A bifunctional triphenylamine-based fluorescent dye for anti-counterfeiting and latent fingerprint detection

doi:10.6023/cjoc202507001

Chinese Journal of Organic Chemistry Previous Articles Next Articles

ARTICLE

一种用于防伪和潜指纹检测的双功能三苯胺基荧光染料

陈春琳^†, 谭杰^†, 张帮翠, 董官茞, 杨艳华^*, 李湘广^*, 高树林^*

昆明学院化学化工学院云南省金属有机分子材料与器件重点实验室昆明 650214

收稿日期:2025-10-18 修回日期:2025-11-03
基金资助:
国家大学生创新创业计划训练(No. 202411393015), 云南省“兴滇英才支持计划”青年人才专项(No. ZX20230278), 云南省教育厅科学研究基金项目(No. 2025Y1050), 国家自然科学基金(No. 22065019), 昆明学院科学研究基金(No. XPZJ2205, No. XPZJ2205-2), 昆明“春城计划”青年拔尖人才(No. C202014001), 云南省中青年学术技术带头人储备人才项目(No. 202105AC160043)资助项目.

A bifunctional triphenylamine-based fluorescent dye for anti-counterfeiting and latent fingerprint detection

Chen Chunlin, Tan Jie, Zhang Bangcui, Dong Guanchen, Yang Yanhua^*, Li Xiangguang^*, Gao Shulin^*

Yunnan Key Laboratory of Metal-Organic Molecular Materials and Device, School of Chemistry and Chemical Engineering, Kunming University, Kunming 650214

Received:2025-10-18 Revised:2025-11-03
Contact: ^*E-mail: yh_yangkmu@126.com; lixiangguang@iccas.ac.cn; 778144294@qq.com
About author:^†Chen and Tan contributed equally to this article
Supported by:
Project supported by the National College Students’ Platform for Innovation and Entrepreneurship Training Program (No. 202411393015), the Yunnan Province “Xingdian Talent Supporting Plan” Youth Talent Special Project (No. ZX20230278), the Scientific Research Funds Project of Yunnan Education Department (No. 2025Y1050), the National Natural Science Foundation of China (No. 22065019), the Scientific Research Funds of Kunming University (No. XPZJ2205, No. XPZJ2205-2), the Kunming “Spring City Program” for Youth Top-Notch Talents (No. C202014001), the Program for Young and Middle-aged Academic and Technical Leaders Reserve Talents of Yunnan Province (202105AC160043).

1. .pdf(1928KB)

Abstract

To explore the application of multifunctional fluorescent dye, a triphenylamine-based difluoroboron compound with an electron donor-acceptor molecular conformation was designed and successfully synthesized. It is found that it not only has the intramolecular charge transfer characteristics and solvatochromism, but also exhibits aggregation-induced emission performance. These photophysical properties can be well explained by theoretical calculation results. Furthermore, it displays reversible mechanofluorochromism behavior, which originates from phase transition between crystalline and amorphous states, confirmed by powder X-ray diffraction analysis. Leveraging this mechanofluorochromism behavior, the prepared safety paper exhibits anti-counterfeiting characteristics, demonstrating a repeatedly rewritable ink-free writing capability. A developer prepared from a DMSO/H₂O mixture (water content of 60%, c = 1 × 10^-5 mol/L) could visualize latent fingerprint on both non-porous and porous substrates. Further analysis revealed that it could detect the ridge details of fingerprint containing sweat pore from photographs of imaging, which could be applied to personal identification. And latent fingerprint imaging originates from interaction between oleic acid in sweat secretions and dye.

Key words: difluoroboron fluorescent dye, mechanofluorochromism, aggregation-induced emission, anti-counterfeiting, latent fingerprint detection

Cite this article

Chen Chunlin, Tan Jie, Zhang Bangcui, Dong Guanchen, Yang Yanhua, Li Xiangguang, Gao Shulin. A bifunctional triphenylamine-based fluorescent dye for anti-counterfeiting and latent fingerprint detection[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202507001.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

