Citation: Qiao LI, Zhi-Gang NIU, Yan-Ling LIU, En-Ju WANG. Crystal Structure and Aggregation-induced Emission of an Azine Derivative[J]. Chinese Journal of Structural Chemistry, ;2020, 39(4): 693-697. doi: 10.14102/j.cnki.0254-5861.2011-2464 shu

Crystal Structure and Aggregation-induced Emission of an Azine Derivative

Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry & Chemical Engineering, Hainan Normal University, Haikou 571158, China

Corresponding author: En-Ju WANG, enjuwang@163.com
Received Date: 20 May 2019
Accepted Date: 8 September 2019

Fund Project: the Natural Science Foundation of Hainan Province 20162028the Program for Innovative Research Team in University IRT-16R19

Figures(5)

An AIE-active azine derivative (1) was facilely synthesized by aldehyde-amine condensation of 2-hydroxy-1-naphthaldehyde and 3-methyl-2-benzothiazolinone hydrazone. It crystallizes in the monoclinic space group P2₁/n with a = 8.2176(5), b = 13.1733(7), c =14.5731(8) Å, β = 90.521(5)º, and Z = 4. Compound 1 exhibits aggregation-induced emission characteristics. In dilute solution, it is non-emissive, while strong emission was observed in the aqueous medium as a result of the molecular aggregation in poor solvent. The powder and crystals of 1 also exhibit strong fluorescence. In its crystal lattice, the molecules stack in a face-to-face style, but there is no π-π stacking interaction due to the long distance between adjacent molecules. It is the loose stacking mode that blocks the nonradiative decay channel resulting in its AIE effect.
- aggregation-induced emission,
- crystal structure,
- 2-hydroxy-1-naphthaldehyde,
- azine
1. [1]
  Luo, J.; Xie, Z.; Lam, J. W. Y.; Cheng, L.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhan, X.; Liu, Y.; Zhu, D.; Tang, B. Z. Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole. Chem. Commun. 2001, 18, 1740−1741.
2. [2]
  Chen, B.; Nie, H.; Lu, P.; Zhou, J.; Qin, A.; Qiu, H.; Zhao, Z.; Tang, B. Z. Conjugation versus rotation: good conjugation weakens, the aggregation-induced emission effect of siloles. Chem. Commun. 2014, 50, 4500−4503. doi: 10.1039/c4cc00653d
3. [3]
  Shimizu, M.; Tatsumi, H.; Mochida, K.; Shimono, K.; Hiyama, T. Synthesis, crystal structure, and photophysical properties of (1E,3E,5E)-1,3,4,6-tetraarylhexa-1,3,5-trienes: a new class of fluorophores exhibiting aggregation-induced emission. Chem.-Asian J. 2009, 4, 1289−1297. doi: 10.1002/asia.200900110
4. [4]
  He, J. T.; Xu, B.; Chen, F. P.; Xia, H. J.; Li, K. P.; Ye, L.; Tian, W. J. Aggregation-induced emission in the crystals of 9,10-distyrylanthracene derivatives: the essential role of restricted intramolecular torsion. J. Phys. Chem. C 2009, 113, 9892−9899. doi: 10.1021/jp900205k
5. [5]
  Zheng, Y. S.; Hu, Y. J.; Li, D. M.; Chen, Y. C. Enantiomer analysis of chiral carboxylic acids by AIE molecules bearing optically, pure aminol groups. Talanta 2010, 80, 1470−1474 doi: 10.1016/j.talanta.2009.09.030
6. [6]
  Ding, D.; Li, K.; Liu, B.; Tang, B. Z. Bioprobes based on AIE fluorogens. Acc. Chem. Res. 2013, 46, 2441−2453. doi: 10.1021/ar3003464
