Citation: Bin Xin, Luo Weijian, Yuan Wangzhang, Zhang Yongming. Clustering-Triggered Emission of Poly (N-hydroxysuccinimide Methacrylate)[J]. Acta Chimica Sinica, ;2016, 74(11): 935-941. doi: 10.6023/A16080423 shu

Clustering-Triggered Emission of Poly (N-hydroxysuccinimide Methacrylate)

1.
School of Chemistry and Chemical Engineering, Shanghai Key Lab of Electrical Insulation and Thermal Aging, Shanghai Jiao Tong University, Shanghai 200240

Corresponding author: Yuan Wangzhang, wzhyuan@sjtu.edu.cn Zhang Yongming, ymzsjtu@gmail.com
Received Date: 20 August 2016

Fund Project: National Natural Science Foundation of China 51473092and the Shanghai Rising-Star Program 15QA1402500

Figures(6)

Nonconventional luminogens without classic aromatic or conjugated structures are attracting increasing interests owing to their fundamental importance and promising applications in diverse areas. Many of them even exhibit unique aggregation-induced emission (AIE) characteristics. The emission mechanism, however, remains under debate. Previously, we proposed the clustering-triggered emission (CTE) mechanism, namely the clustering of nonconventional chromophores and subsequent electron overlap to rationalize the emission behaviors of such luminogens. To further our understanding, herein, we designed and synthesized poly (N-hydroxysuccinimide methacrylate) (PNHSMA) without any aromatic structures, which was obtained by the radical polymerization of N-hydroxysuccinimide methacrylate (NHSMA) monomer in toluene at 65℃ utilizing azobisisobutyronitrile (AIBN) as initiator. And NHSMA was prepared through the elimination between N-hydroxysuccinimide (NHS) and methacryloyl chloride in the presence of triethylamine (Et₃N). It is found that PNHSMA is virtually nonluminescent in dilute solutions (≤0.4 mg·mL^-1) even at 77 K, but gets emissive in concentrated solutions (e.g. 40 mg·mL^-1) with photoluminescence (PL) maxima at 434 and 485 nm at room temperature. Moreover, its solid powders emit intense blue light with multiple PL peaks upon UV irradiation, indicating its AIE nature and the formation of varying emission species. Further PL measurement of PNHSMA in dimethylformide (DMF) and DMF/acetone (good solvent/nonsolvent) mixtures duly verifies its AIE feature. Meanwhile, NHSMA monomer shows similar emission behaviors to those of PNHSMA, demonstrating concentration enhanced emission and AIE characteristics. In light of above results, it is assumed that NHSMA and its polymeric counterpart PNHSMA may share the similar emission mechanism. Single crystal structure of NHSMA reveals the conjugation of imide group and 3D intermolecular interactions of C=O…C=O (n-π, 3.072 Å), C=O…H-C (2.651, 2.642 Å) and C=O…C-H (3.099 Å). The emission of PNHSMA and NHSMA in concentrated solutions and solid states is thus ascribed to the clustering of imide and ester groups, which results in electronic interactions. The overlap of π and lone pair (n) electrons among C=O, N and O units, together with effective intermolecular interactions in the solid powders extend the conjugation and rigidify the molecular conformations, thus leading to boosted emissions. Such CTE mechanism might be well extended to other nonconventional systems and should be inspiring for the rational design of novel luminogens.
- poly (N-hydroxysuccinimide methacrylate),
- aggregation-induced emission,
- nonconventional luminogens,
- clustering-triggered emission,
- electron cloud overlap
1. [1]
  Qiu, F.; Wang, D.; Zhu, Q.; Zhu, L.; Tong, G.; Lu, Y.; Yan, D.; Zhu, X. Biomacromolecules 2014, 15, 1355. (b) Kang, B.; Afifi, M. M.; Austin, L. A.; El-Sayed, M. A. ACS Nano 2013, 7, 7420.
