Research Progress in High Brightness Near Infrared Fluorescent Dyes

doi:10.6023/cjoc202303043

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (11): 3745-3760.DOI: 10.6023/cjoc202303043 Previous Articles Next Articles

高亮度近红外荧光染料研究进展

邱建文^a, 刘梦^a, 熊新怡^a, 高勇^a^,^b^,^*(), 朱虎^a^,^c^,^*()

a 福建师范大学化学与材料学院福州 350117
b 福建师范大学福建省高分子材料重点实验室福建省先进材料化工基础重点实验室福州 350117
c 福建省师范大学生物医学材料与组织工程闽台科技合作基地工业生物催化福建省高校工程研究中心医学光电科学与技术教育部重点实验室福州 350117

收稿日期:2023-03-29 修回日期:2023-06-18 发布日期:2023-07-05
基金资助:
国家自然科学基金(U1805234); 福建省自然科学基金(2021J01147); 福建省高校创新团队培育计划、福建省百人计划、中央引导地方科技专项资金(2020L3008)

Research Progress in High Brightness Near Infrared Fluorescent Dyes

Jianwen Qiu^a, Meng Liu^a, Xinyi Xiong^a, Yong Gao^a^,^b(), Hu Zhu^a^,^c()

a College of Chemistry and Materials Science, Fujian Normal University, Fuzhou 350117
b Fujian Provincial Key Laboratory of Polymer Materials, Fujian Provincial Key Laboratory of Advanced Materials Oriented Chemical Engineering, Fujian Normal University, Fuzhou 350117
c Fujian-Taiwan Science and Technology Cooperation Base of Biomedical Materials and Tissue Engineering, Engineering Research Center of Industrial Biocatalysis, Key Laboratory of OptoElectronic Science and Technology for Medicine of Ministry of Education, Fujian Normal University, Fuzhou 350117

Received:2023-03-29 Revised:2023-06-18 Published:2023-07-05
Contact: * E-mail: gaoyong@fjnu.edu.cn; zhuhu@fjnu.edu.cn
Supported by:
National Natural Science Foundation of China(U1805234); Natural Science Foundation of Fujian Province(2021J01147); Program for Innovative Research Team in Science and Technology in Fujian Province University, the 100 Talents Program of Fujian Province and the Special Funds of the Central Government Guiding Local Science and Technology Development(2020L3008)

Abstract Due to the merits of near-infrared light (NIR) (650~1700 nm), such as deep tissue penetration, lower autofluore- scence interference in vivo, and little light damage to organisms, NIR dyes have been one of the research focuses in bioimaging. The narrow bandgaps of NIR dyes increase the probability of non-radiative transition of the excited state, resulting in a significant reduction of fluorescence intensity. Meanwhile, the longer conjugated hydrophobic skeleton and strong molecular charge transfer ability make NIR dyes easy to interact with external molecules, thus increasing the non-radiative energy loss and reducing the fluorescence intensity. To obtain NIR dyes with high brightness, researchers have made many improvements and modifications. From the perspective of the structure-property relationship of fluorescent dyes, the development of mainstream high-brightness near-infrared dyes is reviewed, hoping to provide assistance and guidance for the development of NIR fluorescent dyes with high-brightness.

Key words: high brightness, near infrared, fluorescence, dyes

Cite this article

Jianwen Qiu, Meng Liu, Xinyi Xiong, Yong Gao, Hu Zhu. Research Progress in High Brightness Near Infrared Fluorescent Dyes[J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3745-3760.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 22

Figure 1. Design strategy for small molecular dyes from the visible region to the near-infrared region

Figure 2. Jablonski diagram of the photophysical processes of organic small molecule fluorophores Abs., IC, Fluo., ISC, and phos. represent absorption, internal conversion, fluorescence, intersystem crossing and phosphorescence, respectively

Figure 3. Molecular structures of xanthene (a) and rhodamine dyes (b)

Figure. Molecular structure of xanthene dye 1

Figure 5. Molecular structures of xanthene dyes 2~9

Figure 6. Molecular structures and basic photophysical properties of xanthene dyes 10~13

Figure 7. Molecular structures and basic photophysical properties of xanthene dyes 14~20

Figure 8. Molecular structures and basic photophysical properties of xanthene dyes 21~22

