Pyridine-Induced Multifunctional Fluorescent Probes for Latent Fingerprint Imaging and Photoprinting Applications

doi:10.19894/j.issn.1000-0518.250190

Chinese Journal of Applied Chemistry ›› 2026, Vol. 43 ›› Issue (1): 67-76.DOI: 10.19894/j.issn.1000-0518.250190

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Pyridine-Induced Multifunctional Fluorescent Probes for Latent Fingerprint Imaging and Photoprinting Applications

Cong ZENG¹^,²^,³, Jia-Long HU¹^,²^,³, Shi-Yu FENG¹^,²^,³(), Wei-Guo HUANG¹^,²^,³()

^1.College of Chemistry，Fuzhou University，Fuzhou 350108，China
^2.State Key Laboratory of Structural Chemistry，Fujian Institute of Research on the Structure of Matter，Chinese Academy of Sciences，Fuzhou 350002，China
^3.Fujian College，University of Chinese Academy of Sciences，Fuzhou 350002，China

Received:2025-05-09 Accepted:2025-09-30 Published:2026-01-01 Online:2026-01-26
Contact: Shi-Yu FENG,Wei-Guo HUANG
About author:whuang@fjirsm.ac.cn
fengshiyu@fjirsm.ac.cn
Supported by:
the Natural Science Foundation of Fujian Province(2024J09055)

Abstract

Abstract:

A pyridine-containing heterocyclic fluorescent probe， N，N-diphenyl-4-（pyridin-4-yl）aniline （TPA-Py）， with a D-π-A architecture， along with its amphiphilic derivative 1-（2-Hydroxyethgl）-4-［4-（diphenylamine）phenyl］pyridin-1-ium （TPA-PyBr）， was synthesized， and their photophysical properties were systematically investigated. The experimental results demonstrated that TPA-Py exhibits pronounced acidochromic behavior， with its fluorescence emission peaks shifting from 415 nm to 550 nm upon protonation of the pyridyl group. Furthermore， TPA-Py exhibits fluorescence color changes in response to polar matrices， showing a remarkable bathochromic shift of over 160 nm as the concentration of poly（pentafluorophenyl acrylate）（pPFPA） increases. Compared with TPA-Py， TPA-PyBr exhibits improved aqueous solubility and aggregation-induced emission （AIE） behavior. This enables TPA-PyBr to achieve high-contrast fluorescent imaging of latent fingerprints in purely aqueous media by selectively targeting lipid-rich microdomains through hydrophobic interactions， thereby overcoming issues of biological sample degradation caused by organic solvent dependency in conventional probes. In addition， the TPA-Py-doped poly（methyl methacrylate）（PMMA） film achieves photoactivable room-temperature phosphorescence， showcasing its capability for erasable optical printing. This work explores the multifunctional capabilities of pyridine-based fluorescent probes in applications such as acid-responsive sensing， microenvironment monitoring， fingerprint visualization， and optical printing， providing valuable insights for the development of intelligent， responsive optoelectronic materials.

Key words: Acidochromic behavior, Microenvironment monitoring, Room-temperature phosphorescence, Aggregation-induced emission, Fingerprint visualization

CLC Number:

O626.3

Cong ZENG, Jia-Long HU, Shi-Yu FENG, Wei-Guo HUANG. Pyridine-Induced Multifunctional Fluorescent Probes for Latent Fingerprint Imaging and Photoprinting Applications[J]. Chinese Journal of Applied Chemistry, 2026, 43(1): 67-76.

Figures/Tables 7

Fig.1 （A） Emission and absorption spectra of TPA-Py and TPA-PyBr；（B） Absorption spectra of TPA-Py at varying acid concentrations；（C） Emission spectra and fluorescence images of TPA-Py at varying acid concentrations

Fig.2 （A） Absorption spectra of TPA-Py in toluene as a function of pPFPA concentration；（B） Emission spectra of TPA-Py in toluene as a function of pPFPA concentration， along with the corresponding fluorescence images

Fig.3 （A） Absorption and （B） emission spectra of TPA-Py in methanol/water mixtures with varying water fractions；（D） Absorption and （E） emission spectra of TPA-PyBr in water/THF mixtures with varying THF fractions. Plots of relative fluorescence intensity （I/I0） versus φw and φTHF at different emission wavelengths for （C） TPA-Py and （F） TPA-PyBr

Fig.4 Schematic diagram of the fingerprint visualization mechanism and fluorescence images of fingerprints developed with different developing agents on aluminum foil

