Triphenylamine-Based Schiff Base Compounds for the Latent Fingerprints Visualization

doi:10.6023/cjoc202503001

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (11): 4185-4194.DOI: 10.6023/cjoc202503001 Previous Articles Next Articles

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基于三苯胺基席夫碱化合物用于潜指纹可视化的研究

陈发芬^†, 陈春琳^†, 彭智, 张帮翠, 罗海艳, 李杉, 高树林, 王建飞^*(), 李湘广^*(), 杨艳华^*()

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:2025-03-03 修回日期:2025-05-14 发布日期:2025-06-30
作者简介:
^†共同第一作者
基金资助:
国家大学生创新创业计划训练(202411393015); 云南省“兴滇英才支持计划”青年人才专项(ZX20230278); 云南省教育厅科学研究基金(2025Y1050); 国家自然科学基金(22065019); 昆明学院科学研究基金(XPZJ2205); 昆明学院科学研究基金(XPZJ2205-2); 昆明“春城计划”青年拔尖人才(C202014001)

Triphenylamine-Based Schiff Base Compounds for the Latent Fingerprints Visualization

Fafen Chen, Chunlin Chen, Zhi Peng, Bangcui Zhang, Haiyan Luo, Shan Li, Shulin Gao, Jianfei Wang^*(), Xiangguang Li^*(), Yanhua Yang^*()

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

Received:2025-03-03 Revised:2025-05-14 Published:2025-06-30
Contact: *E-mail: wang03507856284@126.com; lixiangguang@iccas.ac.cn; yh_yangkmu@126.com
About author:
^†The authors contributed equally to this work
Supported by:
National College Students? Platform for Innovation and Entrepreneurship Training Program(202411393015); Yunnan Province “Xingdian Talent Supporting Plan” Youth Talent Special Project(ZX20230278); Scientific Research Funds Project of Yunnan Education Department(2025Y1050); National Natural Science Foundation of China(22065019); Scientific Research Funds of Kunming University(XPZJ2205); Scientific Research Funds of Kunming University(XPZJ2205-2); Kunming “Spring City Program” for Youth Top-Notch Talents(C202014001)

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Abstract

To further advance the development of the fluorescent dyes for latent fingerprint imaging, two triphenylamine-based Schiff base compounds containing a benzimidazole group (TPA-BZI) and a phenyl unit (TPA-Ph) were designed and synthesized. Photoluminescence experiments revealed that both compounds exhibited solvatochromism and intramolecular charge transfer (ICT) characteristics in six organic solvents. Additionally, they showed aggregation-induced emission (AIE) in CH₃OH/water mixtures and solid-state fluorescence. These phenomena were further elucidated through time-dependent density functional theory (TD-DFT) calculations. It was also found that the two compounds could be used for latent fingerprints imaging, and could easily distinguish the details of fingerprints from I to III levels, which could provide the preliminary evidence to match personal identification.

Key words: Schiff bases, triphenylamine-based compounds, aggregation-induced emission, latent fingerprints imaging

Cite this article

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.

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Fig. & Tab. 8

Scheme 1. Synthetic routes of two triphenylamine-based salicylaldimine compounds

Figure 1. (a) Normalized absorption spectra and (b) normalized emission spectra of compounds TPA-BZI and TPA-Ph in different organic solvents (c=1×10－5 mol/L, excited at 400 nm), respectively, and (c) the corresponding Lippert-Mataga fitting curves Inset: photos in different organic solvents under 365 nm irradiation

Figure 2. (a) Emission spectra of compounds TPA-BZI and TPA-Ph in CH3OH/H2O mixtures with different fw (c=1×10－5 mol/L, excited at 420 nm), and (b) plots of emission peak intensity versus fw Inset: photos in different fw under 365 nm irradiation

Figure 3. (a) Emission spectra of TPA-BZI and TPA-Ph in the solid states (excited at 420 nm) and (b) their colors under the 80 W lamp and a 365 nm lamp irradiation, respectively

Figure 4. (a) Frontier orbital plots of the HOMO and LUMO energy levels and (b) optimized geometry of the two compounds

Figure 5. Schematic illustration of the fingerprint visualization process with the TPA-BZI developer

Figure 6. Digital photographs of LFPs stained with TPA-BZI and TPA-Ph developers on three substrates: blade, aluminum sheet and tinfoil under irradiation with an 80 W lamp and a 365 nm lamp, respectively

Figure 7. Digital photographs of LFPs stained with (a) TPA-BZI and (b) TPA-Ph developers on the surface of blade under irradiation with a 365 nm lamp, respectively, and enlarged regional images with specific features

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基于三苯胺基席夫碱化合物用于潜指纹可视化的研究

Triphenylamine-Based Schiff Base Compounds for the Latent Fingerprints Visualization

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