Figure 9. Molecular structure of BODIPY

Figure 10. Molecular structures and basic photophysical properties of BODIPY dyes 23~30

Figure 11. Molecular structures and basic photophysical properties of BODIPY dyes 31~38

Figure 12. Molecular structures and basic photophysical properties of BODIPY dyes 39~42

Figure 13. Molecular structures and basic photophysical properties of BODIPY dyes 43~46

Figure 14. Molecular structure of cyanine dye

Figure 15. Molecular structures and basic photophysical properties of cyanine dyes 47~50

Figure 16. Molecular structures and basic photophysical properties of cyanine dyes 51~53

Figure 17. Molecular structures and basic photophysical properties of cyanine dyes 54~64

Figure 18. Molecular structures and basic photophysical properties of cyanine dyes 65~66

Figure 19. Molecular structure of oxazine dye

Figure 20. Molecular structures and basic photophysical properties of cyanine dyes 67~72

Figure 21. Molecular structures and basic photophysical properties of cyanine dyes 73~76

Figure 22. Molecular structures and basic photophysical properties of crossbreeding dyes 77~87

References 60

[1]	(a) Lei, Z.; Zhang, F. Angew. Chem., Int. Ed. 2021, 60, 16294. doi: 10.1002/anie.v60.30
	(b) Chen, Y.; Chen, S.; Yu, H.; Wang, Y.; Cui, M.; Wang, P; Sun, P.; Ji, M. Adv. Healthcare Mater. 2022, 11, 2201158. doi: 10.1002/adhm.v11.21
	(c) Yan, C.; Zhang, Y.; Guo, Z. Coord. Chem. Rev. 2021, 427, 213556. doi: 10.1016/j.ccr.2020.213556
	(d) Wang, Z.; Geng, H.; Nie, C.; Xing, C. Chin. J. Chem. 2022, 40, 759. doi: 10.1002/cjoc.v40.6
	(e) He, Y.; Liao, S.; Wang, Y. Chin. J. Chem. 2021, 39, 1435. doi: 10.1002/cjoc.v39.6
[2]	(a) Beija, M.; Afonso, C. A. M.; Martinho, J. M. G. Chem. Soc. Rev. 2009, 38, 2410. doi: 10.1039/b901612k pmid: 21796324
	(b) Boens, N.; Leen, V.; Dehaen, W. Chem. Soc. Rev. 2012, 41, 1130. doi: 10.1039/c1cs15132k pmid: 21796324
	(c) Cavazos‐Elizondo, D.; Aguirre‐Soto, A. Analysis Sensing 2022, 2, e202200004. doi: 10.1002/anse.v2.5 pmid: 21796324
	(d) Karaman, O.; Alkan, G. A.; Kizilenis, C.; Akgul, C. C.; Gunbas, G. Coord. Chem. Rev. 2023, 475, 214841. doi: 10.1016/j.ccr.2022.214841 pmid: 21796324
[3]	(a) Khan, Z.; Sekar, N. Dyes Pigm. 2022, 110735.
	(b) Wang, L.; Du, W.; Hu, Z.; Uvdal, K.; Lin, L.; Huang, W. Angew. Chem., Int. Ed. 2019, 58, 14026. doi: 10.1002/anie.v58.40
	(c) Li, J.; Zhao, M.; Huang, J.; Liu, P.; Luo, X.; Zhang, Y.; Yan, C.; Zhu, W.; Guo, Z. Coord. Chem. Rev. 2022, 473, 214813. doi: 10.1016/j.ccr.2022.214813
	(d) Bumagina, N. A.; Antina, E. V.; Ksenofontov, A. A.; Antina, L. A.; Kalyagin, A. A.; Berezin, M. B. Coord. Chem. Rev. 2022, 469, 214684. doi: 10.1016/j.ccr.2022.214684
