有机荧光分子2-氰基-3-(3, 4-二甲氧基苯基)-2-丙烯酰胺的可逆压致变色和质子刺激响应性能

doi:10.3866/PKU.WHXB201512083

Acta Phys. -Chim. Sin. ›› 2016, Vol. 32 ›› Issue (2): 589-594.doi: 10.3866/PKU.WHXB201512083

• ARTICLE • Previous Articles

Reversible Piezochromism and Protonation Stimuli-Response of (Z)-2-Cyano-3-(3, 4-dimethoxyphenyl)acrylamide

Gao-Feng BIAN^1,²,Hua HUANG³,Ling-Ling ZHAN¹,Xiao-Jing Lü¹,Feng CAO³,Cheng ZHANG^1,*(),Yu-Jian ZHANG^3,*()

¹ College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. China
² Key Laboratory of Organosilicon Chemistry and Material Technology, Hangzhou Normal University, Hangzhou 310012, P. R. China
³ Department of Materials Chemistry, Huzhou University, Huzhou 313000, Zhejiang Province, P. R. China

Received:2015-10-14 Published:2016-01-30
Contact: Cheng ZHANG,Yu-Jian ZHANG E-mail:czhang@zjut.edu.cn;sciencezyj@foxmail.com
Supported by:
the National Natural Science Foundation of China(51203138, 51273179, 51573165, 51406030);Natural ScienceFoundation of Zhejiang Province, China(LY15E030006, LY15E030002);Natural Science Foundation of Zhejiang University of Technology, China(1401101002408);Natural Science Foundation of Huzhou, China(2014YZ02)

Abstract

Abstract:

A 3-aryl-2-cyano acrylamide derivative (Z)-2-cyano-3-(3, 4-dimethoxy-phenyl)acrylamide (CDMPA) was designed and synthesized, which exhibited piezochromism and acidchromism properties. Under external mechanical force stimuli, CDMPA showed a red-shift of 20 nm in its fluorescence emission and the mechanically induced luminescence color could return to the original state via heating or solvent vapor treatment. Powder X-ray diffraction (XRD) and fluorescence lifetime experiments indicated that the piezochromic luminescence could be attributed to the transformation from the crystalline to the amorphous phase. Additionally, the fluorescence color changed from blue to yellow with a red-shift of 33 nm using the stimulus of protonation. The emission color was recovered upon fuming with dimethyl formamide (DMF) vapor. Infrared (IR) spectra of CDMPA powder and theoretical calculation of the frontier molecular orbitals showed that protonation of the amino moieties in CDMPA had a significant effect on the frontier molecular orbitals and, thus, caused the acidchromism phenomenon. This study provides comprehensive insight into the stimuli-responsive luminescent mechanisms within this type of compound and the reversible switching of emission color may enable discovery of novel applications of CDMPA for detection and sensing devices.

Key words: Acrylamide derivative, Multi-stimuli response, Fluorescence switching, Frontier molecular orbital, Fluorescence lifetime

Gao-Feng BIAN,Hua HUANG,Ling-Ling ZHAN,Xiao-Jing Lü,Feng CAO,Cheng ZHANG,Yu-Jian ZHANG. Reversible Piezochromism and Protonation Stimuli-Response of (Z)-2-Cyano-3-(3, 4-dimethoxyphenyl)acrylamide[J]. Acta Phys. -Chim. Sin. 2016, 32(2), 589-594. doi: 10.3866/PKU.WHXB201512083

