Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Research Article

Synthesis, Photophysics and Theoretical Calculation of (E)-2-(benzo[d] thiazol-2-yl)-3-(3-methoxyphenyl)acrylonitrile

Author(s): Pei-Chieh Wu and Chih-Hsien Chen*

Volume 17, Issue 9, 2020

Page: [688 - 693] Pages: 6

DOI: 10.2174/1570178617666200207103147

Price: $65

Abstract

In this study, a new type of luminogen with aggregation-induced-emission (AIE) behavior was designed and synthesized. The result of single-crystal X-ray structure showed a planar structure in which the dihedral angle between two aromatic rings is less than 30o. Moreover, two different intermolecular hydrogen bond interactions supported the stability of the crystal structure. After the formation of organic nanoparticles in poor solubility solvent, the emission intensity of the desired product was increased and the enhancement achieved was 14-fold. This new design of luminogen provided further understanding of the AIE mechanism.

Keywords: Aggregation-induced-emission, benzothiazole, cyanovinyl, fluorescence enhancement, organic nanoparticle

Graphical Abstract
[1]
An, B.K.; Kwon, S.K.; Jung, S.D.; Park, S.Y. J. Am. Chem. Soc., 2002, 124(48), 14410-14415.
[http://dx.doi.org/10.1021/ja0269082] [PMID: 12452716]
[2]
Lim, S.J.; An, B.K.; Park, S.Y. Macromolecules, 2005, 38, 6236-6239.
[http://dx.doi.org/10.1021/ma0504163]
[3]
Chen, C.H.; Lee, S.L.; Lim, T.S.; Chen, C.h.; Luh, T.Y. Polym. Chem., 2011, 2, 2850-2856.
[http://dx.doi.org/10.1039/c1py00259g]
[4]
Wang, T.; Zhao, L.; Wu, Q.; Liu, Y.; Chen, Z.J.; Li, X.H. ACS Appl. Mater. Interfaces, 2017, 9, 3400-3410.
[http://dx.doi.org/10.1021/acsami.6b14118] [PMID: 28067489]
[5]
Zheng, M.; Zhang, J.; Zhang, F.; Xu, B.; Tian, W.J.; Xie, Z.G. Chem. Mater., 2016, 28, 8825-8833.
[http://dx.doi.org/10.1021/acs.chemmater.6b04894]
[6]
Lu, H.; Xu, B.; Dong, Y.; Chen, F.; Li, Y.; Li, Z.; He, J.; Li, H.; Tian, W. Langmuir, 2010, 26(9), 6838-6844.
[http://dx.doi.org/10.1021/la904727t] [PMID: 20112939]
[7]
Sandanayaka, A.S.D.; Matsushima, T.; Adachi, C. J. Phys. Chem. C, 2015, 119, 23845-23851.
[http://dx.doi.org/10.1021/acs.jpcc.5b07084]
[8]
He, L.Z.Z.; Mei, J.; Zhang, T.; Lam, J.W.Y.; Shuai, Z.; Dong, Y-Q.; Tang, B-Z. Chem. Mater., 2015, 27, 6601-6607.
[http://dx.doi.org/10.1021/acs.chemmater.5b02280]
[9]
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. Chem. Comm., 2001, 1740-1741.
[10]
Li, Z.; Dong, Y.; Mi, B.; Tang, Y.; Häussler, M.; Tong, H.; Dong, Y.; Lam, J.W.Y.; Ren, Y.; Sung, H.H.Y.; Wong, K-S.; Gao, P.; Williams, I.D.; Kwok, H-S.; Tang, B-Z. J. Phys. Chem. B, 2005, 109(20), 10061-10066.
[http://dx.doi.org/10.1021/jp0503462] [PMID: 16852217]
[11]
Chen, J-W.; Law, C.C.W.; Lam, J.W.Y.; Dong, Y-P.; Lo, S.M.F.; Williams, I.D.; Zhu, D-B.; Tang, B-Z. Chem. Mater., 2003, 15, 1535-1546.
[http://dx.doi.org/10.1021/cm021715z]
[12]
Itami, K.; Ohashi, Y.; Yoshida, J. J. Org. Chem., 2005, 70(7), 2778-2792.
[http://dx.doi.org/10.1021/jo0477401] [PMID: 15787572]
[13]
Wang, Z.; Shao, H.; Ye, J.; Tang, L.; Lu, P. J. Phys. Chem. B, 2005, 109(42), 19627-19633.
[http://dx.doi.org/10.1021/jp053113j] [PMID: 16853538]
[14]
He, J-T.; Xu, B.; Chen, F-P.; Xia, H-J.; Li, K-P.; Ye, L.; Tian, W-J. J. Phys. Chem. C, 2009, 113, 9892-9899.
[http://dx.doi.org/10.1021/jp900205k]
[15]
Liu, Y.; Deng, C.; Tang, L.; Qin, A.; Hu, R.; Sun, J-Z.; Tang, B-Z. J. Am. Chem. Soc., 2011, 133(4), 660-663.
[http://dx.doi.org/10.1021/ja107086y] [PMID: 21171593]
[16]
Yuan, W.Z.; Lu, P.; Chen, S.; Lam, J.W.Y.; Wang, Z.; Liu, Y.; Kwok, H-S.; Ma, Y.; Tang, B-Z. Adv. Mater., 2010, 22(19), 2159-2163.
[http://dx.doi.org/10.1002/adma.200904056] [PMID: 20564253]
[17]
Chen, C-H.; Satyanarayana, K.; Liu, Y-H.; Huang, S-L.; Lim, T-S.; Luh, T-Y. Chemistry, 2015, 21(2), 800-807.
[http://dx.doi.org/10.1002/chem.201403806] [PMID: 25345595]
[18]
Jiang, S.; Qiu, J.; Chen, Y.; Guo, H.; Yang, F. Dyes Pigments, 2018, 159, 533-541.
[http://dx.doi.org/10.1016/j.dyepig.2018.07.018]
[19]
Sych, G.; Simokaitiene, J.; Bezvikonnyi, O.; Tsiko, U.; Volyniuk, D.; Gudeika, D.; Grazulevicius, J.V. J. Phys. Chem. C, 2018, 122, 14827-14837.
[http://dx.doi.org/10.1021/acs.jpcc.8b03895]
[20]
Zhu, L.; Xie, W.; Zhao, L.; Zhang, Y.; Chen, Z. RSC Advances, 2017, 7, 55839-55845.
[http://dx.doi.org/10.1039/C7RA10820F]
[21]
AINeyadi. J. Med. Chem., 2017, 136, 270-282.

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy