Crossref | GoogleScholarGoogle Scholar |
(e) R. Hidayat, M. Hirohata, K. Tada, M. Teraguchi, T. Masuda, K. Yoshino, Jpn. J. Appl. Phys. 1997, 36, 3740.
| Crossref | GoogleScholarGoogle Scholar |
(f) Q. Zheng, R. Sun, X. Zhang, T. Masuda, T. Kobayashi, Jpn. J. Appl. Phys. 1997, 36, L1508.
| Crossref | GoogleScholarGoogle Scholar |
[16] (a) R. G. Sun, Q. B. Zheng, X. M. Zhang, T. Masuda, T. Kobayashi, Jpn. J. Appl. Phys. 1999, 38, 2017.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXjtValtbY%3D&md5=fcf2e6b6e7b03cb874c19a34b938ed6cCAS |
(b) M. Hirohata, K. Tada, R. Hidayat, T. Masuda, K. Yoshino, Jpn. J. Appl. Phys. 1997, 36, L302.
| Crossref | GoogleScholarGoogle Scholar |
(c) R. G. Sun, T. Masuda, T. Kobayashi, Synth. Met. 1997, 91, 301.
| Crossref | GoogleScholarGoogle Scholar |
(d) R. G. Sun, T. Masuda, T. Kobayashi, Jpn. J. Appl. Phys. 1996, 35, L1673.
| Crossref | GoogleScholarGoogle Scholar |
[17] (a) J. W. Y. Lam, A. Qin, Y. Q. Dong, Y. Hong, C. K. W. Jim, J. Liu, Y. P. Dong, H. S. Kwok, B. Z. Tang, J. Phys. Chem. B 2008, 112, 11227.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXpvVOqu7c%3D&md5=5806e9151b7f5a06cdf4f2a41700daf9CAS |
(b) J. W. Y. Lam, Y. P. Dong, H. S. Kwok, B. Z. Tang, Macromolecules 2006, 39, 6997.
| Crossref | GoogleScholarGoogle Scholar |
(c) J. W. Y. Lam, A. Qin, Y. Dong, L. M. Lai, M. Häussler, Y. Dong, B. Z. Tang, J. Phys. Chem. B 2006, 110, 21613.
| Crossref | GoogleScholarGoogle Scholar |
[18] (a) Y. Yang, Q. Pei, A. J. Heeger, J. Appl. Phys. 1996, 79, 934.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XltFKnsA%3D%3D&md5=26f64d96bbb3977bc9d9b467c0d5445aCAS |
(b) Y. Yang, Q. Pei, A. J. Heeger, Synth. Met. 1996, 78, 263.
| Crossref | GoogleScholarGoogle Scholar |
(c) G. Leising, S. Tasch, F. Meghdadi, L. Athouel, G. Froyer, U. Scherf, Synth. Met. 1996, 81, 185.
| Crossref | GoogleScholarGoogle Scholar |
(d) S.-A. Chen, C.-I. Chao, Synth. Met. 1996, 79, 93.
| Crossref | GoogleScholarGoogle Scholar |
(e) M. Remmers, D. Neher, J. Grüner, R. H. Friend, G. H. Gelinck, J. M. Warman, C. Quattrocchi, D. A. dos Santos, J.-L. Grédas, Macromolecules 1996, 29, 7432.
| Crossref | GoogleScholarGoogle Scholar |
[19] (a) L. C. Palilis, D. G. Lidzey, M. Redeeker, D. D. C. Bradley, M. Inbasekaran, E. P. Woo, W. W. Wu, Synth. Met. 2001, 121, 1729.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXjslKhs7Y%3D&md5=8f276448ea48615bd017aef28ddb9c68CAS |
(b) X. Z. Jiang, S. Liu, H. Ma, A. K. Y. Jen, Appl. Phys. Lett. 2000, 76, 1813.
| Crossref | GoogleScholarGoogle Scholar |
(c) D. Sainova, T. Mitera, H. G. Nothofer, U. Scherf, I. Glowacki, J. Ulanaski, H. Fujikawa, D. Neher, Appl. Phys. Lett. 2000, 76, 1810.
| Crossref | GoogleScholarGoogle Scholar |
(d) J. P. Chen, G. Klaerner, J.-I. Lee, D. Markiewicz, V. Y. Lee, R. D. Miller, J. C. Scott, Synth. Met. 1999, 107, 129.
| Crossref | GoogleScholarGoogle Scholar |
(e) A. W. Grice, D. D. C. Bradley, M. T. Bernius, M. Inbasekaran, W. W. Wu, E. P. Woo, Appl. Phys. Lett. 1998, 73, 629.
| Crossref | GoogleScholarGoogle Scholar |
(f) M. Ranger, D. Rondeau, M. Leclerc, Macromolecules 1997, 30, 7686.
| Crossref | GoogleScholarGoogle Scholar |
(g) Y. Yang, Q. Pei, J. Appl. Phys. 1997, 81, 3294.
| Crossref | GoogleScholarGoogle Scholar |
(h) Q. Pei, Y. Yang, J. Am. Chem. Soc. 1996, 118, 7416.
| Crossref | GoogleScholarGoogle Scholar |
[20] A. Hilberer, H.-J. Brouwer, B.-J. van der Scheer, J. Wildeman, G. Hadziioannou, Macromolecules 1995, 28, 4525.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXlvFajuro%3D&md5=01f09fafe653c746505a7d5ce38031a2CAS |
[21] (a) L. Liao, Y. Pang, Macromolecules 2001, 34, 7300.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXmslamu70%3D&md5=680043278940c517f7a575d1cbdefe7fCAS |
(b) J. A. Osaheni, S. A. Jenekhe, J. Am. Chem. Soc. 1995, 117, 7389.
| Crossref | GoogleScholarGoogle Scholar |
(c) G. A. Crosby, J. N. Demas, J. Phys. Chem. 1971, 75, 991.
| Crossref | GoogleScholarGoogle Scholar |
(d) J. D. Ingle, S. R. Crouch, Spectrochemical Analysis 1998, pp. 52–55 (Prentice Hall: London).