Zhou H.; Gao S.; Weng Z.; Yuna L.; Li W.; Lei P.; Li X.; Yang Y.; Yang, M. Spectrochim. Acta A2025, 333, 125900.
Qian H.; Tian J.; Jiang X.; Zhang B.; Li X.; Yang Y.; Gao S.; Shao L.; Li F. Luminescence2024, 39, e4729.
Qian W.; Zuo M.; Song Y.; Hu X-Y.; Wang, L. Mater. Today Chem.2022, 26, 101115.
Sun H.; Li S.; Liu Q.; Zuo M.; Tian X.; Wang K.; Hu, X-Y. Chinese Chem. Lett.2024, 36, 109999.
Feng Y.; Das P. J.; Young R. M.; Brown P. J.; Hornick J. E.; Weber J. A.; Seale J. S. W.; Stern C. L.; Wasielewski M. R.; Stoddart, J. F. J. Am. Chem. Soc.2022, 144, 16841.
Cao Y.; Wang X.; Shi X.; Clee S. M.; McGeer P. L.; Wolf M. O.; Orvig, C. Angew. Chem. Int. Ed.2017, 56, 15603.
Feng X.; Zhou N.; Zhou H.; Song F.; Fu S.; Zhang W.; Liu X.; Xu, D. New J. Chem.2022, 46, 15657.
Jia M.; Hu H.; Xiong X.; Lyu L.; Zhao H.; Zhang S.; Hou J. Dyes Pigm.2021, 190, 109343.
Gac A. L.; Mallet-Ladeira S.; Roger J.; Hierso J.-C.; Miqueu K.; Bouhadir G.; Bourissou, D. Angew. Chem. Int. Ed.2025, 64, e202501178.
Yin Y.; Guan Q.; Chen Z.; Deng D.-D.; Liu S.; Sun Y.; Liu, S. L. Sci. Adv.2024, 10, adk5444.
Wang Q.; Li D.; Zhang Z.; Shen L.; Xu H.; Wang Z.; Redshaw C.; Zhang, Q. Spectrochim. Acta A2025, 330, 125694.
Xu M.; Tian J.; Yang Y.; Gou G.; Li F.; Shao L.; Chi, K. Chinese J. Org. Chem.2023, 43, 1824.
Zhu H.; Weng S.; Zhang H.; Yu H.; Kong L.; Zhong Y.; Tian Y.; Yang J. CrystEngComm2018, 20, 2772.
Yang S.; Tan S.; Chen Y.; Tian J.; Yang Y.; Li X.; Gao S. Dyes Pigm.2023, 220, 111736.
Yang R.; Li L.; Gao S.; Weng Z.; Li W.; Wang Z.; Li X.; Yang Y.; Jiang, W. J. Org. Chem.2025, 90, 6044.
Zhang C.; Gao X.; Ma D.; Zou D.; Zhang N.; Yan J. Dyes Pigm.2024, 227, 112180.
Sun J.; Qian C.; Xu S.; Jia X.; Zhai L.; Zhao J.; Lu, R. Org. Biomol. Chem.2018, 16, 7438.
Luo H.; Chen C.; Li S.; Zhang B.; Chen F.; Tian J.; Gao S.; Wang J.; Li X.; Yang, Y. New J. Chem.2025, 49, 7414.
Choi N.-E.; Kim E.-J.; Lee J. RSC Adv.2022, 12, 33180.
Song Y.; Sun J.; Sun M.; Simalou O.; Gao H.; Peng J.; Shu Y.; Zhai L.; Lu R. Opt. Mater.2021, 115, 111006.
Tian R.; Yu Q.; Mei L.-J.; Zhu F.-Y.; Qin Q.; Ma R.; Wang Y.-L.; Li C.; Zhu, M.-Q. Sensor. Actuat. B-Chem.2023, 396, 134634.
Duan L.; Zheng Q.; Tu T. Adv. Mater.2022, 34, 2202540.
Liu D.; Wang M.; Han J.; Zhang Z.; Wang, X. Sensor. Actuat. B-Chem.2024, 401, 135045.
Chen C.; Tian J.; Li S.; Gao S.; Yang Y.; Li X.; Zhang, J. J. Photochem. Photobio. A2025, 460, 116125.
Tan S.; Tian J.; Yang S.; Zhang B.; Yang Y.; Li X.; Gao S. J. Lumin.2024, 275, 120730.
Zhang B.; Chen C.; Tian J.; Gao S.; Yang Y.; Li X.; Zhang, J. New J. Chem.2024, 48, 20399.
Tian J.; Su Z.; Jiang X.; Zhang B.; Yang Y.; Li X.; Gou, G. Spectrochim. Acta A2024, 319, 124568.
Chen Y.; Zhou Y.; Wang Z.; Wang M.; Gao W.; Zhou Y.; Liu M.; Huang X.; Wu H. CrystEngComm2019, 21, 4258.
Zhou L.; Xu D.; Gao H.; Han A.; Yang Y.; Zhang C.; Liu X.; Zhao F. RSC Adv.2016, 6, 69560.
Li S.; Wang L.; Ma Y.; Zhu L.; Lin, W. Sensor. Actuat. B-Chem.2022, 371, 132595.
Mei J.; Hong Y.; Lam J. W. Y.; Qin A.; Tang Y.; Tang, B. Z. Adv. Mater.2014, 26, 5429.
Gao B.; Wang H.; Hao Y.; Fu L.; Fang H.; Jiang Y.; Wang L.; Chen Q.; Xia H.; Pan L.; Ma Y.; Sun, H. J. Phys. Chem. B2010, 114, 128.
Yu C.; Hao E.; Fang X.; Wu Q.; Wang L.; Li J.; Xu. L.; Jiao L.; Wong, W. J. Mater. Chem. C2019, 7, 3269.
Huang G.; Xia Q.; Huang W.; Tian J.; He Z.; Li B. S.; Tang, B. Z. Angew. Chem. Int. Ed.2019, 58, 17814.
Liu, M.; Han, Y.; Yuan, W.; Guo, C.; Shi, S.; Liu, X.; Chen. Y. Dalton Trans. 2019, 48, 14626.
Jin X.; Xin R.; Wang S.; Yin W.; Xu T.; Jiang Y.; Ji X.; Chen L.; Liu, J. Sensor. Actuat. B-Chem.2017, 244, 777.
Jiang Q.; Tian J.; Peng Z.; Gao S.; Wang J.; Li X.; Yang Y. ChemistrySelect2025, 10, e202500742.
Tian J.; Du Y.; Chen C.; Li X.; Gao S.; Yang Y.; Jiang S. Forensic Chem.2025, 42, 100643.
Luo Y.Guidance for Criminal Science and Technology Experiments, China People's Public Security University Press, Beijing, 2017, pp. 63~64.
Liu L.; Wang J.; Wang X.; Wang H.; Li M.; Wu T.; Gao G.; Zheng X.; Liu G.; Fan L.; Shen W.; Ru G.; Zhao Z.; Tang, B. Z. Chinese J. Chem.2023, 41, 1465.
Zhang M.; Zhang J.; Zhang Z.; Kwok R. T.K.; Lam J. W. Y.; Jia G.; Tang, B. Z. Adv. Opt. Mater.2024, 12, 2302781.
Du Y.; Tian J.; Jiang X.; Chen C.; Yang Y.; Gao S. ChemistrySelect2024, 9, e202402064.