	(e) Liu, B.; Wang, C.; Qian, Y. Acta Chim. Sinica 2022, 80,1071. (in Chinese) doi: 10.6023/A22040141
	(刘巴蒂, 王承俊, 钱鹰, 化学学报, 2022, 80, 1071.) doi: 10.6023/A22040141
[4]	(a) Poronik, Y. M.; Vygranenko, K. V.; Gryko, D.; Gryko, D. T. Chem. Soc. Rev. 2019, 48, 5242. doi: 10.1039/c9cs00166b pmid: 31549709
	(b) Zhu, S.; Tian, R.; Antaris, A. L.; Chen, X.; Dai, H. Adv. Mater. 2019, 31, 1900321. doi: 10.1002/adma.v31.24 pmid: 31549709
	(c) Ni, Y.; Wu, J. Org. Biomol. Chem. 2014, 12, 3774. doi: 10.1039/c3ob42554a pmid: 31549709
[5]	(a) Mayerhöffer, U.; Fimmel, B.; Würthner, F. Angew. Chem., Int. Ed. 2012, 51, 164. doi: 10.1002/anie.v51.1
	(b) Zhou, E. Y.; Knox, H. J.; Liu, C.; Zhao, W.; Chan, J. J. Am. Chem. Soc. 2019, 141, 17601. doi: 10.1021/jacs.9b06694
[6]	(a) Umezawa, K.; Citterio, D.; Suzuki, K. Anal. Sci. 2014, 30, 327. doi: 10.2116/analsci.30.327
	(b) Wu, J.; Shi, Z.; Zhu, L.; Li, J.; Han, X.; Xu, M.; Hao, S.; Fan, Y.; Shao, T.; Bai, H.; Peng, B.; Hu, W.; Liu, X.; Yao, C.; Li, L.; Huang, W. Adv. Opt. Mater. 2022, 10, 2102514. doi: 10.1002/adom.v10.8
[7]	Kowada, T.; Maeda, H.; Kikuchi, K. Chem. Soc. Rev. 2015, 44, 4953. doi: 10.1039/C5CS00030K
[8]	Sun, W.; Guo, S.; Hu, C.; Fan, J.; Peng, X. Chem. Rev. 2016, 116, 7768.
[9]	(a) Chen, X, Pradhan, T, Wang, F, Kim, J. S.; Yoon, J. Chem. Rev. 2012, 112, 1910. doi: 10.1021/cr200201z
	(b) Zhao, M.; Guo, Y.; Xu, W.; Zhao, Y.; Xie, H.; Li, H.; Chen, X.; Zhao, R.; Guo, D. Trends Anal. Chem. 2020, 122, 115704. doi: 10.1016/j.trac.2019.115704
	(c) Liu, D.; He, Z.; Zhao, Y.; Yang, Y.; Shi, W.; Li, X.; Ma, H. J. Am. Chem. Soc. 2021, 143, 17136. doi: 10.1021/jacs.1c07711
[10]	(a) Wang, C.; Chi, W.; Qiao, Q.; Tan, D.; Xu, Z.; Liu, X. Chem. Soc. Rev. 2021, 50, 12656. doi: 10.1039/D1CS00239B
	(b) Lv, X.; Gao, C.; Han, T.; Shi, H.; Guo, W. Chem. Commun. 2020, 56, 715. doi: 10.1039/C9CC09138F
[11]	(a) Koide, Y.; Urano, Y.; Hanaoka, K.; Terai, T.; Nagano, T. ACS Chem. Biol. 2011, 6, 600. doi: 10.1021/cb1002416 pmid: 30920803
	(b) Ogasawara, A.; Kamiya, M.; Sakamoto, K.; Kuriki, Y.; Fujita, K.; Komatsu, T.; Ueno, T.; Hanaoka, K.; Onoyama, H.; Abe, H.; Tsuji, Y.; Fujishiro, M.; Koike, K.; Fukayama, M.; Seto, Y.; Urano, Y. Bioconjugate Chem. 2019, 30, 1055. doi: 10.1021/acs.bioconjchem.9b00198 pmid: 30920803
	(c) Tang, W.; Gao, H.; Li, J.; Wang, X.; Zhou, Z.; Gai, L.; Feng, X. J.; Tian, J.; Lu, H.; Guo, Z. Chem. Asian J. 2020, 15, 2724. doi: 10.1002/asia.v15.17 pmid: 30920803