2. [2]
  Tao, Y.; Yang, C.; Qin, J. Chem. Soc. Rev. 2011, 40, 2943. (b) Wang, Q.; Ding, J.; Ma, D.; Cheng, Y.; Wang, L.; Jing, X.; Wang, F. Adv. Funct. Mater. 2009, 19, 84. (c) Zhang, Q.; Zhou, Q.; Cheng, Y.; Wang, L.; Ma, D.; Jing, X.; Wang, F. Adv. Mater. 2004, 16, 432. (d) Yang, J.; Li, L.; Yu, Y.; Ren, Z.; Peng, Q.; Ye, S.; Li, Q.; Li, Z. Mater. Chem. Front. 2017, 1, DOI:10.1039/C6QM00014B.
3. [3]
  Bai, L.; Li, W.; Chen, J.; Bo, F.; Gao, B.; Liu, H.; Li, J.; Wu, Y.; Ba, X. Macromol. Rapid Commun. 2013, 34, 539. (b) Wu, Y. X.; Li, J. B.; Liang, L. H.; Lu, D. Q.; Zhang, J.; Mao, G. J.; Zhou, L. Y.; Zhang, X. B.; Tan, W.; Shen, G. L.; Yu, R. Q. Chem. Commun. 2014, 50, 2040. (c) Shi, H.; Sun, H.; Yang, H.; Liu, S.; Jenkins, G.; Feng, W.; Li, F.; Zhao, Q.; Liu, B.; Huang, W. Adv. Funct. Mater. 2013, 23, 3268. (d) Chen, M.; Yin, M. Prog. Polym. Sci. 2014, 39, 365.
4. [4]
  Song, Z.; Hong, Y.; Kwok, R. T. K.; Lam, J. W. Y.; Liu, B.; Tang, B. Z. J. Mater. Chem. B 2014, 2, 1717. (b) Zhang, W.; Xu, L.; Qin, J.; Yang, C. Macromol. Rapid Commun. 2013, 34, 442. (c) Wang, M.; Zhang, G.; Zhang, D.; Zhu, D.; Tang, B. Z. J. Mater. Chem. 2010, 20, 185.
5. [5]
  Zhao, Y. S.; Xu, J.; Peng, A.; Fu, H.; Ma, Y.; Jiang, L.; Yao, J. Angew. Chem. 2008, 120, 7411. (b) Gu, X.; Yao, J.; Zhang, G.; Yan, Y.; Zhang, C.; Peng, Q.; Liao, Q.; Wu, Y.; Xu, Z.; Zhao, Y.; Fu, H.; Zhang, D. Adv. Funct. Mater. 2012, 22, 4862.
6. [6]
  Wang, K.; Zhang, H.; Chen, S.; Yang, G.; Zhang, J.; Tian, W.; Su, Z.; Wang, Y. Adv. Mater. 2014, 26, 6168. (b) Liu, D.; Duan, Y.-H. Chin. Chem. Lett. 2013, 24, 809. (c) Yuan, W. Z.; Lu, P.; Chen, S.; Lam, J. W. Y.; Wang, Z.; Liu, Y.; Kwok, H. S.; Ma, Y.; Tang, B. Z. Adv. Mater. 2010, 22, 2159. (d) Yuan, W. Z.; Gong, Y.; Chen, S.; Shen, X. Y.; Lam, J. W. Y.; Lu, P.; Lu, Y.; Wang, Z.; Hu, R.; Xie, N.; Kwok, H. S.; Zhang, Y.; Sun, J. Z.; Tang, B. Z. Chem. Mater. 2012, 24, 1518. (e) Ning, Z.; Chen, Z.; Zhang, Q.; Yan, Y.; Qian, S.; Cao, Y.; Tian, H. Adv. Funct. Mater. 2007, 17, 3799. (f) Wang, C.-R.; Gong, Y.-Y.; Yuan, W.-Z.; Zhang, Y.-M. Chin. Chem. Lett. 2016, 27, 1184.
