基于聚集诱导发光的水杨醛酰腙衍生物的力致荧光变色和Al3+检测性质研究

贾俊辉; 温娟娟

doi:10.6023/cjoc202010018

有机化学 >

2021 , Vol. 41 >Issue 4: 1728 - 1733

DOI: https://doi.org/10.6023/cjoc202010018

研究简报

基于聚集诱导发光的水杨醛酰腙衍生物的力致荧光变色和Al³⁺检测性质研究

贾俊辉 ,
温娟娟

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1 山西师范大学化学与材料科学学院磁性分子与磁信息材料教育部重点实验室临汾 041004

收稿日期: 2020-10-13

修回日期: 2020-11-20

网络出版日期: 2020-12-19

基金资助

国家自然科学基金(21805175); 山西省高等学校科技创新(2020L0239)

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Mechanoﬂuorochromic Luminescence, and Al³⁺ Detection of an Aggregation-Induced Emission-Active Salicylaldehyde-Based Acylhydrazone Derivative

Junhui Jia ,
Juanjuan Wen

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1 Key Laboratory of Magnetic Molecules and Magnetic Information Material, Ministry of Education, College of Chemistry and Material, Shanxi Normal University, Linfen 041004

* Corresponding author. E-mail: jiajunhui@sxnu.edu.cn

Received date: 2020-10-13

Revised date: 2020-11-20

Online published: 2020-12-19

Supported by

National Natural Science Foundation of China(21805175); Scientific and Technological Innovation Programs of Higher Education Institutions in Shanxi(2020L0239)

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摘要

设计合成了一种基于水杨醛的酰腙衍生物(Z)-N'-[4-(二乙基胺基)-2-羟基苯亚甲基]苯甲酰肼(DHBH). 该化合物不仅表现出优良的聚集诱导发光(AIE)性能, 而且表现出可逆的力致荧光变色性能. 粉末X射线衍射和场发射扫描电镜结果表明, 该DHBH在外界压力刺激下发生力致荧光变色性能的原因是其晶态与无定形态之间的相互转化. 此外, DHBH可以选择性地识别铝离子, 并且显示出很好的抗干扰性, 对铝离子的荧光分析检测限为4.01×10^–9 mol/L.

关键词： 力致荧光变色; 聚集诱导发光; 铝离子; 酰腙

本文引用格式

贾俊辉 , 温娟娟 . 基于聚集诱导发光的水杨醛酰腙衍生物的力致荧光变色和Al³⁺检测性质研究[J]. 有机化学, 2021 , 41(4) : 1728 -1733 . DOI: 10.6023/cjoc202010018

Abstract

In this work, a versatile salicylaldehyde-based acylhydrazone compound (Z)-N'-(4-(diethylamino)-2-hydroxy- benzylidene)benzohydrazide (DHBH) has been designed and easily synthesized. And it not only showed aggregation-induced emission (AIE), but also reversible mechanochromic luminescence. The results of powder X-ray diffraction (PXRD) and field emission scanning electron microscopy (FESEM) revealed that the mechano?uorochromic (MFC) mechanism was the transformation between ordered crystalline and amorphous states upon external stimuli. In addition, compound DHBH displayed selective turn-on fluorescence with Al³⁺ and the probe exhibited good response and anti-interference performance. The detection limit for Al³⁺ was calculated to be about 4.01×10^–9 mol/L.

Key words： mechano?uorochromic luminescence; aggregation-induced emission; aluminium ion; acylhydrazone

