Chinese Journal of Organic Chemistry >
Mechanofluorochromic Luminescence, and Al3+ Detection of an Aggregation-Induced Emission-Active Salicylaldehyde-Based Acylhydrazone Derivative
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)
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.
Junhui Jia , Juanjuan Wen . Mechanofluorochromic Luminescence, and Al3+ Detection of an Aggregation-Induced Emission-Active Salicylaldehyde-Based Acylhydrazone Derivative[J]. Chinese Journal of Organic Chemistry, 2021 , 41(4) : 1728 -1733 . DOI: 10.6023/cjoc202010018
| [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. |
/
| 〈 |
|
〉 |
