Design and Synthesis of Near-infrared Fluorescent Dyes of Difluoroboron β-diketonate and Cell Imaging

doi:10.6023/cjoc202404032

Chinese Journal of Organic Chemistry

ARTICLE

二氟化硼β-二酮类近红外荧光染料的设计合成及细胞成像研究

齐云鹏^*,a, 刘伟^a, 王俊龙^a, 杜涛^a, 矫淞霖^a

^a伊犁师范大学化学化工学院新疆普通高等学校天然产物化学与应用重点实验室新疆生物质资源清洁转化与高值利用重点实验室新疆伊宁 835000

收稿日期:2024-04-22 修回日期:2024-06-01
基金资助:
新疆维吾尔自治区自然科学基金((No. 2022D01C338)资助项目、伊犁师范大学科研项目((No. 2022HJYB05).

Design and Synthesis of Near-infrared Fluorescent Dyes of Difluoroboron β-diketonate and Cell Imaging

Qi Yunpeng^*,a, Liu Wei^a, Wang Junlong^a, Du Tao^a, Jiao Songlin^a

^aSchool of Chemistry and Chemical Engineering, University and College Key Lab of Natural Product Chemistry and Application in Xinjiang, Xinjiang Key Laboratory of Clean Conversion and High Value Utilization of Biomass Resources, Yili Normal University, Yining 835000, China

Received:2024-04-22 Revised:2024-06-01
Contact: *E-mail:17988326@ylnu.edu.cn
Supported by:
Natural Science Foundation of Xinjiang Uygur Autonomous Region (No. 2022D01C338), Scientific Research Project of Yili Normal University (No. 2022HJYB05).

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Abstract

Near-infrared (NIR) luminescent materials have great potential in the field of bioimaging due to their unique advantages of strong tissue penetration and weak light scattering in biological tissues. In this study, a donor-acceptor (D-A) structured boron difluoride β-diketonate complex (TPA-BF₂-CN) was designed and synthesized through the strategy of enhancing intramolecular charge transfer. This complex exhibits solvent-dependent luminescent properties. It demonstrates good luminescence efficiency in dilute solution and solid state, with efficiencies of 11.1% and 5.9% respectively. The maximum emission wavelength peaks at 760 nm, falling within the NIR range. The complex also possesses mechanochromic properties, with a redshift of emission wavelength by 107 nm after grinding. TPA-BF₂-CN exhibits dual emission fluorescence phenomenon, with emission peaks located in the blue light region at 400 nm and the NIR region at 760 nm, with an emission wavelength range of 690-850 nm in the NIR region. Compared to single-channel fluorescent molecules, it has the advantage of avoiding interference from environmental factors. Cell imaging studies demonstrate good compatibility of TPA-BF₂-CN with HeLa cells, and NIR emission signals can be observed throughout the cytoplasmic region of HeLa cells. Therefore, TPA-BF₂-CN can serve as a fluorescent probe for live cell imaging.

Key words: difluoroboron β-diketonate, near-infrared, cell imaging, mechanochromic, dual-state emission

Cite this article

Qi Yunpeng, Liu Wei, Wang Junlong, Du Tao, Jiao Songlin. Design and Synthesis of Near-infrared Fluorescent Dyes of Difluoroboron β-diketonate and Cell Imaging[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202404032.

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二氟化硼β-二酮类近红外荧光染料的设计合成及细胞成像研究

Design and Synthesis of Near-infrared Fluorescent Dyes of Difluoroboron β-diketonate and Cell Imaging

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