Research Progress of Fluorescent Organic Salts

doi:10.6023/cjoc202305004

Abstract

Organic salt fluorescent materials have the advantages of good photothermal stability, high melting point, good water solubility, strong electrostatic interactions and good biocompatibility due to their ionic nature, showing broad application prospects in the fields of biomonitoring, anti-counterfeiting and optical materials. Based on this, many organic salt luminescent materials with excellent properties, such as nitrogen heterocyclic aromatic onium salt, hydrazone salt, quaternary ammonium salt and quaternary phosphonium salt, have been developed. In this review, the molecular design, luminescence principle and recent progress of organic salt fluorescent materials are classified and summarized, and the development in this field is prospected.

Key words: organic salt, fluorescent materials, progress

Cite this article

Fen Wang, Lanting Wang, Gang Wang, Cheng Qian, Yingxia Zhou, Xin Zheng. Research Progress of Fluorescent Organic Salts[J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4147-4156.

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Fig. & Tab. 8

Scheme 1. Synthesis of compound 2 containing pyridinium salt group

Scheme 2. Syntheses of 2-phenyl-1H-benzimidazole and a series of benzimidazole salts 10、11 and 12

Scheme 3. Syntheses of several thiazole thiazole bridged imidazole salts 14a and 15a~15b

Scheme 4. Synthesis route of luminescent agent 16 (a) and the solid-state emission color change of luminescent agent 16 under 365 nm ultraviolet lamp irradiation by repeated grinding, fumigation or grinding heating (b)

Scheme 5. Synthesis of compound 24

Scheme 6. Synthesis of compound 25

Scheme 7. Luminous quaternary ammonium salts such as tetramethyl ammonium bromide (28), cetyltrimethylammonium bromide (compounds 30), cetyltrimethylammonium chloride (31) and cetyltriethylammonium iodide (32)