References

1	Irie M. ; Fukaminato T. ; Sasaki T. ; Tamai N. ; Kawai T Nature 2002, 420, 759.
2	Lim S. J. ; An B. K. ; Jung S. D. ; Chung M. A. ; Park S. Y Angew. Chem. Int. Edit 2004, 43, 6346.
3	Hirata S. ; Watanabe T Adv. Mater 2006, 18, 2725.
4	Babu, S. S.; Kartha, K. K.; Ajayaghosh, A. J. Phys. Chem. Lett. 2010, 1, 3413. doi: 10.1021/jz101219y
5	Che Y. K. ; Yang X. M. ; Zang L Chem. Commun 2008, 1413
6	Sagara Y. ; Kato T Nat. Chem 2009, 1, 605.
7	Weder C. J Mater. Chem 2011, 21, 8235.
8	Chi Z. G. ; Zhang X. Q. ; Xu B. J. ; Zhou X. ; Ma C. P. ; Zhang Y. ; Liu S.W. ; Xu J. R Chem. Soc. Rev 2012, 41, 3878.
9	Dong Y. J. ; Xu B. ; Zhang J. B. ; Tan X. ; Wang L. J. ; Chen J.L. ; Lv H. G. ; Wen S. P. ; Li B. ; Ye L. ; Zou B. ; Tian W. J Angew. Chem. Int. Edit 2012, 51, 10782.
10	Yoon S. J. ; Chung J.W. ; Gierschner J. ; Kim K. S. ; Choi M.G. ; Kim D. ; Park S. Y. J Am. Chem. Soc 2010, 132, 13675.
11	Suzuki T. ; Shinkai S. ; Sada K Adv. Mater 2006, 18, 1043.
12	Takahashi E. ; Takaya H. ; Naota T. Chem. Eur. J 2010, 16, 4793.
13	Dautel O. ; Robitzer M. ; Lere-Porte J. P. ; Serein-Spirau F. ; Moreau J. J Am. Chem. Soc 2006, 128, 16213.
14	Anthony S. P ChemPlusChem 2012, 77, 518.
15	Sagara Y. ; Kato T Angew. Chem. Int. Edit 2008, 47, 5175.
16	Yamaguchi S. ; Shirasaka T. ; Akiyama S. ; Tamao K. J Am. Chem. Soc 2002, 124, 8816.
17	Zhang Z. L. ; Yao D. D. ; Zhou T. L. ; Zhang H. Y. ; Wang Y Chem. Commun 2011, 47, 7782.
18	Mizoshita N. ; Tani T. ; Inagaki S Adv. Mater 2012, 24, 3350.
19	Kunzelman J. ; Kinami M. ; Crenshaw B. R. ; Protasiewicz J.D. ; Weder C Adv. Mater 2008, 20, 119.
20	Sagara, Y.; Mutai, T.; Yoshikawa, I.; Araki, K. J. Am. Chem. Soc. 2007, 129, 1520. doi: 10.1021/ja0677362
21	Zhao Y. F. ; Gao H. Z. ; Fan Y. ; Zhou T. L. ; Su Z. M. ; Liu Y. ; Wang Y Adv. Mater 2009, 21, 3165.
22	Pucci A. ; Ruggeri G. J Mater. Chem 2011, 21, 8282.
23	Zhang J. B. ; Chen J. L. ; Xu B. ; Wang L. J. ; Ma S. Q. ; Dong Y. J. ; Tian W. J Chem. Commun 2013, 49, 3878.
24	Xue P. C. ; Chen P. ; Jia J. H. ; Xu Q. X. ; Sun J. B. ; Yao B.Q. ; Zhang Z. Q. ; Lu R Chem. Commun 2014, 50, 2569.
25	Xue P. C. ; Lu R. ; Jia J. H. ; Takahuji M. ; Ihara H. Chem. Eur. J 2012, 18, 3549.
26	Dou C. D. ; Han L. ; Zhao S. S. ; Zhang H. Y. ; Wang Y J. Phys. Chem. Lett 2011, 2, 666.
27	Varghese S. ; Das S. J Phys. Chem. Lett 2011, 2, 863.
28	Zhang Y. ; Wang K. ; Zhuang G. L. ; Xie Z. Q. ; Zhang C. ; Cao F. ; Pan G. ; Chen H. F. ; Zou B. ; Ma Y. Chem. Eur. J 2015, 21, 2474.
29	Zhang H. Y. ; Zhang Z. L. ; Ye K. Q. ; Zhang J. Y. ; Wang Y Adv. Mater 2006, 18, 2369.
30	Wei R. R. ; Song P. S. ; Tong A. J. J Phys. Chem. C 2013, 117, 3467.
31	Mutai T. ; Satou H. ; Araki K Nat. Mater 2005, 4, 685.
32	Anthony S. P ChemPlusChem 2012, 77, 518.
33	Zhang X. Q. ; Chi Z. G. ; Xu B. J. ; Chen C. J. ; Zhou X. ; Zhang Y. ; Liu S.W. ; Xu J. R. J Mater. Chem 2012, 22, 18505.
34	Ouyang M. ; Yu C. H. ; Zhang Y. J. ; Hu B. ; Lü X. J. ; Sun J.W. ; Zhang C Acta Phys. -Chim. Sin 2012, 28, 2944.
34	欧阳密; 俞春辉; 张玉建; 胡彬; 吕晓静; 孙璟玮; 张诚. 物理化学学报, 2012, 28, 2944.
35	Zhang Y. J. ; Zhuang G. L. ; Ouyang M. ; Hu B. ; Song Q. B. ; Sun J.W. ; Zhang C. ; Gu C. ; Xu Y. X. ; Ma Y. G Dyes Pigments 2013, 98, 486.
36	Song Q. B. ; Wang Y. S. ; Zhang Y. J. ; Sun J.W. ; Zhang C.New J Chem 2015, 39, 659.
37	Li H. Y. ; Zhang X. Q. ; Chi Z. G. ; Xu B. J. ; Zhou W. ; Liu S.W. ; Zhang Y. ; Xu J. R Org. Lett 2011, 13, 556.
38	Zhang Y. J. ; Sun J.W. ; Zhuang G. L. ; Ouyang M. ; Yu Z.W. ; Cao F. ; Pan G. X. ; Tang P. S. ; Zhang C. ; Ma Y. G J. Mater. Chem. C 2014, 2, 195.
39	Bernard, V. Molecular Fluorescence: Principles and Applications; WCH:Weinheim, Germany, 2001; p 54.
40	Yamaguchi S. ; Shirasaka T. ; Akiyama S. ; Tamao K. J Am. Chem. Soc 2002, 124, 8816.
41	Sun H. T. ; Tian X. H. ; Yuan Y. Z. ; Sun J. Y. ; Sun Z. R. ; Zhuo X. L Acta Phys. -Chim. Sin 2011, 27, 1847.
41	孙海涛; 田晓慧; 元以中; 孙金煜; 孙真荣; 卓小玲. 物理化学学报, 2011, 27, 1847.