[12]	Koide, Y.; Urano, Y.; Hanaoka, K.; Piao, W.; Kusakabe, M.; Saito, N.; Terai, T.; Okabe, T.; Nagano, T. J. Am. Chem. Soc. 2012, 134, 5029. doi: 10.1021/ja210375e
[13]	Zhou, X.; Lai, R.; Beck, J. R.; Li, H.; Stains, C. I. Chem. Commun. 2016, 52, 12290. doi: 10.1039/C6CC05717A
[14]	Ren, T.; Xu, W.; Zhang, W.; Zhang, X.; Wang, Z.; Xiang, Z.; Yuan, L.; Zhang, X. J. Am. Chem. Soc. 2018, 14, 7716.
[15]	Li, J.; Dong, Y.; Wei, R.; Jiang, G.; Yao, C.; Lv, M.; Wu, Y.; Gardner, S. H.; Zhang, F.; Lucero, M. Y.; Huang, J.; Chen, H.; Ge, H.; Chan, J.; Chen, J.; Sun, H.; Luo, X.; Qian, X.; Yang, Y. J. Am. Chem. Soc. 2022, 144, 14351. doi: 10.1021/jacs.2c05826
[16]	Jiang, G.; Ren, T-B.; Este, E. D.; Xiong, M.; Xiong, B.; Johnsson, K.; Zhang, X-B.; Wang, L.; Yuan, L. Nat. Commun. 2022, 13, 2264. doi: 10.1038/s41467-022-29547-3
[17]	Jiang, G.; Lou, X.-F.; Zuo, S.; Liu, X.; Ren, T.-B.; Wang, L.; Zhang, X.-B.; Yuan, L. Angew. Chem., Int. Ed. 2023, 135, e202218613. doi: 10.1002/ange.v135.17
[18]	Grimm, J. B.; English, B. P.; Chen, J.; Slaughter, J. P.; Zhang, Z.; Revyakin, A.; Patel, R.; Macklin, J. J.; Normanno, D.; Singer, R. H.; Lionnet, T.; Lavis, L. D. Nat. Methods 2015, 12, 244. doi: 10.1038/nmeth.3256
[19]	Lv, X.; Gao, C.; Han, T.; Shi, H.; Guo, W. Chem. Commun. 2020, 56, 715. doi: 10.1039/C9CC09138F
[20]	Liu, J.; Sun, Y.; Zhang, H.; Shi, H.; Shi, Y.; Guo, W. ACS Appl. Mater. Interfaces 2016, 8, 22953. doi: 10.1021/acsami.6b08338
[21]	Grzybowski, M.; Taki, M.; Senda, K.; Sato, Y.; Ariyoshi, T.; Okada, Y.; Kawakami, R.; Imamura, T.; Yamaguchi, S. Angew. Chem., Int. Ed. 2018, 57, 10137. doi: 10.1002/anie.v57.32
[22]	Song, Y.; Zhang, X.; Shen, Z.; Yang, W.; Wei, J.; Li, S.; Wang, X.; Li, X.; He, Q.; Zhang, S.; Zhang, S.; Zhang, Q.; Gao, B. Anal. Chem. 2020, 92, 12137. doi: 10.1021/acs.analchem.9b04926
[23]	Liu, D.; He, Z.; Zhao, Y.; Yang, Y.; Shi, W.; Li, X.; Ma. H. J. Am. Chem. Soc. 2021, 143, 17136. doi: 10.1021/jacs.1c07711
[24]	(a) Kamkaew, A.; Lim, S. H.; Lee, H. B.; Kiew, L. V.; Chung, L. Y.; Burgess, K. Chem. Soc. Rev. 2013, 42, 77. doi: 10.1039/C2CS35216H
	(b) Wu, P.; Zhu, Y.; Liu, S.; Xiong, H. ACS Cent. Sci. 2021, 7, 2039. doi: 10.1021/acscentsci.1c01066
	(c) Cheng, H.; Cao, X.; Zhang, S.; Zhang, K.; Cheng, Y.; Wang, J.; Zhao, J.; Zhou, L.; Liang, X.; Yoon, J. Adv. Mater. 2022, 2207546.
[25]	Ziessel, R.; Rihn, S.; Harriman, A. Chem. Eur. J. 2010, 16, 11942. doi: 10.1002/chem.v16:39
[26]	Li, Y.; Qiao, Z.; Li, T.; Zeika, O.; Leo, P. ChemPhotoChem 2018, 2, 1017. doi: 10.1002/cptc.v2.12
[27]	Rappitsch, T.; Borisov, S. M. Chem.-Eur. J. 2021, 27, 10685. doi: 10.1002/chem.202100965 pmid: 33950529