参考文献

[1]	Li, Q.-Q.; Li, Z. Acc. Chem. Res. 2020, 53(4),962.
[2]	Wang, C.; Li, Z. Mater. Chem. Front. 2017, 1,2174.
[3]	Yang, J.; Li, Z. Chin. J. Org. Chem. 2019, 39,3304. (in Chinese)
[3]	( 杨杰, 李振, 有机化学, 2019, 39,3304.)
[4]	Sagara, Y.; Kato, T. Nat. Chem. 2009, 1,605.
[5]	Yoshii, R.; Suenaga, K.; Tanaka, K.; Chujo, Y. Chem 2015, 21,7231.
[6]	Jia, J.H.; Wu, Y. Dyes Pigm. 2017, 147,537.
[7]	Oda, K.; Hiroto, S.; Shinokubo, H. J. Mater. Chem. C 2017, 5,5310.
[8]	Jia, J.H.; Wu, Y.-Y. Dyes Pigm. 2017, 136,657.
[9]	Jia, J.H.; Zhao, H.X. Tetrahedron Lett. 2019, 60,252.
[10]	Chen, X.T.; Wei, R.-R.; Xiang, Y.; Zhou, Z.J.; Li, K.; Song, P.S.; Tong, A.J. J. Phys. Chem. C 2011, 115,14353.
[11]	Jia, J.H.; Xue, P.C.; Lu, R. Tetrahedron Lett. 2016, 57,2544.
[12]	Jia, J.H.; Zhang, H.J. J. Photochem. Photobiol., 2018, 353,521.
[13]	Butler, T.; Zhuang, M.; Fraser, C.L. J. Phys. Chem. C 2018, 122,19090.
[14]	Gan, K.P.; Yoshio, M.; Kato, T. J. Mater. Chem. C 2016, 4,5073.
[15]	Luo, W.J.; Zhang, Y.R.; Gong, Y.Y.; Zhou, Q.; Zhang, Y.M.; Yuan, W.Z. Chin. Chem. Lett. 2018, 29,1533.
[16]	Santhiya, K.; Sen, S.K.; Natarajan, R.; Shankar, R.; Murugesapandian, B. J. Org. Chem. 2018, 83,10770.
[17]	Huang, L.L.; Liu, J.W.; Liu, L.; Yang, Q.Y.; Ma, Z.Y.; Jia, X.R. Dyes Pigm. 2020, 173,107963.
[18]	Sharber, S.A.; Mann, A.; Shih, K.C.; Mullin, W.J.; Nieh, M.P.; Thomas, S.W. J. Mater. Chem. C 2019, 7,8316.
[19]	Jadhav, T.; Choi, J.M.; Dhokale, B.; Mobin, S.M.; Lee, J.Y.; Misra, R. J. Phys. Chem. C 2016, 120,18487.
[20]	Li, K.; Su, X.; Wang, Y.X.; Tao, F.R.; Cui, Y.Z.; Zhang, H.Y.; Li, T.D. J. Lumin. 2018, 203,50.
[21]	Cui, Y.; Yin, Y.M.; Cao, H.T.; Zhang, M.; Shan, G.G.; Sun, H.Z.; Wu, Y.; Su, Z.M.; Xie, W.F. Dyes Pigm. 2015, 119,62.
[22]	Sun, H.; Sun, W.-H.; Jiang, Y.; Wei, J.-H.; Zhao, Y.; Zhang, R.; Ni, Z.-H. Dyes Pigm. 2020, 173,107938.
[23]	Sagara, Y.; Takahashi, K.; Nakamura, T.; Tamaoki, N. Chem.-Asian J. 2020, 15,478.
[24]	Sagara, Y.; Seki, A.; Kim, Y.; Tamaoki, N. J. Mater. Chem. C 2018, 6,8453.
[25]	Sagara, Y.; Komatsu, T.; Ueno, T.; Hanaoka, K.; Kato, T.; Nagano, T. Adv. Funct. Mater. 2013, 23,5277.
[26]	Mao, W.G.; Chen, K.; Ouyang, M.; Sun, J. W.; Zhou, Y.B.; Wang, Y.S.; Song, Q.B.; Zhang, C. Chin. J. Org. Chem. 2014, 34,161. (in Chinese)
[26]	( 毛文纲, 陈康, 欧阳密, 孙璟玮, 周永兵, 王永胜, 宋庆宝, 张诚, 有机化学, 2014, 34,161.)
[27]	Ma, C.P.; Zhang, X.Q.; Yang, L.T.; Li, Y.; Liu, H.L.; Yang, Y.; Xie, G.Y.; Ou, Y.-C.; Wei, Y. Dyes Pigm. 2017, 136,85.
[28]	Zheng, M.; Zhang, D.T.; Sun, M.X.; Li, Y.P.; Liu, T.L.; Xue, S.F.; Yang, W.J. J. Mater. Chem. C 2014, 2,1913.
[29]	Shi, H.J.; Liu, R.; Zhu, S.Q.; Gong, Q.-Q.; Shi, H.; Zhu, X.L.; Zhu, H.J. J. Fluoresc. 2016, 26,2005.