Scheme 8. Reversible conversion between compounds 33 and 34

References 50

[1]	Tao P.; Miao Y.; Wang H.; Xu B.; Zhao Q. Chem. Rec. 2019, 19, 1531. doi: 10.1002/tcr.v19.8
[2]	Liang Z. P.; Tang R.; Qiu Y. C.; Wang Y.; Lu H. B.; Wu Z. G. Acta Chim. Sinica 2021, 79, 1401. (in Chinese) doi: 10.6023/A21070355
	(梁志鹏, 唐瑞, 邱雨晨, 王阳, 陆洪彬, 吴正光, 化学学报, 2021, 79, 1401.) doi: 10.6023/A21070355
[3]	Li S. W.; Zhu C. Y. J.; Luo Y. H.; Zhang Y. R.; Teng H. M.; Wang Z. R.; Zhen R. G. Acta Chim. Sinica 2022, 80, 1600. (in Chinese) doi: 10.6023/A22080380
	(李善武, 朱陈宇杰, 罗尹豪, 张亚茹, 滕汉明, 王宗瑞, 甄永刚, 化学学报, 2022, 80, 1600.) doi: 10.6023/A22080380
[4]	Li J.; Wang J.; Li H.; Song N.; Wang D.; Tang B. Z. Chem. Soc. Rev. 2020, 49, 1144. doi: 10.1039/C9CS00495E
[5]	Zhang J.; Ye H.; Jin Y.; Han D. Top. Curr. Chem. 2022, 380, 1.
[6]	Dong S.; Li Z. J. Mater. Chem. C 2022, 10, 2431. doi: 10.1039/D1TC04598A
[7]	Zhou Y.; Qu J. ACS Appl. Mater. Interfaces 2017, 9, 3209. doi: 10.1021/acsami.6b12489
[8]	Berthiot R.; del Giudice N.; Douce L. Eur. J. Org. Chem. 2021, 2021, 4099. doi: 10.1002/ejoc.v2021.29
[9]	Chen X.; Yan L.; Liu Y.; Yang Y.; You J. Chem. Commun. 2020, 56, 15080. doi: 10.1039/D0CC06997C
[10]	Qin J.; Guo J.; Xu Q.; Zheng Z.; Mao H.; Yan F. ACS Appl. Mater. Interfaces 2017, 9, 10504. doi: 10.1021/acsami.7b00387
[11]	Park C.; Meghani N. M.; Shin Y.; Oh E.; Park J. B.; Cui J. H.; Tran T. T-D.; Tran P. H-L.; Lee B. J. Pharmaceutics 2019, 11, 102. doi: 10.3390/pharmaceutics11030102
[12]	Alam P.; He W.; Leung N. L.; Ma C.; Kwok R. T.; Lam J. W.; Sung H. H.; Ian D. Williams.; Wong K. S.; Tang B. Z. Adv. Funct. Mater. 2020, 30, 1909268. doi: 10.1002/adfm.v30.10
[13]	Yeung M. C. L.; Yam V. W. W. Chem. Soc. Rev. 2015, 44, 4192. doi: 10.1039/C4CS00391H
[14]	Hu H., Meier F., Zhao D., Abe Y., Gao Y., Chen B., Salim T.; Chia E. E.; Qiao X.; Deibel C.; Lam Y. M. Adv. Mater. 2018, 30, 1707621. doi: 10.1002/adma.v30.36
[15]	Wang S. J.; Lin Y.; Zhang C. K.; Zhu T.; Tian X. H.; Li D. D.; Ma W.; Zhang Q.; Wu J. Y.; Tian Y. P. Anal. Chem. 2022, 94, 4335. doi: 10.1021/acs.analchem.1c05052
[16]	Zuo Y.; Wang X.; Wu D. J. Mater. Chem. C 2019, 7, 14555. doi: 10.1039/C9TC05258E
[17]	Leduskrasts K.; Suna E. RSC Adv. 2019, 9, 460. doi: 10.1039/c8ra08771g
[18]	Asanuma Y.; Eguchi H.; Nishiyama H.; Tomita I.; Inagi S. Org. Lett. 2017, 19, 1824. doi: 10.1021/acs.orglett.7b00590 pmid: 28355080
[19]	Liu X.; Yang Z.; Xu W.; Chu Y.; Yang J.; Yan Y.; Wang Y.; Hua J. J. Mater. Chem. C 2019, 7, 12509. doi: 10.1039/C9TC04427B
[20]	Traven V. F.; Cheptsoy D. A. Russ. Chem. Rev. 2020, 89, 713. doi: 10.1070/RCR4909
[21]	Wang Z.; Bai W.; Tong J.; Wang Y. J.; Qin A.; Sun J. Z.; Tang B. Z. Chem. Commun. 2016, 52, 10365. doi: 10.1039/C6CC02851A
[22]	Chen R.; Gao X.; Cheng X.; Qin A.; Sun J. Z.; Tang B. Z. Polym. Chem. 2017, 8, 6277. doi: 10.1039/C7PY01378G
[23]	Tanabe K.; Suzui Y.; Hasegawa M.; Kato T. J. Am. Chem. Soc. 2012, 134, 5652. doi: 10.1021/ja3001979 pmid: 22372372
[24]	Li Y.; Zhuang J.; Lu Y.; Li N.; Gu M.; Xia J.; Zhao N.; Tang B. Z. ACS Nano 2021, 15, 20453. doi: 10.1021/acsnano.1c08928
[25]	Zhao X.; Chen Y.; Niu G.; Gu D.; Wang J.; Cao Y.; Yin Y.; Li X.; Ding D.; Xi R.; Meng M. ACS Appl. Mater. Interfaces 2019, 11, 13134. doi: 10.1021/acsami.9b02228