[1]	Heran Wang, Kai Chen, Shuo Fu, Haoxuan Wang, Jiaxuan Yuan, Xingyi Hu, Wenjuan Xu, Baoxiu Mi. Isomeric Bisbenzophenothiazines: Synthesis, Theoretical Calculations, and Photophysical Properties [J]. Acta Phys. -Chim. Sin., 2024, 40(1): 2303047-.
[2]	Xiang-Hua. ZHAO,Xiao-Sheng. LI,Li. ZHOU,Na-Na. WU,Xing-Kun. YANG,Shun-Dong. YUAN,Dong-Xue. DING,Hui. XU. A Novel Molecule Based on 2, 2'-Dipyridylamine Functionalized 9, 9-Diarylfluorene with Steric Hindance: Design, Synthesis and Electro-Optical Property Research [J]. Acta Phys. -Chim. Sin., 2015, 31(10): 1971-1976.
[3]	YUAN Shu-Wei, LÜ Rong, YU An-Chi. Photoisomerization Kinetics of IR125 and HDITCP in Ionic Liquids with Different Cation Alkyl Chain Lengths [J]. Acta Phys. -Chim. Sin., 2014, 30(5): 987-993.
[4]	ZHENG Tao, LI Pan, XIAO Sheng-Chun, WANG Dan, Lü Jing-Wen, MEN Zhi-Wei. Luminance Properties and Judd-Ofelt Theory Study of Yb³⁺ Sensitization Wideband Er³⁺ Doped Fluorphosphate Glass [J]. Acta Phys. -Chim. Sin., 2011, 27(09): 2095-2100.
[5]	SUN Hai-Tao, TIAN Xiao-Hui, YUAN Yi-Zhong, SUN Jin-Yu, SUN Zhen-Rong, ZHUO Xiao-Ling. Density Functional Theory Study on Vinyl Thiophene Group Conjugated Spirooxazines [J]. Acta Phys. -Chim. Sin., 2011, 27(08): 1847-1853.
[6]	YU Zhen-Qiang, ZHANG Xin, LI Zi-Chen, CHEN Er-Qiang, LAM Jacky W. Y., TANG Ben-Zhong. Fluorescence Behavior of Biphenyl Containing Side-Chain Liquid Crystalline Polyacetylene with Various Lengths of Spacers [J]. Acta Phys. -Chim. Sin., 2010, 26(08): 2281-2285.
[7]	LEI Yong-Lin, HUO Ji-Chuan. Effect of Alkyl Substitution on the Electronic Structure and Spectrum of Rhodamine [J]. Acta Phys. -Chim. Sin., 2010, 26(02): 447-452.
[8]	Xu Si-Chuan;Zhang Hui-Juan;Sun Zhao-Yong;Feng Juan;Ai Xi-Cheng;Zhang Qi-Yuan;Zhang Xing-Kang;Liu Yan-Qin;Han Shi-Tian. Synthesis and Spectroscopy Characteristics of 5-fluorouracil Porphyrin Compounds [J]. Acta Phys. -Chim. Sin., 2001, 17(10): 879-886.
[9]	Yan Zheng-Lin, Wu Shi-Kang. A Study on the Photophysical Behavior of 1,3,5-triaryl-2 Pyrazoline Compound [J]. Acta Phys. -Chim. Sin., 1994, 10(10): 954-958.

Reversible Piezochromism and Protonation Stimuli-Response of (Z)-2-Cyano-3-(3, 4-dimethoxyphenyl)acrylamide

RichHTML

PDF

Like

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 9

Metrics

Recommended 0