Synthesis, theoretical and photophysical studies of mono-alkynylated tetrathienylethene via Sonogashira reaction: A useful tool for enhancement of their aggregation induced emission properties.
Abstract
The tetrathienylethene is firstly synthesized via a novel single step via Stille palladium(0) cross coupling reaction of tetrachloroethene with 2-(tributylstannyl)thiophene. The Sonogashira coupling reaction of bromotetrathienylethene with various alkynes are reported. Especially, their photophysical properties and aggregation induced emission effects of alkynylated tetrathienylethene are enhanced, tunable and characterized.Downloads
References
T. Suzuki, H. Fujii, Y. Yamashita, C. Kabuto, S. Tanaka, M. Ishikawa, T. Hamada, K. Oda, Angew. Chem. Int. Ed., 31(4) (1992) 455-458. https://doi.org/10.1002/anie.199204551
A. Bolzoni, C. Zani, G. Alberti, M. Costa, N. Della Ca', Eur. J. Org. Chem., 2013(33) (2013) 7489-7499. https://doi.org/10.1002/ejoc.201300745
J.J. Liu, J. Yang, J.L. Wang, Z.F. Chang, B. Li, W.T. Song, Z. Zhao, X. Lou, J. Dai, F. Xia, Mater. Chem. Front., 2(6) (2018) 1126-1136. https://doi.org/10.1039/C8QM00008E
J. Song, T. Wu, X. Zhao, Y. Kan, H. Wang, Tetrahedron, 71(12) (2015) 1838-1843. https://doi.org/10.1016/j.tet.2015.02.004
H. Nguyen, T.T.T. Luong, N.B. Nguyen, H.T.H. Le, M. Chi P, L. Van Meervelt, M.T. Do, T.T. Dang, Tetrahedron, 142 (2023) 133539. https://doi.org/10.1016/j.tet.2023.133539
J. Mei, N.L.C. Leung, R.T.K. Kwok, J.W.Y. Lam, B.Z. Tang, Chem. Rev., 115(21) (2015) 11718-11940. https://doi.org/10.1021/acs.chemrev.5b00263
L. Viglianti, N.L.C. Leung, N. Xie, X. Gu, H.H.Y. Sung, Q. Miao, I.D. Williams, E. Licandro, B.Z. Tang, Chem. Sci., 8(4) (2017) 2629-2639. https://doi.org/10.1039/C6SC05192H
C. Shen, Y. Wu, Z. Zhang, E. Li, W. Zhang, X. Xu, W. Wu, H. Tian, W. Zhu, Angew. Chem. Int. Ed., 58(12) (2019) 3784-3789. https://doi.org/10.1002/anie.201811593
K. Yamanaka, M. Fujitsuka, Y. Araki, O. Ito, T. Aoshima, T. Fukushima, T. Miyashi, J. Phys. Chem. A, 108(2) (2004) 250-256. https://doi.org/10.1021/jp036932h
W. Song, J. Zhi, T. Wang, B. Li, S. Ni, Y. Ye, J. Wang, Chem. Asian J., 14(21) (2019) 3875-3882. https://doi.org/10.1002/asia.201901097
L. Sun, Q. Liao, Y. Li, F.E. Hahn, Y. Han, Adv. Opt. Mater., 11(5) (2023) 2202516. https://doi.org/10.1002/adom.202202516
D. Lenoir, Synthesis, 1977(08) (1977) 553-554. https://doi.org/10.1055/s-1977-24469
T. Wu, J. Shi, C. Li, J. Song, L. Xu, H. Wang, Org. Lett., 15(2) (2013) 354-357. https://doi.org/10.1021/ol303300w
E. Fischer, J. Larsen, J.B. Christensen, M. Fourmigué, H.G. Madsen, N. Harrit, J. Org. Chem., 61(20) (1996) 6997-7005. https://doi.org/10.1021/jo960022x
T.T. Le, S.T. Phan, H.T.H. Le, H. Nguyen, T.T. Dang, T.T. Le, Molbank, 2021(2) (2021) M1210. https://doi.org/10.3390/M1210
