具有聚集诱导发光特性的蒽醌衍生物的合成及其指纹显影应用

doi:10.6023/cjoc202403045

研究论文

具有聚集诱导发光特性的蒽醌衍生物的合成及其指纹显影应用

常淏森^a, 杨黎明^a, 王冠^a,*, 顾星桂^a,*

^a北京化工大学软物质工程与高精尖中心, 化工资源工程国家重点实验室, 材料科学与工程学院, 北京化工大学, 北京, 100029 中华人民共和国

收稿日期:2024-03-28 修回日期:2024-05-20
基金资助:
国家自然科学基金 (No. 52173154, 22375014 和 52373171)资助项目.

Synthesis of Anthraquinone Derivate with Aggregation-Induced Emission Characteristic for Fingerprint Development

Chang Haosen^a, Yang Liming^a, Wang Guan^a,*, Gu Xinggui^a,*

^aBeijing Advanced Innovation Center for Soft Matter Science and Engineering, State Key Laboratory of Chemical Resource Engineering, College of Materials Science and Engineering, Beijing University of Chemical Technology, Beijing, 100029 China

Received:2024-03-28 Revised:2024-05-20
Contact: * E-mail: guxinggui@mail.buct.edu.cn, wangguan@mail.buct.edu.cn
Supported by:
National Natural Science Foundation of China (No. 52173154, 22375014, and 52373171).

文章分享

1. cjoc202403045辅助材料.doc(6890KB)

摘要/Abstract

以蒽醌作为电子受体, 三苯胺作为电子给体, 经过表面活性剂修饰, 得到了一种新型可用于指纹显影剂的表面活性剂有机功能分子C16-TPA-AQ. 该分子在聚集态下发射红色荧光, 具有显著的聚集诱导发光效应. 将其制成了指纹染液, 并通过氯化钾浓度调控聚集程度. 结果表明, 该染液对于附着于不同基底的指纹均有良好的显影效果; 在 0.18 M氯化钾调控下, 得到了三级指纹结构. 此外,该染液对陈旧指纹也具有显影效果. 由此可见,该材料在指纹显影领域具有一定应用前景.

关键词: 聚集诱导效应, 蒽醌, 表面活性剂, 指纹显影

An interesting surfactant anthraquinone derivative, named as C16-TPA-AQ, is prepared for fingerprint development by symmetrically introducing strong electron-donating triphenylaniline units. C16-TPA-AQ exhibits significant aggregation-induced emission with red fluorescence in the aggregated state, which could be used to prepare fingerprint developer with its aggregation effectively controlled by potassium chloride concentration. Such developer exerts excellent development effect on fingerprints settled on different substrates with almost no influence of background. By tuning the concentration of potassium chloride to be 0.18 M, level 3 fingerprint details are successfully obtained due to micelle formation and demulsification of surfactants. Besides, the developer is also effective on aged fingerprints. This finding demonstrates the potential of red-emission and surfactant AIEgen in latent fingerprint development.

Key words: aggregation-induced emission, anthraquinone, surfactant, fingerprint development

引用此文

常淏森, 杨黎明, 王冠, 顾星桂. 具有聚集诱导发光特性的蒽醌衍生物的合成及其指纹显影应用[J]. 有机化学, doi: 10.6023/cjoc202403045.