[28]	Chen, J.; Mizumura, M.; Shinokubo, H.; Osuka, A. Chem. Eur. J. 2009, 15, 5942. doi: 10.1002/chem.v15:24
[29]	Zhang, H.; Liu, J.; Sun, Y-Q.; Liu, M.; Guo, W. J. Am. Chem. Soc. 2020, 142, 17069. doi: 10.1021/jacs.0c06916
[30]	Taguchi, D.; Nakamura, T.; Horiuchi, H.; Saikawa, M.; Nabeshima, T. J. Org. Chem. 2018, 83, 5331. doi: 10.1021/acs.joc.8b00782
[31]	Deckers, J.; Cardeynaels, T.; Doria, S.; Tumanov, N.; Lapini, A.; Ethirajan, A.; Ameloot, M.; Wouters, J.; Donato, M. D.; Champagne, B.; Maes, W. J. Mater. Chem. C 2022, 10, 9344. doi: 10.1039/D2TC01526A
[32]	Killoran, J.; Allen, L.; Gallagher, J. F.; Gallagherb, W. M.; O′Shea, D. F. Chem. Commun. 2002, 17, 1862.
[33]	Gorman, A.; Killoran, J.; O'Shea, C.; Kenna, T.; Gallagher, W. M.; O'Shea, D. F. J. Am. Chem. Soc. 2004, 126, 10619. doi: 10.1021/ja047649e
[34]	Jiao, L.; Wu, Y.; Ding, Y.; Wang, S.; Zhang, P.; Yu, C.; Wei, Y.; Mu, X.; Hao, E. Chem.-Eur. J. 2014, 9, 805.
[35]	Lv, X.; Han, T.; Wu, Y.; Zhang, B.; Guo, W. Chem. Commun. 2021, 57, 9744. doi: 10.1039/D1CC03360C
[36]	Bai, L.; Sun, P.; Liu, Y.; Zhang, H.; Hu, W.; Zhang, W.; Liu, Z.; Fan, Q.; Li, L.; Huang, W. Chem. Commun. 2019, 55, 10920. doi: 10.1039/C9CC03378E
[37]	Zhang, Q.; Peng, Y. P.; Fan, Y.; Sun, C.; He, H.; Liu, X.; Lu, L.; Zhao, M.; Zhang, H.; Zhang, F. Angew. Chem. Int. Ed. 2021, 60, 3967. doi: 10.1002/anie.v60.8
[38]	(a) Mustroph, H. Phys. Sci. Rev. 2020, 5(5), 20190145.
	(b) Li, Y.; Zhou, Y.; Yue, X.; Dai, Z. Adv. Healthcare Mater. 2020, 9, 2001327. doi: 10.1002/adhm.v9.22
[39]	Matikonda, S. S.; Hammersley, G.; Kumari, N.; Grabenhorst, L.; Glembockyte, V.; Tinnefeld, P.; Ivanic, J.; Levitus, M.; Schner- mann, M. J. J. Org. Chem. 2020, 85, 5907. doi: 10.1021/acs.joc.0c00236
[40]	Ran, X.; Chen, P.; Liu, Y.; Shi, L.; Chen, X.; Liu, Y.; Zhang, H.; Zhang, L.; Kun Li, K.; Yu, X. Adv. Mater. 2023, 35, 2210179. doi: 10.1002/adma.v35.12
[41]	Li, D. H.; Schreiber, C. L.; Smith, B. D. Angew. Chem., Int. Ed 2020, 132, 2252.
[42]	Li, D.-H.; Gamage, R. S.; Oliver, A. G.; Patel, N. L.; Usama, S. M.; Kalen, J. D.; Schnermann, M. J.; Smith, B. D. Angew. Chem., Int. Ed. 2023, e202305062.
[43]	Cosco, E. D.; Caram, J. R.; Bruns, O. T.; Franke, D.; Day, R. A.; Farr, E. P.; Bawendi, G. M.; Sletten, E. M. Angew. Chem., Int. Ed. 2017, 56, 13126. doi: 10.1002/anie.v56.42
[44]	Cosco, E. D.; Arús, B. A.; Spearman, A. L.; Atallah, T. L.; Lim, I.; Leland, O. S.; Caram, J. R.; Bischof, T. S.; Bruns, O. T.; Sletten, E. M. J. Am. Chem. Soc. 2021, 143, 6836. doi: 10.1021/jacs.0c11599
[45]	Ndaleh, D.; Smith, C.; Yaddehige, M. L.; Shaik, A. K.; Watkins, D. L.; Hammer, N. I.; Delcamp, J. H. J. Org. Chem. 2021, 86, 15376. doi: 10.1021/acs.joc.1c01908 pmid: 34647452
