含席夫碱基的螺噁嗪类光致变色化合物的合成及性质

高等学校化学学报 ›› 2010, Vol. 31 ›› Issue (5): 976.

含席夫碱基的螺噁嗪类光致变色化合物的合成及性质

杨素华^1,2, 庞美丽¹, 郭心富¹, 李晶晶¹, 韩杰¹, 孟继本¹

1. 南开大学化学系, 天津 300071;
2. 赤峰学院化学系, 赤峰 024000

收稿日期:2009-06-02 出版日期:2010-05-10 发布日期:2010-05-10
通讯作者: 庞美丽, 女, 博士, 副教授, 主要从事有机功能化合物研究. E-mail: pangmeili@nankai.edu.cn
基金资助:
国家自然科学基金(批准号: 20602020)资助.

Synthesis and Properties of Novel Photochromic Dyads Based on Spirooxazine and Schiff Base

YANG Su-Hua^1,2, PANG Mei-Li^1*, GUO Xin-Fu¹, LI Jing-Jing¹, HAN Jie¹, MENG Ji-Ben¹

1. Department of Chemsitry, Nankai University, Tianjin 300071, China;
2. Department of Chemsitry, Chifeng College, Chifeng 024000, China

Received:2009-06-02 Online:2010-05-10 Published:2010-05-10
Contact: PANG Mei-Li. E-mail: pangmeili@nankai.edu.cn
Supported by:
国家自然科学基金(批准号: 20602020)资助.

摘要/Abstract

摘要：

设计合成了一系列含席夫碱基的螺噁嗪双功能光致变色材料4a~4d. 通过¹H NMR, ¹³C NMR, IR和HRMS对其结构进行了表征. 新化合物在几种有机溶剂中均表现出了良好的光致变色性. 研究了化合物在几种高分子膜中的光致变色性. 比较了化合物4b的开环体在两种不同溶剂, 即甲醇和二甲亚砜, 以及3种高分子介质, 即聚甲基丙烯酸甲酯(PMMA)、聚乙烯醇缩丁醛(PVB)和聚乙烯醇(PVA)中的消色速率. 研究了化合物在甲醇、二甲亚砜、PMMA及PVB中的消色过程动力学, 根据化合物在溶液中和高分子介质中开环体消色过程的差别, 推测了存在两种动力学解释的原因. 研究结果显示, 化合物4d在PMMA膜中的耐疲劳度良好.

关键词: 螺噁嗪; 席夫碱; 光致变色; 热消色; 动力学

Abstract:

A series of novel photochromic compounds(4a—4d) based on spirooxazine and Schiff base residue were synthesized. Their structures were characterized by ¹H NMR, ¹³C NMR, IR, and HRMS. The compounds were proved by UV testing to have excellent photochromic properties both in organic solutions and polymer films. The compounds(4a—4d) have shorter photoresponsive time and better photosensitivity than parent compound 3. We have also studied the kinetics of the thermal decay process of the representative compound 4b in methanol, DMSO, and several kinds of films, and presumed why there are two kinds of explains about the kinetics of the thermal decay process in the recent years. The representative compound 4d shows a good fatigue resistance. The applications of compounds 4a—4d in photo-fluorescent and photo-magnetic switch area are under investigation.

Key words: Spirooxazine; Schiff base; Photochromism; Thermal decoloration; Kinetics

TrendMD:

杨素华, 庞美丽, 郭心富, 李晶晶, 韩杰, 孟继本. 含席夫碱基的螺噁嗪类光致变色化合物的合成及性质. 高等学校化学学报, 2010, 31(5): 976.

YANG Su-Hua, PANG Mei-Li*, GUO Xin-Fu, LI Jing-Jing, HAN Jie, MENG Ji-Ben. Synthesis and Properties of Novel Photochromic Dyads Based on Spirooxazine and Schiff Base. Chem. J. Chinese Universities, 2010, 31(5): 976.

参考文献

[1]FENG Chang-Gen(冯长根), WANG Jian-Ying(王建营). Chin. J. Org. Chem.(有机化学)[J], 2006, 26(7): 1012—1023
[2]Kopelman R. A., Snyder S. M., Frank N. L.. J. Am. Chem. Soc.[J], 2003, 125(45): 13684—13685
[3]Kurihara M., Hirooka A., Kume S., et al.. J. Am. Chem. Soc.[J], 2002, 124(30): 8800—8801
[4]Stitzel S., Byrne R., Diamond D.. J. Mater. Sci.[J], 2006, 41: 5841—5844
[5]Berkovic G., Krongauz V., Weiss V.. Chem. Rev.[J], 2000, 100(5): 1741—1744
[6]ZHANG Peng(张鹏), PANG Mei-Li(庞美丽), WANG Yong-Mei(王永梅), et al.. Chem. J. Chinese Universities(高等学校化学学报)[J], 2002, 23(8): 1529—1532
[7]Fissi A., Pieroni O., Ruggeri G., et al.. Macromolecules[J], 1995, 28(1): 302—309
[8]LU Zhen(卢珍), FENG Yu-Lin(冯育林), CHEN Zhao-Bin(陈兆斌), et al.. Chem. J. Chinese Universities(高等学校化学学报)[J], 2005, 26(8): 1451—1454
[9]Guo X. F., Zhang D. Q., Zhou Y. C., et al.. J. Org. Chem.[J], 2003, 68(14): 5681—5867
[10]Yuan W. F., Sun L., Tang H. H., et al.. Adv. Mater.[J], 2005, 17(2): 156—160
[11]Nagashima S., Murata M., Nishihara H.. Angew. Chem.[J], 2006, 118: 4404—4407
[12]WANG Zhi-Lin(王志林), YI Zheng-Ping(易争平), LI Tian(李田), et al.. Chem. J. Chinese Universities(高等学校化学学报)[J], 1996, 17(1): 21—23
[13]HUANG Juan(黄娟), CUI Zi-Ning(崔紫宁), LI Ying(李映), et al.. Chin. J. Org. Chem.(有机化学)[J], 2008, 28(4): 598—604
[14]Iskander M. N., Andrews P. R., Winkler D. A., et al.. Eur. J. Med. Chem.[J], 1991, 26(2): 129—136
[15]Jovanovic B. Z., Marinkovic A. D., Assaleh F. H., et al.. J. Mol. Struct.[J], 2005, 744: 411—416
[16]Macdonald S. F., Chechak A. J.. Can. J. Res.[J], 1948, B26: 432—433
[17]Kakishita T., Matsumoto K., Kiyotsukuri T.. J. Heterocycl. Chem.[J], 1992, 29(12): 1709—1715
[18]LIU Ping(刘平), MING Yang-Fu(明阳福), FAN Mei-Gong(樊美公). Sci. China, Ser. B(中国科学, B辑)[J], 1999, 29(4): 327—333
[19]SHEN Kai-Hua(申凯华), LI Xiao-Lian(李晓莲), CUI Dong-Xun(崔东熏). Chem. J. Chinese Universities(高等学校化学学报)[J], 2005, 26(5): 935—938
[20]Wang S., Yu C. Y., Choi M. S., et al.. J. Photochem. Photobiol. A[J], 2007, 192(5): 17—22
[21]Romani A., Chidichimo G., Formoso P., et al.. J. Phys. Chem. B[J], 2002, 106(37): 9490—9495
[22]Yitzchaik S., Ratner J., Krongauz V., et al.. Liq. Cryst.[J], 1990, 8(5): 677—686
[23]LI Qun(李群), BI Dong-Ying(毕东瀛), WEI Xiong(魏雄), et al.. Acta Photonica Sinica(光子学报)[J], 1997, 26(5): 403—407