[1]	Fafen Chen, Chunlin Chen, Zhi Peng, Bangcui Zhang, Haiyan Luo, Shan Li, Shulin Gao, Jianfei Wang, Xiangguang Li, Yanhua Yang. Triphenylamine-Based Schiff Base Compounds for the Latent Fingerprints Visualization [J]. Chinese Journal of Organic Chemistry, 2025, 45(11): 4185-4194.
[2]	Yang Zhao, Panpan Chen, Gaonan Li, Zhigang Niu, Enju Wang. Tetraarylimidazole-Based Aggregation-Induced Emission Luminogens and Their Cell-Imaging Application [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2156-2162.
[3]	Sihong Chen, Jiamin Xu, Yuemei Li, Baoru Peng, Lingyu Luo, Huiye Feng, Zhaohua Chen, Zhaoyang Wang. Research Progress of Aggregation-Caused Quenching (ACQ) to Aggregation-Induced Emission (AIE) Transformation Based on Organic Small Molecules [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1651-1666.
[4]	Junhui Jia, Juanjuan Wen. Mechanoﬂuorochromic Luminescence, and Al³⁺ Detection of an Aggregation-Induced Emission-Active Salicylaldehyde-Based Acylhydrazone Derivative [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1728-1733.

一种用于防伪和潜指纹检测的双功能三苯胺基荧光染料

A bifunctional triphenylamine-based fluorescent dye for anti-counterfeiting and latent fingerprint detection

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 4

Recommended Articles

Metrics

Comments