MONOARYLATION OF DIPHENYLDITHIENYLETHENE BY LIGAND-FREE PALLADIUM CATALYZED C-H ACTIVATION
Main Article Content
Abstract
This work reports on a green and convenient methodology for the arylation of diphenyldithienylethene by direct ligand-free palladium-catalyzed C–H bond functionalization. Based on this approach, a new diphenyldithienylethene-based compound with aryl substituent
DTE-3-CHO-1 was successfully synthesized from thiophene via four steps. These compounds were structurally identified by NMR and HR-MS spectral analyses.
Keywords
aggregation-induced emission, diphenyldithienylethene, direct palladium-catalyzed arylation, fluorescence
Article Details
References
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Hong, Y., Lam, J. W. Y., & Tang, B. Z. (2011). Aggregation-Induced Emission. Chemical Society Reviews, 40, 5361-5388.
Li, Y., Li, Z., Wang, Y., Compaan, A., Ren, T., & Dong, W. J. (2013). Increasing the power output of a CdTe solar cell via luminescent down shifting molecules with intramolecular charge transfer and aggregation induced emission characteristics. Energy & Environmental Science, 6, 2907-2911.
Lin, E. E., Wu, J. Q., Schäfers, F. , Su, X.-X., Wang, K.-F., Li, J. L., Chen, Y., Zhao, X., Ti, H., Li, Q., Ou, T. M., Glorius, F., & Wang, H. (2019). Regio- and stereoselective synthesis of tetra- and triarylethenes by N-methylimidodiacetyl boron-directed palladium-catalysed three-component coupling. Communications Chemistry, 2(34).
Liu, X., Liang, G. (2017). Dual aggregation-induced emission for enhanced fluorescence sensing of furin activity in vitro and in living cells. Chemical Communications, 53, 1037–1040.
Mei, J., Leung, N. L. C., Kwok, R. T. K., Lam, J. W. Y., & Tang, B. Z. (2015). Aggregation-Induced Emission: Together We Shine, United We Soar!. Chemical Reiews, 115(21),
11718-11940.
Mlostoń, G., Urbaniak, K., Pawlak, A., & Heimgartner, H. (2016). New Applications of Hetaryl Thioketones for the Synthesis of Hetaryl-Substituted Ethenes via 'Two-Fold Extrusion Reaction'. Heterocycles, 93, 127-139.
Rananaware, A., Bhosale, R. S., Ohkubo, K., Patil, H., Jones, L. A., Jackson, S. L., Fukuzumi, S., Bhosale, S. V., & Bhosale, S. V. (2015). Tetraphenylethene-Based Star Shaped Porphyrins: Synthesis, Selfassembly, and Optical and Photophysical Study. Journal of Organic Chemistry, 80(8), 3832-3840.
Shi, J., Deng, Q., Li, Y., Zheng, Z., Shangguan, H., Li, L., Huang, F., & Tang, B. (2019). Homogeneous probing of lipase and -amylase simultaneously by AIEgens, Chemical Communications, 55, 6417-6420.
Zhang, M., Yao, Y., Stang, P. J., & Zhao, W. (2020). Divergent and Stereoselective Synthesis of Tetraarylethylenes from Vinylboronates. Angewandte Chemie International Edition, 59(45), 20090-20098.
Zhang, G. F., Wang, H., Aldred, M. P., Chen, T., Chen, Z. Q., Meng, X., & Zhu, M. Q. (2014). General Synthetic Approach toward Geminal-Substituted Tetraarylethene Fluorophores with Tunable Emission Properties: X ray Crystallography, Aggregation-Induced Emission and Piezofluorochromism. Chemistry of Materials, 26, 4433-4446.
Zhao, Z., Lu, P., Lam, J. W. Y., Wang, Z., Chan, C. Y. K., Sung, H. H. Y., Williams, I. D., Mab, Y., & Tang, B. Z. (2011). Molecular anchors in the solid state: Restriction of intramolecular rotation boosts emission efficiency of luminogen aggregates to unity. Chemical Science, 2, 672-675
Wang, X., Zhang, C., Xu, Y., He, Q., Mu, P., Chen, Y., Zeng, J., Wang, F., & Jiang, J. X. (2018). Conjugated Microporous Polytetra(2-Thienyl)ethylene as High Performance Anode Material for Lithiumand Sodium-Ion Batteries. Macromolecular Chemistry and Physics, 219(7), 1700524-1700532.