7. [7]
  Huang, T.; Wang, Z.; Qin, A.; Sun, J. Z.; Tang, B. Z. Acta Chim. Sinica 2013, 71, 979(in Chinese). (黄田, 汪昭旸, 秦安军, 孙景志, 唐本忠, 化学学报, 2013, 71, 979.) (b) Zhu, S.; Song, Y.; Shao, J.; Zhao, X.; Yang, B. Angew. Chem., Int. Ed. 2015, 54, 14626. (c) Pastor-Pérez, L.; Chen, Y.; Shen, Z.; Lahoz, A.; Stiriba, S.-E. Macromol. Rapid Commun. 2007, 28, 1404.
8. [8]
  Yu, W.; Wu, Y.; Chen, J.; Duan, X. Y.; Jiang, X.-F.; Qiu, X.; Li, Y. RSC Adv. 2016, 6, 51257. (b) Yu, W.; Wang, Z.; Yang, D.; Ouyang, X.; Qiu, X.; Li, Y. RSC Adv. 2016, 6, 47632.
9. [9]
  Gong, Y. Y.; Tan, Y. Q.; Mei, J.; Zhang, Y. R.; Yuan, W. Z.; Zhang, Y. M.; Sun, J. Z.; Tang, B. Z. Sci. China Chem. 2013, 56, 1178. (b) Zhou, Q.; Cao, B.; Zhu, C.; Xu, S.; Gong, Y.; Yuan, W. Z.; Zhang, Y. Small 2016, 12, DOI:10.1002/smll.201601545.
10. [10]
  Zhu, S.; Zhang, J.; Wang, L.; Song, Y.; Zhang, G.; Wang, H.; Yang, B. Chem. Commun. 2012, 48, 10889. (b) Niu, S.; Yan, H.; Chen, Z.; Li, S.; Xu, P.; Zhi, X. Polym. Chem. 2016, 7, 3747. (c) Wang, H.-X.; Yang, Z.; Liu, Z.-G.; Wan, J.-Y.; Xiao, J.; Zhang, H.-L. Chem. Eur. J. 2016, 22, 8096. (d) Liu, S. G.; Li, N.; Ling, Y.; Kang, B. H.; Geng, S.; Li, N. B.; Luo, H. Q. Langmuir 2016, 32, 1881.
11. [11]
  Crosby, G. A.; Demas, J. N. J. Phys. Chem. 1971, 75, 991. (b) Lee, W. I.; Bae, Y.; Bard, A. J. J. Am. Chem. Soc. 2004, 126, 8358. (c) Cao, L.; Yang, W.; Wang, C.; Fu, S. J. Macromol. Sci. Part A. 2007, 44, 417. (d) Yang, W.; Pan, C.-Y. Macromol. Rapid Commun. 2009, 30, 2096. (e) You, Y. Z.; Yu, Z. Q.; Cui, M. M.; Hong, C. Y. Angew. Chem. Int. Ed. 2010, 49, 1099. (f) Wang, D.; Yu, Z.-Q.; Hong, C.-Y.; You, Y.-Z. Eur. Polym. J. 2013, 49, 4189. (g) Yang, L.; Wang, L.; Cui, C.; Lei, J.; Zhang, J. Chem. Commun. 2016, 52, 6154.
12. [12]
  Lin, Y.; Gao, J.-W.; Liu, H.-W.; Li, Y.-S. Macromolecules 2009, 42, 3237. doi: 10.1021/ma802353f
13. [13]
  Wu, D. C.; Liu, Y.; He, C. B.; Goh, S. H. Macromolecules 2005, 38, 9906. (b) Sun, M.; Hong, C.-Y.; Pan, C.-Y. J. Am. Chem. Soc. 2012, 134, 20581.