[26]	Choi S. Y.; Cho S.; Kim D.; Kim J.; Song G.; Singh R.; Kim C. J. Membrane Sci. 2021, 620, 118904. doi: 10.1016/j.memsci.2020.118904
[27]	Riduan S. N.; Zhang Y. Chem. Soc. Rev. 2013, 42, 9055. doi: 10.1039/c3cs60169b
[28]	Lü L. R.; Tang G. M.; Wang Y. T.; Ng S. W. J. Lumin. 2018, 199, 200. doi: 10.1016/j.jlumin.2018.02.064
[29]	Xie P. H.; Zhou Y.; Li X. C.; Liu X. J.; Liu L. J.; Cao Z. Q.; Wang J. J.; Zheng X. Chin. Chem. Lett. 2022.
[30]	Zhao N.; Yang Z.; Lam J. W.; Sung H. H.; Xie N.; Chen S.; Su H.; Gao M.; Ian D. W.; Kam S.; Tang B. Z. Chem. Commun. 2012, 48, 8637. doi: 10.1039/c2cc33780k
[31]	Wang J.; Gu X.; Ma H.; Peng Q.; Huang X.; Zheng X.; Sung S.; Shan G.; Lam J.; Shuai Z.; Tang B. Z. Nat. Commun. 2018, 9, 2963. doi: 10.1038/s41467-018-05298-y
[32]	Pawar A.; Korake S.; Pawar A.; Kamble R. Curr. Drug Delivery 2022.
[33]	Rokitskaya T. I.; Murphy M. P.; Skulachev V. P.; Antonenko Y. N. Bioelectrochemistry 2016, 111, 23. doi: 10.1016/j.bioelechem.2016.04.009 pmid: 27182824
[34]	Rokitskaya T. I.; Aleksandrova E. V.; Korshunova G. A.; Khailova L. S.; Tashlitsky V. N.; Luzhkov V. B.; Antonenko Y. N. J. Phys. Chem. 2022, 126, 412. doi: 10.1021/acs.jpcb.1c08135
[35]	Hu Q.; Gao M.; Feng G.; Liu B. Angew. Chem., Int. Edit. 2014, 53, 14225. doi: 10.1002/anie.v53.51
[36]	Zeng W.; Lin M. H.; Zhu L. Y.; Lin M. J. Chin. J. Chem. 2022, 40, 39. doi: 10.1002/cjoc.v40.1
[37]	Zhang Y.; Huo F.; Yin C.; Yue Y.; Hao J.; Chao J.; Liu D. Sens. Actuators, B 2015, 207, 59. doi: 10.1016/j.snb.2014.09.091
[38]	Wen T.; Luo J.; Jia K.; Lu L. Int. J. Heat Mass Transfer 2022, 190, 122761. doi: 10.1016/j.ijheatmasstransfer.2022.122761
[39]	Lee J. Y.; Selfridge K. M.; Kohn E. M.; Vaden T. D.; Caputo G. A. Biomolecules 2019, 9, 264. doi: 10.3390/biom9070264
[40]	Forman M. E.; Fletcher M. H.; Jennings M. C.; Duggan S. M.; Minbiole K. P.; Wuest W. M. ChemMedChem 2016, 11, 958. doi: 10.1002/cmdc.201600095 pmid: 27027389
[41]	Panzarasa G.; Osypova A.; Toncelli C.; Buhmann M. T.; Rottmar M.; Ren Q.; Maniura-Weber K.; Rossi R. M.; Boesel L. F. Sens. Actuators, B 2017, 249, 156. doi: 10.1016/j.snb.2017.04.045
[42]	Qiao F.; Ke J.; Liu Y.; Pei B.; Hu Q.; Tang B. Z.; Wang Z. Carbohydr. Polym. 2020, 230, 115614. doi: 10.1016/j.carbpol.2019.115614
[43]	Tong H.; Hong Y.; Dong Y.; Häußler M.; Lam J. W.; Li Z.; Guo Z.; Guo Z.; Tang B. Z. Chem. Commun. 2006, 3705.
[44]	Tang S.; Zhao Z.; Chen J.; Yang T.; Wang Y.; Chen X.; Lv M.; Yuan W. Z. Angew. Chem., Int. Edit. 2022, 134, e202117368. doi: 10.1002/ange.v134.16
[45]	Can N. Ö.; Osmaniye D.; Levent S.; Saǧllk B. N.; Inci B.; Ilgın S.; Özkay Y.; Kaplancıkll Z. A. Molecules 2017, 22, 1381. doi: 10.3390/molecules22081381
[46]	Rawat P.; Singh R. N.; Niranjan P.; Ranjan A.; Holguín N. R. F. J. Mol. Struct. 2017, 1149, 539. doi: 10.1016/j.molstruc.2017.08.008
[47]	Juwiyatri E.; Fauza S. N.; Afriana N. J. Phys.: Conf. Ser. 2021, 2049, 012050.
[48]	Filo J.; Tisovský P.; Csicsai K.; Donovalová J.; Gáplovský M.; Gáplovský A.; Cigáň M. RSC Adv. 2019, 9, 15910. doi: 10.1039/C9RA02906K
[49]	Tian D. J.; Zheng X.; Li X. C.; Liu X. J.; Zhao J. H.; Wang J. J. Chem.-Eur. J. 2019, 25, 16519. doi: 10.1002/chem.v25.72
[50]	Wang M. Y.; Shi J.; Mao H. L.; Sun Z.; Guo S. Y.; Guo J. N.; Yan F. Biomacromolecules 2019, 20, 3161. doi: 10.1021/acs.biomac.9b00741

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