[30]	Zhao, F.; Chen, Z.; Liu, G.; Fan, C.B.; Pu, S.Z. Tetrahedron Lett. 2018, 59,836.
[31]	Li, A.S.; Liu, Y.J.; Han, L.; Xu, S.P.; Song, C.P.; Geng, Y.J.; Pan, L.Y.; Xu, B.; Tian, W.J.; Zhang, H.Y.; Xu, W.Q.; Cui, H.N. Dyes Pigm. 2019, 161,182.
[32]	Jia, J.H.; Wu, L. Org. Electron. 2020, 76,105466.
[33]	Jia, J.H.; Wu, L. Tetrahedron Lett. 2020, 61,152486.
[34]	Sharma, S.; Dubey, G.; Sran, B.S.; Bharatam, P.V.; Hundal, G. ACS Omega 2019, 4,18520.
[35]	Sahana, A.; Banerjee, A.; Lohar, S.; Banik, A.; Mukhopadhyay, S.K.; Safin, D.A.; Babashkina, M.G.; Bolte, M.; Garcia, Y.; Das, D. Dalton Trans. 2013, 42,18520.
[36]	Sinha, S.; Chowdhury, B.; Ghosh, P. Inorg. Chem. 2016, 55,9212.
[37]	Lee, S.A.; You, G.R.; Choi, Y.W.; Jo, H.Y.; Kim, A.R.; Noh, I.; Kim, S.-J.; Kim, Y.; Kim, C. Dalton Trans. 2014, 43,6650.
[38]	Li, W.; Jia, X.; Guo, Z.B.; Jiang, W.T.; Zhang, P.Z.; Wei, C.; Li, X.L. Chin. J. Org. Chem. 2020, 40,1934. (in Chinese)
[38]	( 李维, 贾旭, 郭振波, 姜文婷, 张平竹, 魏超, 李小六, 有机化学, 2020, 40,1934.)
[39]	He, Y.Q.; Zhao, B.; Kan, W.; Wang, L.Y.; Song, B.; Yin, G.M.; Bi, Y.; Chen, S.W. Chin. J. Org. Chem. 2019, 39,3250. (in Chinese)
[39]	( 何玉倩, 赵冰, 阚伟, 王丽艳, 宋波, 殷广明, 毕野, 陈书文, 有机化学, 2019, 39,3250.)
[40]	Guan, X.L.; Li, Z.F.; Wang, L.; Liu, M.N.; Wang, K.L.; Yang, X.Q.; Li, Y. L.; Lai, S.J. Acta Chim. Sinica 2019, 77,1268. (in Chinese)
[40]	( 关晓琳, 李志飞, 王林, 刘美娜, 王凯龙, 杨学琴, 李亚丽, 胡丽丽, 赵小龙, 来守军, 雷自强, 化学学报, 2019, 77,1268.)
[41]	Qi, F.; Lin, J.J.; Wang, X.Q.; Cui, P.; Yan, H.; Gong, S.W.; Ma, C.L.; Liu, Z.P.; Huang, W. Dalton Trans. 2016, 45,7278.
[42]	Xu, D.F.; Wang, Y.; Li, L.; Zhou, H.K.; Liu, X.L. RSC Adv. 2020, 10,12025.
[43]	Sun, T.; Cheng, D.D.; Chai, Y.S.; Gong, J.; Sun, M.Y.; Zhao, F. Dyes Pigm. 2019, 170,107619.
[44]	Qi, Y.P.; Wang, Y.T.; Yu, Y.J.; Liu, Z.Y.; Zhang, Y.; Du, G.F.; Qi, Y. RSC Adv. 2016, 6,33755.
[45]	Jia, J.H.; Zhao, H.X. New. J. Chem. 2019, 43,2231.
[46]	Xue, P.C.; Ding, J.P.; Shen, Y.B.; Gao, H.Q.; Zhao, J.Y. Dyes Pigm. 2017, 145,12.
[47]	Xue, S.F.; Qiu, X.; Sun, Q.K.; Yang, W.J. J. Mater. Chem. C 2016, 4,1568.
[48]	Liu, X.D.; Li, A.S.; Xu, W.Q.; Ma, Z.Y.; Jia, X.R. Mater. Chem. Front. 2019, 3,620.
[49]	Panda, M.K.; Ravi, N.; Asha, P.; Prakasham, A.P. CrystEngComm 2018, 20,6046.
[50]	Dai, Q.; Zhang, J.Y.; Tan, R.H.; Wang, S.; Li, Y.Q.; Li, Q.; Xiao, S.Z. Mater. Lett. 2016, 164,239.
[51]	Cheng, D.D.; Xu, D.F.; Wang, Y.; Zhou, H.K.; Zhang, Y.H.; Liu, X.L.; Han, A.X.; Zhang, C. Dyes Pigm. 2020, 173,107934.
[52]	Jia, J.H.; Zhao, H.X. Org. Electron. 2019, 73,55.
[53]	Zuo, Z.Y.; Tang, Y.P.; Lei, F.H.; Jin, R. Y.; Yin, P.C.; Li, Y.; Niu, Q.F. Spectrochim. Acta, Part A 2020, 242,118742.
[54]	Berthon, G. Coord. Chem. Rev. 2002, 228,319.

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