14. [14]
  Restani, R. B.; Morgado, P. I.; Ribeiro, M. P.; Correia, I. J.; Aguiar-Ricardo, A.; Bonifácio, V. D. B. Angew. Chem. Int. Ed. 2012, 51, 5162. doi: 10.1002/anie.201200362
15. [15]
  Wang, D.; Imae, T. J. Am. Chem. Soc. 2004, 126, 13204. doi: 10.1021/ja0454992
16. [16]
  Lin, S. Y.; Wu, T. H.; Jao, Y. C.; Liu, C. P.; Lo, L. W.; Yang, C. S. Chem. Eur. J. 2011, 17, 7158. doi: 10.1002/chem.201100620
17. [17]
  Lu, H.; Feng, L.; Li, S.; Zhang, J.; Lu, H.; Feng, S. Macromolecules 2015, 48, 476. doi: 10.1021/ma502352x
18. [18]
  Mei, J.; Leung, N. L. C.; Kwok, R. T. K.; Lam, J. W. Y.; Tang, B. Z. Chem. Rev. 2015, 115, 11718. (b) Hong, Y.; Lam, J. W. Y.; Tang, B. Z. Chem. Soc. Rev. 2011, 40, 5361. (c) Luo, J.; Xie, Z.; Lam, J. W. Y.; Cheng, L.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhan, X.; Liu, Y.; Zhu, D.; Tang, B. Z. Chem. Commun. 2001, 1740. (d) Wang, J.; Mei, J.; Hu, R.; Sun, J. Z.; Qin, A.; Tang, B. Z. J. Am. Chem. Soc. 2012, 134, 9956. (e) Zhao, Z.; He, B.; Tang, B. Z. Chem. Sci. 2015, 6, 5347.
19. [19]
  Li, C.; Tang, X.; Zhang, L.; Li, C.; Liu, Z.; Bo, Z.; Dong, Y. Q.; Tian, Y.-H.; Dong, Y.; Tang, B. Z. Adv. Opt. Mater. 2015, 3, 1184. (b) Zhao, Z.; Chen, T.; Jiang, S.; Liu, Z.; Fang, D.; Dong, Y. Q. J. Mater. Chem. C 2016, 4, 4800. (c) Feng, C.; Wang, K.; Xu, Y.; Liu, L.; Zou, B.; Lu, P. Chem. Commun. 2016, 52, 3836. (d) Yue, B.-L.; Xie, Z.-Q.; Lu, P.; Ma, Y.-G. Sci. Sinica Chim. 2013, 43, 1065(in Chinese). (越柏玲, 解增旗, 路萍, 马於光, 中国科学:化学, 2013, 43, 1065.)
20. [20]
  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(in Chinese). (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.) (b) Xia, Z.-Q.; Shao, A.-D.; Li, Q.; Zhu, S.-Q.; Zhu, W.-H. Acta Chim. Sinica 2016, 74, 351(in Chinese). (夏志清, 邵安东, 李强, 朱世琴, 朱为宏, 化学学报, 2016, 74, 351.) (c) Bian, S.; Ye, J.-H.; Fan, Z.; Zhang, W.-C.; Wang, L.-Y. Chin. J. Org. Chem. 2016, 36, 855(in Chinese). (卞松, 叶家海, 樊政, 张文超, 王乐勇, 有机化学, 2016, 36, 855.)
21. [21]
  Wang, R. B.; Yuan, W. Z.; Zhu, X. Y. Chin. J. Polym. Sci. 2015, 33, 680. doi: 10.1007/s10118-015-1635-x
22. [22]
  Zhao, E.; Lam, J. W. Y.; Meng, L.; Hong, Y.; Deng, H.; Bai, G.; Tang, B. Z. Macromolecules 2014, 48, 64.
23. [23]
  Miao, X.; Liu, T.; Zhang, C.; Geng, X.; Meng, Y.; Li, X. Phys. Chem. Chem. Phys. 2016, 18, 4295. doi: 10.1039/C5CP07134H
24. [24]
  Niu, S.; Yan, H.; Chen, Z.; Yuan, L.; Liu, T.; Liu, C. Macromol. Rapid Commun. 2016, 37, 136. doi: 10.1002/marc.v37.2
25. [25]
  Mao, B.-W.; Jia, M.; Zhang, L.; Cao, S.-K. Polym. Bull. 2014, (12), 157(in Chinese).
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