Citation: Han Ting, Cathy K. W. Jim, Jacky W. Y. Lam, Tang Ben Zhong. Polyynes with Aggregation-Induced Emission Characteristics: Synthesis and Their Photonic Properties[J]. Acta Chimica Sinica, ;2016, 74(11): 877-884. doi: 10.6023/A16070348 shu

Polyynes with Aggregation-Induced Emission Characteristics: Synthesis and Their Photonic Properties

Han Ting ^a,b,† ,
Cathy K. W. Jim ^a,b,† ,
Jacky W. Y. Lam ^a,b,*,, ,
Tang Ben Zhong ^a,b,*,,

a.
Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction, Institute for Advanced Study, Institute of Molecular Functional Materials, Division of Biomedical Engineering, Division of Life Science and State Key Laboratory of Molecular Neuroscience, The Hong Kong University of Science & Technology, Clear Water Bay, Kowloon, Hong Kong, China
b.
HKUST-Shenzhen Research Institute, No. 9 Yuexing 1st RD, South Area, Hi-tech Park, Nanshan, Shenzhen 518057, China

Corresponding author: Jacky W. Y. Lam, chjacky@ust.hk Tang Ben Zhong, tangbenz@ust.hk

^†

Received Date: 16 July 2016

Fund Project: National Basic Research Program of China 973 Programthe National Natural Science Foundation of China 21490570and the Innovation and Technology Commission ITC-CNERC14S01the Research Grants Council of Hong Kong 16305014the University Grants Committee of Hong Kong AoE/P-03/08the Research Grants Council of Hong Kong 16303815B.Z.T. thanks the support of the Guangdong Innovative Research Team Program 201101C0105067115National Basic Research Program of China 2013CB834701the National Natural Science Foundation of China 21490574the Research Grants Council of Hong Kong 604913National Basic Research Program of China 2013CB834702

Figures(11)