[46]	Mujumdar, S. R.; Mujumdar, R. B.; Grant, C. M.; Waggoner, A. S. Bioconjugate Chem. 1996, 7, 356. pmid: 8816960
[47]	Cha, J.; Nani, R. R.; Luciano, M. P.; Kline, G.; Broch, A.; Kim, K.; Namgoong, J.-M.; Kulkarni, R. A.; Meier, J. L.; Kim, P.; Schner- mann, M. J. Bioorg. Med. Chem. Lett. 2018, 28, 2741. doi: 10.1016/j.bmcl.2018.02.040
[48]	Luciano, M. P.; Crooke, S. N.; Nourian, S.; Dingle, I.; Nani, R. R.; Gabriel Kline, G.; Patel, N. L.; Robinson, C. M.; Difilippantonio, S.; Kalen, J. D.; Finn, M. G.; Schnermann, M. J. ACS Chem. Biol. 2019, 14, 934.
[49]	(a) Anzalone, A. V.; Wang, T. Y.; Chen, Z.; Cornish V. W. Angew. Chem., Int. Ed. 2013, 125, 650.
	(b) Pauff, S. M.; Miller, S. C. J. Org. Chem. 2013, 78, 711. doi: 10.1021/jo302065u
[50]	(a) Shang, J.; Zhang, X.; He, Z.; Shen, S.; Liu, D.; Shi, W.; Ma, H. Angew. Chem., Int. Ed. 2022, 61, e2022050.
	(b) Li, W.; Yin, S.; Shen, Y.; Li, H.; Yuan, L.; Zhang, X.-B. J. Am. Chem. Soc. 2023, 145, 3736. doi: 10.1021/jacs.2c13222
	(c) Wei, P.; Guo, Y.; Liu, L.; Zhou, X.; Yi, T. J. Mater. Chem. B 2022, 10, 5211. doi: 10.1039/D2TB00765G
[51]	Wang, C.; Qiao, Q.; Chi, W.; Chen, J.; Liu, W.; Tan, D.; McKechnie, S.; Lyu, D.; Jiang, X.-F.; Zhou, W.; Xu, N.; Zhang, Q.; Xu, Z.; Liu, X. Angew. Chem., Int. Ed. 2020, 59, 10160. doi: 10.1002/anie.v59.25
[52]	Wang, L.; Liu, J.; Zhao, S.; Zhang, H.; Sun, Y.; Wei, A.; Guo, W. Chem. Commun. 2020, 56, 7718. doi: 10.1039/D0CC02322A
[53]	For the properties of ATTO dyes, see:
[54]	(a) Yuan, L.; Lin, W.; Yang, Y.; Chen, H. J. Am. Chem. Soc. 2012, 134, 1200. doi: 10.1021/ja209292b pmid: 22816866
	(b) Yuan, L.; Weiying Lin, W.; Zhao, S.; Gao, W.; Chen, B.; He, L.; Zhu, S. J. Am. Chem. Soc. 2012, 134, 13510. doi: 10.1021/ja305802v pmid: 22816866
[55]	Chen, H.; Lin, W.; Cui, H.; Jiang, W. Chem.-Eur. J. 2015, 21, 733. doi: 10.1002/chem.201404718 pmid: 25388080
[56]	Ren, T.-B.; Wang, Z.-Y.; Xiang, Z.; Lu, P.; Lai, H.-H.; Yuan, L.; Zhang, X.-B.; Tan, W. Angew. Chem., Int. Ed. 2021, 60, 800. doi: 10.1002/anie.v60.2
[57]	Ong, M. J. H.; Debieu, S.; Moreau, M.; Romieu, A. Richard J. Chem. Asian J. 2017, 12, 936.
[58]	Wang, S.; Li, B.; Zhang, F. ACS Cent. Sci. 2020, 6, 1302. doi: 10.1021/acscentsci.0c00544
[59]	Hara, D.; Uno, S.; Motoki, T.; Kazuta, Y.; Norimine, Y.; Suganuma, M.; Fujiyama, S.; Shimaoka, Y.; Yamashita, K.; Okada, M.; Nishikawa, Y.; Amino, H.; Iwanaga, S. J. Phys. Chem. B 2021, 125, 8703. doi: 10.1021/acs.jpcb.1c03193
[60]	Li, N.; Wang, T.; Wang, N.; Fan, M.; Cui, X. Angew. Chem., Int. Ed. 2022, e202217326.