7. [7]
  Sanji, T.; Nakamura, M.; Kawamata, S.; Tanaka, M.; Itagaki, S.; Gunji, T. Fluorescence turn-on detection of melamine with aggregation-induced-emission-active tetraphenylethene. Chem.-Eur. J. 2012, 18, 15254−15257. doi: 10.1002/chem.201203081
8. [8]
  Huang, J.; Tang, R.; Zhang, T.; Li, Q.; Yu, G.; Xie, S.; Liu, Y.; Ye, S.; Qin, J.; Li, Z. A new approach to prepare efficient blue AIE emitters for undoped OLEDs. Chem.-Eur. J. 2014, 20, 5317−5326. doi: 10.1002/chem.201303522
9. [9]
  Wang, M.; Zhang, D. Q.; Zhang, G. X.; Zhu, D. B. Fluorescence enhancement upon gelation and thermally-driven fluorescence switches based on tetraphenylsilole-based organic gelators. Chem. Phys. Lett. 2009, 475, 64−67. doi: 10.1016/j.cplett.2009.05.029
10. [10]
  Chen, J.; Law, C. C. W.; Lam, J. W. Y.; Dong, Y.; Lo, S. M. F.; Williams, I. D.; Zhu, D.; Tang, B. Z. Synthesis, light emission, nanoaggregation and restricted intramolecular rotation of 1,1-substituted2,3,4,5-tetraphenylsiloles. Chem. Mater. 2003, 15, 1535−1546. doi: 10.1021/cm021715z
11. [11]
  Yuan, C.; Saito, S.; Camacho, C.; Kowalczyk, T.; Irle, S.; Yamaguchi, S. Hybridization of a flexible cyclooctatetraene core and rigid aceneimide wings for multiluminescent flapping π systems. Chem., -Eur. J. 2014, 20, 2193−2200. doi: 10.1002/chem.201303955
12. [12]
  Chen, J.; Su, W.; Wang, E.; Liu, Y. 1,8-Naphthalimide-based turn-on fluorescent chemosensor for Cu²⁺ and its application in bioimaging. J. Lumin. 2016, 180, 301−305. doi: 10.1016/j.jlumin.2016.08.040
13. [13]
  Su, W.; Yuan, S.; Wang, E. A rhodamine-based fluorescent chemosensor for the detection of Pb²⁺, Hg²⁺ and Cd²⁺. J. Fluoresc. 2017, 27, 1871−1875. doi: 10.1007/s10895-017-2124-0
14. [14]
  Zhang, Z.; Yuan, S.; Wang, E. A dual-target fluorescent probe with response-time dependent selectivity for Cd²⁺ and Cu²⁺. J. Fluoresc. 2018, 28, 1115–1119. doi: 10.1007/s10895-018-2274-8
15. [15]
  Zhang, Z.; Liu, Y.; Wang, E. A highly selective turn-on fluorescent probe for detecting Cu²⁺ in two different sensing mechanisms. Dyes Pigments 2019, 163, 533−537. doi: 10.1016/j.dyepig.2018.12.039
16. [16]
  Han, T.; Hong, Y.; Xie, N.; Chen, S.; Zhao, N.; Zhao, E.; Lam, J. W. Y.; Sung, H. H. Y.; Dong, Y.; Tong, B.; Tang, B. Z. Defect-sensitive crystals based on diaminomaleonitrile-functionalized Schiff base with aggregation-enhanced emission. J. Mater. Chem. C 2013, 1, 7314−7320. doi: 10.1039/c3tc31562b
17. [17]
  Cao, X.; Zeng, X.; Mu, L.; Chen, Y.; Wang, R.; Zhang, Y.; Zhang, J.; Wei, G. Characterization of the aggregation-induced enhanced emission, sensing, and logic gate behavior of 2-(1-hydroxy-2-naphthyl)methylene hydrazine. Sens. Actuators B Chem. 2013, 177, 493−499. doi: 10.1016/j.snb.2012.11.003
18. [18]
  Xiao, H.; Chen, K.; Cui, D.; Jiang, N.; Yin, G.; Wang, J.; Wang, R. Two novel aggregation-induced emission active coumarin-based Schiff bases and their applications in cell imaging. New J. Chem. 2014, 38, 2386−2393. doi: 10.1039/C3NJ01557B
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