Design, Synthesis and Characterization of Triarylacrylonitrile Compounds Exhibiting Aggregation-Induced Emission and High Contrast Reversible Mechanochromism

doi:10.6023/cjoc201306017

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (1): 161-169.DOI: 10.6023/cjoc201306017 Previous Articles Next Articles

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具有聚集诱导发光效应及高对比度可逆力致变色三芳基丙烯腈化合物的设计、合成及性能

毛文纲, 陈康, 欧阳密, 孙璟玮, 周永兵, 王永胜, 宋庆宝, 张诚

浙江工业大学化学工程与材料学院绿色化学合成技术国家重点实验室培育基地杭州 310014

收稿日期:2013-06-09 修回日期:2013-08-20 发布日期:2013-09-06
通讯作者: 宋庆宝,张诚 E-mail:qbsong@zjut.edu.cn; czhang@zjut.edu.cn
基金资助:
国家重点基础研究发展计划（973计划，Nos. 2010CB635108，2011CBA00700）；国际科技合作重点项目计划（No. 2012DFA51210）和中国国家自然科学基金（Nos. 51203138，51273179）资助项目.

Design, Synthesis and Characterization of Triarylacrylonitrile Compounds Exhibiting Aggregation-Induced Emission and High Contrast Reversible Mechanochromism

Mao Wengang, Chen Kang, Ouyang Mi, Sun Jingwei, Zhou Yongbing, Wang Yongsheng, Song Qingbao, Zhang Cheng

a State Key Laboratory Breeding Base for Green Chemistry Synthesis Technology, College of Chemical Engineering and Material Science, Zhejiang University of Technology, Hangzhou 310014

Received:2013-06-09 Revised:2013-08-20 Published:2013-09-06
Supported by:
Project supported by the National Key Basic Research Program of China (973 Program, Nos. 2010CB635108, 2011CBA00700), the International Sci & Tech Cooperation Program (No. 2012DFA51210) and the National Natural Science Foundation of China (Nos. 51203138, 51273179).

1. Design, Synthesis and Characterization of Triarylacrylonitrile Compounds Exhibiting Aggregation-Induced Emission and High Contrast Reversible Mechanochromism.PDF(306KB)

Abstract

Two triarylacrylonitrile compounds, (Z)-2,3-bis(4-(diphenylamino)phenyl)-3-phenyl acrylonitrile (2DPA-TPCN) and (Z)-2,3-bis(4'-(diphenylamino)biphenyl-4-yl)-3-phenyl acrylonitrile (2TPA-TPCN) have been designed and synthesized. Characterizations were performed via nuclear magnetic resonance (NMR) and electron ionization-mass spectrometry (EI-MS). Exhibiting aggregation-induced emission (AIE) activity, the obtained 2DPA-TPCN and 2TPA-TPCN hardly have any luminescence in pure THF solution. However, strong luminescences were observed after adding water to the THF solutions (f_w>60%). When 2DPA-TPCN and 2TPA-TPCN were ground, their colors and intensity turned weakly from saffron [fluorescence quantum efficiency (Φ_F)=2.0%] to orange (Φ_F=12.0%) and from jade green (Φ_F=44.6%) to croci (Φ_F=16.8%), respectively. And the change of the color of 2TPA-TPCN could be discriminated at natural light. Moreover, the ground powder returns to original colour by being exposed to solvent vapor or being heated at about 100 ℃ for 2 min. Photoluminescence (PL) spectra of the samples, which were obtained under different conditions (ungrind and grind), showed that the maximum emission wavelength (λ_em) had a significant red-shift as high as 8 and 39 nm after being ground, respectively. The morphological structures of 2DPA-TPCN and 2TPA-TPCN under different aggregative state were observed by scanning electron microscopy (SEM). The results indicate that the damage on the surface morphology, which was caused by external stimuli, could be restored by being exposed to ethanol vapor or heated. The X-ray diffractometry (XRD) measurements show that the dye that was not ground displays indicative of well-defined microcrystalline-like structures and the grinding dye shows amorphous features in this state. These observations further indicate that the optical properties (PL spectra, Φ_F, fluorescence lifetime) of changes originate from the altering molecular packing mode from the high-order to disorder by being ground. The differential scanning calorimetry (DSC) measurements indicate that the grinding samples which have cold crystal peaks are thermodynamical metastable, while the other states are thermodynamical stable. These results further demonstrate that the primary cause of the reversibility of the grind sample might be the thermodynamical metastable. Furthermore, the thermal decomposition temperatures of 2DPA-TPCN and 2TPA-TPCN is 387.6 and 436.4 ℃ by thermogravimetry (TG) measurement, respectively, which indicates that the compounds have very good thermal stability.

Key words: mechanochromism, reversible, fluorescent material, molecular packing, triarylacrylonitrile

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Mao Wengang, Chen Kang, Ouyang Mi, Sun Jingwei, Zhou Yongbing, Wang Yongsheng, Song Qingbao, Zhang Cheng. Design, Synthesis and Characterization of Triarylacrylonitrile Compounds Exhibiting Aggregation-Induced Emission and High Contrast Reversible Mechanochromism[J]. Chin. J. Org. Chem., 2014, 34(1): 161-169.

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具有聚集诱导发光效应及高对比度可逆力致变色三芳基丙烯腈化合物的设计、合成及性能

Design, Synthesis and Characterization of Triarylacrylonitrile Compounds Exhibiting Aggregation-Induced Emission and High Contrast Reversible Mechanochromism

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