高亮度近红外荧光染料研究进展

Research Progress in High Brightness Near Infrared Fluorescent Dyes

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 22

References 60

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Simin Wu, Jiaxin Tang, Yujia Zhou, Xuetao Xu, Haoxing Zhang, Shaohua Wang. α-Glucosidase Inhibition Research of Derivatives Based on 2β-Acetoxyferruginol Scaffold Excluding Acetic Acid Group [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 613-621.
[2]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[3]	Lijun Xu, Zongjun Li, Fushe Han, Xiang Gao. N,N-Dimethylformamide-Promoted Synthesis of Fullerene-Fused Oxazoline Derivatives [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 242-250.
[4]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[5]	Li Guan, Yanyan Zhou, Yongbao Mao, Kaisen Fu, Wenhui Guan, Yile Fu. Research Progress in the Synthesis of Polymethine Chain Modified Cyanine Dyes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2682-2698.
[6]	Kaichun Liang, Keyan Bai, Lei Dai, Yuan Liu, Zecong Ye, Yanping Huo. Design, Synthesis and Electroluminescent Properties of Multiresonant Thermally Activated Delayed Fluorescence Materials Based on Tetrahydroquinoline [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1799-1807.
[7]	Yi Zhang, Cheng-Zhuo Du, Ji-Kun Li, Xiao-Ye Wang. Recent Advances in Multi-Resonance Thermally Activated Delayed Fluorescence Materials Based on B,N-Heteroarenes [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1645-1690.
[8]	Xiaodong Yang, Xiaokang Zheng, Hailiang Dong, Jing Sun, Hua Wang. Research Progress of Circularly Polarized Thermally Activated Delayed Fluorescence Materials and Devices [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1292-1309.
[9]	Wu Zhou, Min Peng, Qingxiang Liang, Aibin Wu, Wenming Shu, Weichu Yu. A Novel Turn-On Fluorescent Probe Based on Naphthalimide for Highly Selective and Sensitive Detection of Hydrogen Sulfide in Solution and Gas [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4277-4283.
[10]	Yuehua Zhang, Fei Nie, Lu Zhou, Xiaofeng Wang, Yuan Liu, Yanping Huo, Wencheng Chen, Zujin Zhao. Synthesis and Optoelectronic Studies of Thermally Activated Delayed Fluorescence Materials Based on Benzothiazolyl Ketones [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3876-3887.
[11]	Xiaoyang Xu, Meiyan Liu, Chenglong Li, Xiaoming Wu, Xuguang Liu. Recent Advance of 1,4-BN Heteroaromatics in China [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3826-3843.
[12]	Yanhui Ma, Yuqian Wu, Xiaoxu Wang, Gui Gao, Xin Zhou. Research Progress of Near-Infrared Fluorescent Probes Based on 1,3-Dichloro-7-hydroxy-9,9-dimethyl-2(9H)-acridone (DDAO) [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 94-111.
[13]	Yaxin Yang, Lin Chen, Xiaoling Hu, Keli Zhong, Shidi Li, Xiaomei Yan, Jinglin Zhang, Lijun Tang. Synthesis of a Turn-On Fluorescent Probe for Hydrogen Sulfide and Its Application in Red Wine and Living Cells [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 308-312.
[14]	Siyi Zhou, Xu Ding, Yongmei Zhao, Jinghua Li, Wen Luo. A Flavone-Based Long-Wavelength Fluorescent Probe to Detect Biothiols in vitro and in vivo [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 178-185.
[15]	Binghan Lin, Jibin Zhuo, Caixia Lin, Yong Gao, Yaofeng Yuan. Synthesis and Nucleotide Recognition Properties of Carborane-Based Benzoimidazolium Cyclophane [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2551-2558.