Mono aryl hóa diphenyldithienylethene thông qua phản ứng hoạt hóa trực tiếp liên kết C-H sử dụng xúc tác palladium không ligand

Chỉ số đề mục

Lĩnh vực nghiên cứu

Hóa phân tích

Dạng tài liệu

Tác giả

Lê Tín Thanh, Nguyễn Thị Phương Nhi, Nguyễn Hiển⁽¹⁾, Lê Thị Hồng Hải, Lê Thanh Thanh, Đặng Thanh Tùng

Nhan đề

Mono aryl hóa diphenyldithienylethene thông qua phản ứng hoạt hóa trực tiếp liên kết C-H sử dụng xúc tác palladium không ligand

Nhan đề tiếng anh

Monoarylation of diphenyldithienylethene by ligand-free palladium catalyzed c-h activation

Nguồn trích

Tạp chí Khoa học - Đại học Sư phạm TP Hồ Chí Minh

Năm xuất bản

2021

Số

9

Trang

1559-1564

ISSN

1859-3100

Từ khóa

Aggregation-induced emission, Diphenyldithienylethene, Phản ứng aryl hoá trực tiếp xúc tác palladium, Fluorescence

Từ khóa tiếng anh

Aggregation-induced emission, Diphenyldithienylethene, Direct palladium-catalyzed arylation, Fluorescence

Tóm tắt

Bài báo trình bày một phương pháp hiệu quả để thực hiện aryl hoá diphenyldithienylethene thông qua phản ứng hoạt hoá trực tiếp liên kết C-H sử dụng xúc tác palladium không ligand. Hợp chất diphenyldithienylethene DTE-3-CHO-1 được tổng hợp từ thiophene qua bốn giai đoạn. Giai đoạn chìa khoá của quá trình tổng hợp DTE-3-CHO-1 là phản ứng hoạt hoá trực tiếp liên kết C-H được thực hiện giữa diphenyldithienylethene 3 và 3-bromobenzaldehyde sử dụng xúc tác Pd(OAc)2, base KOAc trong dung môi DMAc tại 120 ^oC trong 16h. DTE-3-CHO-1 thu được với hiệu suất 49%. Hợp chất DTE-3-CHO-1 tổng hợp được hứa hẹn là một hợp chất có các tính chất quang lí hấp dẫn. Cấu trúc của diphenyldithienylethene DTE-3-CHO-1 cũng như các hợp chất trung gian trong quá trình tổng hợp được xác định dựa vào phổ NMR và HR-MS. Hợp chất DTE-3-CHO-1 là một hợp chất mới.

Tóm tắt tiếng anh

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

Kí hiệu kho

TTKHCNQG, CTv 138

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Tài liệu tham khảo

[1] 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.
[2] 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
[3] 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.
[4] Zhang, M., Yao, Y., Stang, P. J., & Zhao, W. (2020), Divergent and Stereose-lective Synthesis of Tetraarylethylenes f-rom Vinylboronates.,Angewandte Chemie International Edition, 59(45), 20090-20098.
[5] 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.
[6] 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
[7] 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
[8] 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.
[9] 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
[10] 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 stereose-lective synthesis of tetraand triarylethenes by N-methylimidodiacetyl boron-directed palladium-catalysed threecomponent coupling,Communications Chemistry, 2(34).
[11] 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 c-harge transfer and aggregation induced emission c-haracteristics,Energy & Environmental Science, 6, 2907-2911.
[12] Hong, Y., Lam, J. W. Y., & Tang, B. Z. (2011), Aggregation-Induced Emission.,Chemical Society Reviews, 40, 5361-5388.
[13] Chang, Z. F., Jing, L. M., Liu, Y. Y., Liu, J. J., Ye, Y. C., Zhao, Y. S., Yuan, S. C., & Wang, J. L. (2016), Constructing small molecular AIE luminophores through a 2, 2-(2, 2-diphenylethene1, 1-diyl) dithiophene core and peripheral triphenylamine with applications in piezofluorochromism, optical waveguides, and explosive detection,Journal of Materials Chemistry C, 4, 8407-8415.
[14] Bottalico, D., Fiandanese, V., Marchese, G., & Punzi, A. (2009), Synthesis of Symmetrical Ketones f-rom Grignard Reagents and 1,1’-Carbonyldiimidazole,Synthesis, 14, 2316-2318