Stimuli-responsive luminescent coumarin thiazole hybrid dye: Synthesis, aggregation induced emission, thermochromism and DFT study

被引:24
作者
Shreykar, Milind R. [1 ]
Sekar, Nagaiyan [1 ]
机构
[1] Inst Chem Technol, Dyestuff Technol Dept, Bombay 400019, Maharashtra, India
关键词
Coumarin thiazole; RI-ESIPT; Azomethine; AIE; Thermochromism; DFT; NLO; INTRAMOLECULAR PROTON-TRANSFER; SOLID-STATE FLUORESCENCE; PIEZOCHROMIC LUMINESCENCE; MOLECULAR ASSEMBLIES; PHOTOPHYSICAL PROPERTIES; DERIVATIVES; PIGMENT-YELLOW-101; MECHANOCHROMISM; LIQUID; TETRAPHENYLETHYLENE;
D O I
10.1016/j.dyepig.2017.03.028
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Novel coumarin thiazole hybrid dye with azomethine linkage was synthesized. The dye is very sparingly soluble in DMF and insoluble in other solvents. The dye shows 2 fold increase in emission enhancement on aggregation caused at 60% DMF-H2O mixture. Differential thermal analysis revealed a change from one polymorph to the other polymorph at 285 degrees C leading to emission in the red region. Excited State Intramolecular Proton Transfer takes place with thiazole nitrogen atom and not with -N atom of azomethine linkage contrary to Pigment Yellow 101. High color value (K/S = 10.42) and light fastness (rating = 8) properties were found as compared to Pigment Yellow 101. The computed absorption and emission values were found closer to the experimental values. The pigment exhibits higher first and second order hyperpolarizabilities (24 times more alpha(0), 248 times more beta(0) and 756 times more gamma value than urea). (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:121 / 125
页数:5
相关论文
共 59 条
[1]  
[Anonymous], PHYS CHEM PRINCIPLES
[2]   Fac-Alq3 and Mer-Alq3 Nano/Microcrystals with Different Emission and Charge-Transporting Properties [J].
Bi, Hai ;
Zhang, Hongyu ;
Zhang, Yu ;
Gao, Hongze ;
Su, Zhongmin ;
Wang, Yue .
ADVANCED MATERIALS, 2010, 22 (14) :1631-+
[3]   Organic Crystalline Solids Response to Piezo/thermo Stimulus: Donor-Acceptor (D-A) Attached Salicylaldehyde Azine Derivatives [J].
Chen, Xiaotong ;
Wei, Ruirui ;
Xiang, Yu ;
Zhou, Zhaojuan ;
Li, Kai ;
Song, Panshu ;
Tong, Aijun .
JOURNAL OF PHYSICAL CHEMISTRY C, 2011, 115 (29) :14353-14359
[4]   Recent advances in organic mechanofluorochromic materials [J].
Chi, Zhenguo ;
Zhang, Xiqi ;
Xu, Bingjia ;
Zhou, Xie ;
Ma, Chunping ;
Zhang, Yi ;
Liu, Siwei ;
Xu, Jiarui .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (10) :3878-3896
[5]   Force-induced activation of covalent bonds in mechanoresponsive polymeric materials [J].
Davis, Douglas A. ;
Hamilton, Andrew ;
Yang, Jinglei ;
Cremar, Lee D. ;
Van Gough, Dara ;
Potisek, Stephanie L. ;
Ong, Mitchell T. ;
Braun, Paul V. ;
Martinez, Todd J. ;
White, Scott R. ;
Moore, Jeffrey S. ;
Sottos, Nancy R. .
NATURE, 2009, 459 (7243) :68-72
[6]   Highly sensitive determination of low-level water content in organic solvents using novel solvatochromic dyes based on thioxanthone [J].
Ding, Li ;
Zhang, Zhiyun ;
Li, Xin ;
Su, Jianhua .
CHEMICAL COMMUNICATIONS, 2013, 49 (66) :7319-7321
[7]   Piezochromic Luminescence Based on the Molecular Aggregation of 9,10-Bis((E)-2-(pyrid-2-yl)vinyl)anthracene [J].
Dong, Yujie ;
Xu, Bin ;
Zhang, Jibo ;
Tan, Xiao ;
Wang, Lijuan ;
Chen, Jinlong ;
Lv, Hongguang ;
Wen, Shanpeng ;
Li, Bao ;
Ye, Ling ;
Zou, Bo ;
Tian, Wenjing .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (43) :10782-10785
[8]   Molecular mechanism of the solid-state fluorescence behavior of the organic pigment yellow 101 and its derivatives [J].
Dreuw, A ;
Plötner, A ;
Lorenz, L ;
Wachtveitl, J ;
Djanhan, JE ;
Brüning, B ;
Metz, T ;
Bolte, M ;
Schmidt, MU .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (47) :7783-7786
[9]   Twisted D-π-A solid emitters: efficient emission and high contrast mechanochromism [J].
Gong, Yongyang ;
Tan, Yeqiang ;
Liu, Jun ;
Lu, Ping ;
Feng, Cunfang ;
Yuan, Wang Zhang ;
Lu, Yawei ;
Sun, Jing Zhi ;
He, Gufeng ;
Zhang, Yongming .
CHEMICAL COMMUNICATIONS, 2013, 49 (38) :4009-4011
[10]   Reversible and hydrogen bonding-assisted piezochromic luminescence for solid-state tetraaryl-buta-1,3-diene [J].
Han, Ting ;
Zhang, Yijia ;
Feng, Xiao ;
Lin, Zhengguo ;
Tong, Bin ;
Shi, Jianbing ;
Zhi, Junge ;
Dong, Yuping .
CHEMICAL COMMUNICATIONS, 2013, 49 (63) :7049-7051