有机盐发光材料研究进展

doi:10.6023/cjoc202305004

摘要/Abstract

有机盐发光材料因其离子性而具有光热稳定性好、熔点高、水溶性好、强静电相互作用及生物相容性好等优点, 在生物监测、防伪和光学材料等领域展现出广阔的应用前景. 目前, 一系列基于氮杂环芳香鎓盐、季铵盐、季鏻盐以及基于柔性烯键和腙键等特定性能的有机盐发光材料被开发出来. 该综述对有机盐发光材料的分子设计、发光原理及其最新研究进展进行了分类总结, 并对该领域的发展进行了展望.

关键词: 有机盐, 发光材料, 进展

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

引用此文

王粉, 王兰婷, 王罡, 钱程, 周映霞, 郑昕. 有机盐发光材料研究进展[J]. 有机化学, 2023, 43(12): 4147-4156.

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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图/表 8

图式1. 含吡啶盐基团的化合物2的合成

Scheme 1. Synthesis of compound 2 containing pyridinium salt group

图式2. 2-苯基-1H-苯并咪唑和苯并咪唑盐10、11和12的合成

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

图式3. 几种噻唑并噻唑桥联咪唑盐14a和15a~15b的合成

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

图式4. 发光剂16的合成路线(a)及通过反复研磨熏蒸或研磨加热下发光剂16在365 nm紫外灯照射下的固态发射颜色变化(b)

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)

图式5. 化合物24的合成

Scheme 5. Synthesis of compound 24

图式6. 化合物25的合成

Scheme 6. Synthesis of compound 25

图式7. 发光季铵盐四甲基溴化铵(28)、十六烷基三甲基溴化铵(30)、十六烷基三甲基氯化铵(31)和十六烷基三乙基碘化铵(32)

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

图式8. 化合物33和34之间的可逆转换

Scheme 8. Reversible conversion between compounds 33 and 34

参考文献 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