Chang Haosen, Yang Liming, Wang Guan, Gu Xinggui. Synthesis of Anthraquinone Derivate with Aggregation-Induced Emission Characteristic for Fingerprint Development[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202403045.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1]Hazarika, P.; Russell, D. A. Angew. Chem. Int. Ed. 2012, 51, 3524.
[2]Chen Y.; Li A.; Li X.; Tu L.; Xie Y.; Xu S.; Li Z. Adv. Mater.2023, 35, 2211917.
[3]Zou, R.; Yu, Y.; Pan, H.; Zhang, P.; Cheng, F.; Zhang, C.; Chen, S.; Chen, J.; Zeng, R.ACS Appl. Mater. Inter. 2022, 14, 16746.
[4]Malik A. H.; Kalita A.; Iyer, P. K. ACS Appl. Mater. Interfaces.2017, 9, 37501.
[5]Huang H.; Zhou Y.; Wang M.; Zhang J.; Cao X.; Wang S.; Cao D.; Cui, C. Angew. Chem. Int. Ed.2019, 58, 10132.
[6]Suresh R.; Thiyagarajan S. K.; Ramamurthy, P. Sens. Actuators B Chem.2018, 258, 184.
[7]Jung H. S.; Cho K. J.; Ryu S. J.; Takagi Y.; Roche P. A.; Neuman, K. C. ACS Appl. Mater. Interfaces.2020, 12, 6641.
[8]Hansen D. B.; Joullié, M. M. Chem. Soc. Rev.2005, 34, 408.
[9]Bi X.; Shi Y.; Peng T.; Yue S.; Wang F.; Zheng L.; Cao, Q. E. Adv. Funct. Mater.2021, 31, 2101312.
[10]Haque F.; Westland A. D.; Milligan J.; Kerr, F. M. Forensic Sci. Int.,1989, 41, 73.
[11]Bijl L. J.; Theeuwen, A. B. Arch. Kriminol.1983, 172, 93.
[12]Keating D. M.; Miller, J. J. J. Forensic Sci.1993, 38, 197
[13]Datta, A. K. In Advances in Fingerprint Technology, Vol. 3, Eds.: Lee, H. C.; Gaensslen, R., CRC Press, Boca Raton, 2001, p. 136.
[14]Wang R.; Huang Z.; Ding L.; Yang F.; Peng, D. ACS Appl. Nano Mater.2022, 5, 2214.
[15]Duan L.; Zheng Q.; Tu T. Adv. Mater.2022, 34, 2202540.
[16]Chen J.; Wei J. S.; Zhang P.; Niu X. Q.; Zhao W.; Zhu Z. Y.; Ding H.; Xiong, H. M. ACS Appl. Mater. Interfaces.2017, 9, 18429.
[17]Chen, J.; Li, M.; Sun, R.; Xie, Y.; Reimers, J. R.; Sun, L.Adv. Funct. Mater. 2024, 2315726.
[18]Xu J.; Zhang B.; Jia L.; Fan Y.; Chen R.; Zhu T.; Liu, B. ACS Appl. Mater. Interfaces.2019, 11, 35294.
[19]Ruan, N.; Qiu Q.; Wei X.; Liu, J.; Wu, L.; Jia, N.; Huang, C.; James, T. D.J. Am. Chem. Soc. 2024, 146, 2072.
[20]Lian J.; Meng F.; Wang W.; Zhang Z. Front. Chem.2020, 8, 594864.
[21]Li L.; Ma H.; Zhang J.; Zhao E.; Hao J.; Huang H.; Li P.; Gu X.; Tang, B.-Z. J. Am. Chem. Soc.2021, 143, 3856.
[22]Feng G.; Liu, B. Acc. Chem. Res.2018, 51, 1404.
[23]Thomas S. W.; Joly G. D.; Swager, T. M. Chem. Rev.2007, 107, 1339.
[24]Yuan, L.; Lin, W.; Yang, Y.; Chen, H.J. Am. Chem. Soc. 2012, 134, 1200.
[25]Xiao T.; Zhang L.; Chen D.; Zhang Q.; Wang Q.; Li Z.-Y.; Sun, X.-Q. Org. Chem. Front.2023, 10, 3245.
[26]Seite S.; Zucchi H.; Moyal D.; Tison S.; Compan D.; Christiaens F.; Gueniche A.; Fourtanier, A. Brit. J. Dermatol.2003, 148, 291.
[27]Hong, Y.; Lam, J. W. Y.; Tang, B.-Z.2[27]Hong, Y.; Lam, J. W. Y.; Tang, B.-Z.Chem. Commun. 2009, 4332.
[28]Gui Y.; Chen K.; Sun Y.; Tan Y.; Luo W.; Zhu D.; Xiong, Y. Chin. J. Chem.2022, 41, 1249.
[29]Duan L.; Zheng Q.; Tu T. Adv. Mater.2022, 34, 2202540.
[30]Zhou P.; Han K. Aggregate.2022, 3, e160.
[31]Zhao Y.; Zhang X.; Yang Y.; Zhu L.; Zhou, Y. Acta. Chim. Sinica.2024, 82, 265 (in Chinese).
(赵玉强, 张霞, 杨芸如, 朱立平, 周莹. 化学学报, 2024, 82, 265.)
[32]Hu J.; Jiang W.; Yuan L.; Duan C.; Yuan Q.; Long Z.; Lou X. Aggregate.2021, 2, 48.
[33]Guo X.; Yuan P.; Fan J.; Qiao X.; Yang D.; Dai Y.; Sun Q.; Qin A.; Tang B.-Z.; Ma D. Adv. Mater.2021, 33, 2006953.
[34]Zhang Y.; Nie F.; Zhou L.; Wang X.; Liu Y.; Huo Y.; Chen W.; Zhao, Z. Chin. J. Org. Chem.2023, 43, 3876 (in Chinese).
(张越华, 聂飞, 周路, 王晓烽, 刘源, 霍延平, 陈文铖, 赵祖金, 有机化学, 2023, 43, 3876.)
[35]Zeng C.; Hu P.; Wang B.; Fang W.; Zhao, K. Chin. J. Org. Chem.2023, 43, 3287 (in Chinese).
(曾崇洋, 胡平, 汪必琴, 方文彦, 赵可清, 有机化学, 2023, 43, 3287.)
[36]Feng L.; Li C.; Liu L.; Wang Z.; Chen Z.; Yu J.; Ji W.; Jiang G.; Zhang P.; Wang J.; Tang B.-Z. ACS Nano.2022, 16, 4162.
[37]Wu J.; Liu W.; Ge J.; Zhang H.;Wang, P. Chem. Soc. Rev.2011, 40, 3483.
[38]Guo J.; Dai J.; Peng X.; Wang Q.; Wang S.; Lou X.; Xia F.; Zhao Z.; Tang B.-Z. ACS Nano.2021, 15, 20042.
[39]Zhang Q.; Kuwabara H.; Potscavage Jr W. J.; Huang S.; Hatae Y.; Shibata T.; Adachi, C. J. Am. Chem. Soc.2014, 136, 18070.
[40]Yang Y.; Zhao L.; Wang S.; Ding J.; Wang L. Macromolecules.2018, 51, 9933.
[41]Jiang G.; Yu J.; Wang J.; Tang B.-Z. Aggregate.2022, 3, e285.
[42]Yu D.; Huang X.; Deng M.; Lin Y.; Jiang L.; Huang J.; Wang, Y. J. Phys. Chem. B.2010, 114, 14955.
[43]Cadd S.; Islam M.; Manson P.; Bleay S. Sci. Justice.2015, 55, 219.
[44]Liu Z.; Zhao G.; Brewer M.; Lv Q.; Sudhölter, E. Jr. Adv. Colloid Interface Sci.2021, 294, 102467.
[45]Mushtaq, M.; Al-Shalabi, E. W.; AlAmeri, W.Geoenergy Sci. Eng. 2023, 230, 212243.
[46]Grenoble Z.; Trabelsi, S. Adv. Colloid Interface Sci.2018, 260, 32.