Chinese Journal of Organic Chemistry >
Design and Synthesis of Near-Infrared Fluorescent Dyes of Difluoroboron β-Diketonate and Cell Imaging
Received date: 2024-04-22
Revised date: 2024-06-01
Online published: 2024-07-10
Supported by
Natural Science Foundation of Xinjiang Uygur Autonomous Region(2022D01C338); Scientific Research Project of Yili Normal University(2022HJYB05)
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.
Yunpeng Qi , Wei Liu , Junlong Wang , Tao Du , Songlin Jiao . Design and Synthesis of Near-Infrared Fluorescent Dyes of Difluoroboron β-Diketonate and Cell Imaging[J]. Chinese Journal of Organic Chemistry, 2024 , 44(11) : 3357 -3364 . DOI: 10.6023/cjoc202404032
| [1] | Lei Z.; Zhang F. Angew. Chem., Int. Ed. 2021, 60, 16294. |
| [2] | Li H.; Kim Y.; Jung H.; Hyun J. Y.; Shin I. Chem. Soc. Rev. 2022, 51, 8957. |
| [3] | Chen Y.; Chen S.; Yu H.; Wang Y.; Cui M.; Wang P. Adv. Healthcare Mater. 2022, 11, 2201158. |
| [4] | Wang Z.; Geng H.; Nie C.; Xing C. Chin. J. Chem. 2022, 40, 759. |
| [5] | He Y.; Liao S.; Wang Y. Chin. J. Chem. 2021, 39, 1435. |
| [6] | He X. M.; Yuan F.; Zhang S. Y.; Zhang J. J. Acta Chim. Sinica 2023, 81, 1515 (in Chinese). |
| [6] | (贺晓梦, 袁方, 张素雅, 张健健, 化学学报, 2023, 81, 1515.) |
| [7] | Boens N.; Leen V.; Dehaen W. Chem. Soc. Rev. 2012, 41, 1130. |
| [8] | Beija M.; Afonso C. A. M.; Martinho J. M. G. Chem. Soc. Rev. 2009, 38, 2410. |
| [9] | Wan Y.; Lu G.; Wei W. C.; Huang Y. H.; Li S.; Chen J. X. ACS Nano 2020, 14, 9917. |
| [10] | Li L.; Shao C.; Liu T.; Chao Z.; Chen H.; Xiao F. Adv. Mater. 2020, 32, 2003471. |
| [11] | Luo J.; Xie Z.; Lam J. W. Y.; Cheng L.; Chen H.; Tang B. Z. Chem. Commun. 2001, 18, 1740. |
| [12] | Mei J.; Hong Y.; Lam J. W. Y.; Qin A.; Tang Y.; Tang B. Z. Adv. Mater. 2014, 26, 5429. |
| [13] | Mei J.; Leung N. L. C.; Kwok R. T. K.; Lam J. W. Y.; Tang B. Z. Chem. Rev. 2015, 115, 11718. |
| [14] | Xu W.; Wang D.; Tang B. Z. Angew. Chem., Int. Ed. 2021, 60, 7476. |
| [15] | Collot M. Mater. Horiz. 2021, 8, 501. |
| [16] | Qi Y.; Wang Y.; Ge G.; Liu Z.; Yu Y.; Xue M. J. Mater. Chem. C 2017, 5, 11030. |
| [17] | Qi Y.; Wang Y.; Yu Y.; Liu Z.; Zhang Y.; Du G. RSC Adv. 2016, 6, 33755. |
| [18] | Qi Y.; Liu W.; Wang Y.; Ma L.; Yu Y.; Zhang Y. New J. Chem. 2018, 42, 11373. |
| [19] | Yu C. J.; Huang Z. L.; Wang X. R.; Miao W.; Wu Q. H.; Wong W. Y. Org. Lett. 2018, 20, 4462. |
| [20] | Lv X.; Wu Y.; Zhang B. R.; Guo W. Acta Chim. Sinica 2023, 81, 359 (in Chinese). |
| [20] | (吕鑫, 吴仪, 张勃然, 郭炜, 化学学报, 2023, 81, 359.) |
| [21] | Cui L.; Shinjo H.; Ichiki T.; Deyama K.; Harada T.; Ishibashi K. Angew. Chem., nt. Ed. 2022, 61, e202204358. |
| [22] | Mirochnik A. G.; Puzyrkov Z. N.; Fedorenko E. V.; Svistunova I. V.; Markova A. A.; Shibaeva A. V. Spectrochim. Acta, Part A 2023, 291, 122319. |
| [23] | Fabian J.; Hartmann H. J. Phys. Org. Chem. 2004, 17, 359. |
| [24] | Chen P. Z.; Niu L. Y.; Chen Y. Z.; Yang Q. Z. Coord. Chem. Rev. 2017, 350, 196. |
| [25] | Cao J.-J. Ph.D. Dissertation, Jilin University, Changchun, 2023 (in Chinese). |
| [25] | (曹靖劼, 博士论文, 吉林大学, 长春, 2023.) |
| [26] | Liu N.; Chen P. Z.; Wang J. X.; Niu L. Y.; Yang Q. Z. Chin. Chem. Lett. 2019, 30, 1939. |
| [27] | Felouat A.; D’Aléo A.; Fages F. J. Org. Chem. 2013, 78, 4446. |
| [28] | Hu R.; Lager E.; Aguilar-Aguilar A.; Liu J.; Lam J. W. Y.; Sung H. H. Y. J. Phys. Chem. C 2009, 113, 15845. |
| [29] | Zeng Q.; Li Z.; Dong Y.; Di C.; Qin A.; Hong Y. Chem. Commun. 2007, 70. |
| [30] | Liu J.; He T.; Gong Z. L.; Liang N.; Feng Y.; Long G. Adv. Opt. Mater. 2023, 12, 2302486. |
| [31] | Zhao Y.; Chen P.; Han L.; Wang E. Chin. J. Org. Chem. 2023, 43, 2454 (in Chinese). |
| [31] | (赵洋, 陈盼盼, 韩立志, 王恩举, 有机化学, 2023, 43, 2454.) |
| [32] | Zhang G.; Lu J.; Sabat M.; Fraser C. L. J. Am. Chem. Soc. 2010, 132, 2160. |
| [33] | Yoon S.-J.; Chung J. W.; Gierschner J.; Kim K. S.; Choi M.-G.; Kim D. J. Am. Chem. Soc. 2010, 132, 13675. |
| [34] | Cai F. Z.; Xu Y. L.; Zhou L.; Xu B. S.; Chen H.; Sun J. Q. Chin. J. Appl. Chem. 2020, 37, 440 (in Chinese). |
| [34] | (蔡丰泽, 徐永玲, 周乐, 许丙嵩, 陈浩, 孙建强, 应用化学, 2020, 37, 440.) |
| [35] | Qiu Q. Q.; Xu P. F.; Zhu Y. J.; Yu J. R.; Wei M. R.; Xi W. B.; Feng H.; Chen J. R.; Qian Z. S. Chem.-Eur. J. 2019, 25, 15983. |
/
| 〈 |
|
〉 |