Tetraphenylethene-containing diacetylenes are synthesized and their homopolymerizations are catalyzed by CuCl in o-dichlorobenzene, furnishing linear polyynes in high isolated yields. All polymers possess good solubility in common organic solvents and enjoy high thermal stability. Whereas they are practically non-emissive when molecularly dissolved in good solvents, they become highly emissive when aggregated as nanoparticle suspensions in poor solvents or fabricated into thin films in the solid state, demonstrating a novel phenomenon of aggregation-induced emission. The polymers are highly transparent, allowing almost all light in the entire visible spectral region to transmit through. Thin films of the polymers show high refractive indices (n=1.7787~1.6543) in the wavelength region of 400~1700 nm and very low chromatic aberrations (D'=0.0003). Their n values can be modulated and their thin films can be crosslinked by UV irradiation, generating fluorescent patterns with high resolutions.
- linear polyynes,
- aggregation-induced emission,
- tetraphenylethene,
- refractive index
1. [1]
  Cheuk, K. K. L.; Li, B. S.; Tang, B. Z. In Encyclopedia of Nanoscience and Nanotechnology, Vol. 8, Ed.:Nalwa, H. S., American Scientific Publishers, California, 2004, pp. 703~713; (b) Lam, J. W. Y.; Tang, B. Z. J. Polym. Sci. Part A:Polym. Chem. 2003, 41, 2607; (c) Cheuk, K. K. L.; Li, B. S.; Tang, B. Z. Curr. Trends Polym. Sci. 2002, 7, 41. (d) Tang, B. Z. Polym. News 2001, 26, 262; (e) Li, Z.; Dong, Y. Q.; Qin, A. J.; Lam, J. W. Y.; Dong, Y. P.; Yuan, W. Z.; Sun, J. Z.; Hua, J. L.; Wong, K. S.; Tang, B. Z. Macromolecules 2006, 39, 467.
2. [2]
  Liu, J. Z.; Lam, J. W. Y.; Tang, B. Z. Chem. Rev. 2009, 109, 5799; (b) Zhou, L.; Jiang, H. F.; Huang, J. M.; Tang, J. Y. Chinese J. Org. Chem. 2006, 26, 1. (周磊, 江焕峰, 黄精美, 唐金玉, 有机化学, 2006, 26, 1.); (c) Hӓuβler, M.; Lam, J. W. Y.; Qin, A.; Tse, K. K. C.; Li, M. K. S.; Liu, J.; Jim, C. K. W.; Gao, P.; Tang, B. Z. Chem. Commun. 2007, 2584; (d) Qin, A.; Lam, J. W. Y.; Dong, H.; Lu, W.; Jim, C. K. W.; Dong, Y. Q.; Hӓuβler, M.; Sung, H. H. Y.; Williams, I. D.; Wong, G. K. L.; Tang, B. Z. Macromolecules 2007, 40, 4879; (e) Dong, H.; Zheng, R.; Lam, J. W. Y.; Hӓuβler, M.; Tang, B. Z. Macromolecules 2005, 38, 6382; (f) Jim, C. K. W.; Qin, A.; Lam, J. W. Y.; Hӓuβler, M.; Liu, J.; Yuen, M. M. F.; Kim, J. K.; Ng, K. A.; Tang, B. Z. Macromolecules 2009, 42, 4099.
3. [3]
  Jakubiak, R.; Collison, C. J.; Wan, W. C.; Rothberg, L. J.; Hsieh, B. R. J. Phys. Chem. A 1999, 103, 2394.
4. [4]
  Luo, J.; Xie, Z.; Lam, J. W. Y.; Cheng, L.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhao, X.; Liu, Q.; Zhu, D.; Tang, B. Z. Chem. Commun. 2001, 1740.
5. [5]
  Qian, L. J.; Tong, B.; Zhi, J. G.; Yang, F.; Shen, J. B.; Shi, J. B.; Dong, Y. P. Acta Chim. Sinica 2008, 66, 1134. (钱立军, 佟斌, 支俊格, 杨帆, 申进波, 石建兵, 董宇平, 化学学报, 2008, 66, 1134.); (b) Xun, Z. Q.; Tang, H. Y.; Zeng, Y.; Chen, J. P.; Yu, T. J.; Zhang, X. H.; Li, Y. Acta Chim. Sinica 2015, 73, 819. (寻知庆, 唐海云, 曾毅, 陈金平, 于天君, 张小辉, 李嫕, 化学学报, 2015, 73, 819.); (c) Mei, J.; Leung, N. L. C.; Kwok, R. T. K.; Lam, J. W. Y.; Tang, B. Z. Chem. Rev. 2015, 115, 11718; (d) Zhang, Y. H.; Kong, L. W.; Shi, J. B.; Tong, B.; Zhi, J. G.; Feng, X.; Dong, Y. P. Chin. J. Chem. 2015, 33, 701.
6. [6]
  Hu, R. R.; Leung, N. L. C.; Tang, B. Z. Chem. Soc. Rev. 2014, 43, 4494; (b) Wu, W. B.; Tang, R. L.; Li, Q. Q.; Li, Z. Chem. Soc. Rev. 2015, 44, 3997; (c) Hu, R. R.; Li, W. Z.; Tang, B. Z. Macromol. Chem. Phys. 2016, 217, 213.
7. [7]
  Qin, A.; Lam, J. W. Y.; Tang, L.; Jim, C. K. W.; Zhao, H.; Sun, J.; Tang, B. Z. Macromolecules 2009, 42, 1421; (b) Qin, A.; Tang, L.; Lam, J. W. Y.; Jim, C. K. W.; Yu, Y.; Zhao, H.; Sun, J.; Tang, B. Z. Adv. Funct. Mater. 2009, 19, 1891.
8. [8]
  Ogawa, T. Prog. Polym. Sci. 1995, 20, 943; (b) Hay, A. S. J. Polym. Sci. Part A:Polym. Chem. 1998, 36, 505; (c) Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem. Int. Ed. 2000, 39, 2633; (d) Bunz, U. H. F. Chem. Rev. 2000, 100, 1605.
9. [9]
  Higashihara, T.; Ueda, M. Macromolecules 2015, 48, 1915; (b) You, N.-H.; Suzuki, Y.; Higashihara, T.; Ando, S.; Ueda, M. Polymer 2009, 50, 789.
10. [10]
  Hӓuβler, M.; Lam, J. W. Y.; Qin, A.; Tse, K. K. C.; Li, M. K. S.; Liu, J.; Jim, C. K. W.; Gao, P.; Tang, B. Z. Chem. Commun. 2007, 2584; (b) Liu, J.-G.; Ueda, M. J. Mater. Chem. 2009, 19, 8907.
11. [11]
  Raman, C. V. Proc. Ind. Acad. Sci. 1950, 31A, 141; (b) Inoue, T.; Okamoto, H.; Osaki, K. Macromolecules 1991, 24, 5670; (c) Inoue, T.; Hwang, E.-J.; Osaki, K. Polymer 1997, 38, 1029.
12. [12]
  Wei, Q.; Pötzsch, R.; Liu, X. L.; Komber, H.; Kiriy, A.; Voit, B.; Will, P.-A.; Lenk, S.; Reineke, S. Adv. Funct. Mater. 2016, 26, 2545. doi: 10.1002/adfm.v26.15
13. [13]
  Yang, C. J.; Jenekhe, S. A. Chem. Mater. 1995, 7, 1276; (b) Yang, C. J.; Jenekhe, S. A. Chem. Mater. 1994, 6, 196; (c) Liu, Y. J.; Lam, J. W. Y.; Tang, B. Z. Natl. Sci. Rev. 2015, 2, 493; (d) Han, T.; Deng, H. Q.; Yu, C. Y. Y.; Gui, C.; Song, Z. G.; Kowk, R. T. K.; Lam, J. W. Y.; Tang, B. Z. Polym. Chem. 2016, 7, 2501.
14. [14]
  Chu, J. B.; Huang, S. M.; Zhu, H. B.; Xu, X. B.; Sun, Z.; Chen, Y. W.; Huang, F. Q. J. Non-Cryst. Solids 2008, 354, 5480; (b) Chan, C. Y. K.; Lam, J. W. Y.; Jim, C. K. W.; Sung, H. H. Y.; Williams, I. D.; Tang, B. Z. Macromolecules 2013, 46, 9494.
15. [15]
  Campbell, M.; Sharp, D. N.; Harrison, M. T.; Denning, R. G.; Turberfield, A. J. Nature 2000, 404, 53; (b) Li, Z. A.; Jiang, Z. Q.; Ye, S. H.; Jim, C. K. W.; Yu, G.; Liu, Y. Q.; Qin, J. G.; Tang, B. Z.; Li, Z. J. Mater. Chem. 2011, 21, 14663.
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