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Synthesis of Novel Photochromic Spiropyran Compounds and Their Application Study

  • Tan Chunbin ,
  • Zhao Zelin ,
  • Gao Jun ,
  • Lei Jingxin
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  • a. Chemical Engineering Institute of Sichuan University, Chengdu 610065;
    b. The State Key Laboratory of Polymer Materials Engineering, Sichuan University, Chengdu 610065

Received date: 2011-10-11

  Revised date: 2012-01-12

  Online published: 2012-01-31

Abstract

The several kinds of new novel spiropyran (SP) compounds were first designed and synthesized. The structures of these target compounds were characterized by 1H NMR, IR and MS tests. The photochromic properties of target compounds and their influencing factors were studied, and the applications of SP1 on the polymer materials field were initially investigated. The results show that λmax in UV-vis absorption spectra will shift to longer wavelengths as the result of benzopyran ring linked with strong electrowithdrawing groups; the thermal fade rate is slower with N atom linked with flexible long group; SP1 has good fatigue resistance compared with the other kinds of the target compounds. The fading rate of both SP-g-hPMMA and SP-m-PMMA are obviously slower than that of SP1. The tensile strength and elongation at break of SP-g-hPMMA and SP-m-PMMA were almost unchanged compared with that of PMMA. It is expected that SP-g-hPMMA and SP-m-PMMA will be applied in the field of polymer photochromic materials.

Cite this article

Tan Chunbin , Zhao Zelin , Gao Jun , Lei Jingxin . Synthesis of Novel Photochromic Spiropyran Compounds and Their Application Study[J]. Acta Chimica Sinica, 2012 , 70(9) : 1095 -1103 . DOI: 10.6023/A1110111

References

1. Fan, M.-G.; Yao, J.-N.; Tong, Z.-H. Molecular Photochemistry and Function of Materials, Science Press, Beijing, 2009 (in Chinese). (樊美公, 姚建年, 佟振合, 分子光化学与光功能材料学, 科学出版社, 北京, 2009.)  

2 Fan, M.-G. Prog. Chem. 1994, 6, 3 (in Chinese). (樊美公, 化学进展, 1994, 6, 3.)

3 Berkovic, G.; Krongauz, V.; Weiss, V. Chem. Rev. 2000,100, 1741.  

4 Wei, R.-B.; Zhang, D.-W.; Liang, Y.; Liu, B. Chin. J. Org. Chem. 2008, 28, 1366 (in Chinese). (魏荣宝, 张大为, 梁娅, 刘博, 有机化学, 2008, 28,1366.)

5 Pang, M.-L.; Yang, T.-T.; Li, J.-J.; Yang, S.-H.; Lou, Z.-G.; Han, J.; Meng, J.-B. Acta Chim. Sinica 2010, 68, 1895 (in Chinese). (庞美丽, 杨涛涛, 李晶晶, 杨素华, 娄志刚, 韩杰, 孟继本, 化学学报, 2010, 68, 1895.)

6 Illy, H.; Funderburk, L. J. Org. Chem. 1968, 33, 4283.  

7 Wei, Q.; Chen, S.-P.; Pan, R.-Q. Fine Chemicals 2000, 17, 178 (in Chinese). (魏青, 陈三瓶, 潘瑞琪, 精细化工, 2000, 17, 178.)

8 Zhang, W.-Q.; Wang, J.-B.; Zhou, S.-B.; Zhang, R.-X. J. Hunan Univ. Arts Sci. (Nat. Sci. Ed.). 2006, 18, 31 (in Chinese). (张维庆, 王景炳, 周诗彪, 张儒祥, 湖南文理学院学报 (自然科学版), 2006, 18, 31.)

9 Zhong, S.-F. M.S. Thesis, Huazhong Normal University, Wuhan, 2003 (in Chinese). (钟少锋, 硕士论文, 华中师范大学, 武汉, 2003.)  

10 Liu, R.-L. Shaanxi Chemical 1988, 1, 1 (in Chinese). (刘瑞蓝, 陕西化工, 1988, 1, 1.)

11 Wang, Y.-X.; Zhao, Z.-L.; Gao, J. Chem. Res. Appl. 2010,22(5), 600 (in Chinese). (王钰修, 赵泽琳, 高峻, 化学研究与应用, 2010, 22(5),600.)

12 Durr, H.; Ma, Y.; Cortellaro, G. Synthesis 1995, 294.  

13 McCoy, C. P.; Donnellya, L.; Jonesa, D. S.; Gormana, S. P. Tetrahedron Lett. 2007, 48(4), 657.

14 Nakao, R.; Toyokazu, H.; Yasuo, A. Dyes Pigm. 2002, 52,95.  

15 Li, Z.-J.; Tan, Y.-S.; Ma, Y.-M. Chemistry 1991, 10, 41 (in Chinese). (李仲杰, 谭永生, 马引民, 化学通报, 1991, 10, 41.)

16 Liu, P.; Ming, Y.-F.; Yu, J.; Fan, M.-G. Chin. J. Appl. Chem.1999, 16, 14 (in Chinese). (刘平, 明阳福, 俞君, 樊美公, 应用化学, 1999, 16, 14.)

17 Gu, C.; Yao, Z.-G. J. East China Univ. Sci. Technol. 1995,21(5), 576 (in Chinese). (顾超, 姚祖光, 华东理工大学学报, 1995, 21(5), 576.)
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