Fig.5 Photoactivable RTP phenomenon of TPA-Py@PMMA film

Fig.6 Erasable photoprinted phosphorescent patterns of TPA-Py@PMMA films

References 32

[1]	SHEN Y， LE X X， WU Y， et al. Stimulus-responsive polymer materials toward multi-mode and multi-level information anti-counterfeiting： recent advances and future challenges［J］. Chem Soc Rev， 2024， 53（2）： 606-623.
[2]	DONG Y， FENG S Y， HUANG W G， et al. Algorithm in chemistry： molecular logic gate-based data protection［J］. Chem Soc Rev， 2025， 54（8）： 3681-3735.
[3]	HUANG W， FENG S Y， LIU J， et al. Configuration-induced multichromism of phenanthridine derivatives： a type of versatile fluorescent probe for microenvironmental monitoring［J］. Angew Chem Int Ed， 2023， 62（9）： e202219337.
[4]	陈虹蓉，伍亚男，陈仕焰，等. 2-羟基萘甲醛苯甲酰腙衍生物对Al³⁺的裸眼识别和荧光传感［J］. 应用化学， 2016， 33（5）： 599-605.
	CHEN H R， WU Y N， CHEN S Y， et al “Naked-eye” and fluorescence “turn-on” recognition of Al³⁺ based on 2-hydroxy-naphthalene-formaldehyde benzoyl-hydrazone derivatives［J］. Chin J Appl Chem， 2016， 33（5）： 599-605.
[5]	周佳，倪赟，张承武，等. 嘧啶基双光子荧光染料的设计合成与生物成像［J］. 应用化学， 2017， 34（12）： 1450-1456.
	ZHOU J， NI B， ZHANG C W， et al. Design and synthesis of pyrimidine based two-photon fluorescence probe and its application in bioimaging［J］. Chin J Appl Chem， 2017， 34（12）： 1450-1456.
[6]	KUMAR A P， JIN D， LEE Y I. Recent development on spectroscopic methods for chiral analysis of enantiomeric compounds［J］. Appl Spec Rev， 2009， 44（4）： 267-316.
[7]	IM H， YOON J， CHOI J， et al. Chaotic organic crystal phosphorescent patterns for physical unclonable functions［J］. Adv Mater， 2021， 33（44）： 2102542.
[8]	JI Y M， LIU G J， LI C Y， et al. Water soluble glucosamine-coated AIE active fluorescent organic nanoparticles： design， synthesis and assembly for specific detection of heparin based on carbohydrate-carbohydrate interactions［J］. Chem Asian J， 2019， 14（19）： 3295-3300.
[9]	CHAI X Y， ZHU W W， MENG Q G， et al. Si-rhodamine based water-soluble fluorescent probe for bioimaging of Cu⁺［J］. Chin Chem Lett， 2021， 32（1）： 210-213.
[10]	QIAN Y X， LIU H M， TAN H J， et al. A novel water-soluble fluorescence probe with wash-free cellular imaging capacity based on AIE characteristics［J］. Macromol Rapid Commun， 2017， 38（10）： 1600684.
[11]	高长江，黄鑫，田亚洋，等. 一种近红外快速响应型硫化氢荧光探针的合成及细胞成像［J］. 应用化学， 2025， 42（2）： 192-200.
	GAO C J， HUANG X， TIAN Y Y， et al. Synthesis and cell imaging of a near-infrared fast responsive hydrogen sulfide fluorescent probe［J］. Chin J Appl Chem， 2025， 42（2）： 192-200.
[12]	蔡丰泽，徐永玲，周乐，等. 一种红光发射的粘度荧光探针［J］. 应用化学， 2020， 37（4）： 440-446.
	CAI F Z， XU Y L， ZHOU L， et al. Synthesis and properties of red-emitting fluorescence probe for viscosity detection［J］. Chin J Appl Chem， 2020， 37（4）： 440-446.
[13]	MITRA A， RAMANUJAM B， RAO C P. 1-（D-Glucopyranosyl-2′-deoxy-2′-iminomethyl）-2-hydroxynaphthalene as chemo-sensor for Fe³⁺ in aqueous HEPES buffer based on colour changes observable with the naked eye［J］. Tetra Lett， 2009， 50（7）： 776-780.
[14]	ERDEMIR S， MALKONDU S. Visual and quantitative detection of CN^- ion in aqueous media by an HBT-Br and thiazolium conjugated fluorometric and colorimetric probe： real samples and useful applications［J］. Talanta， 2021， 221（1）： 121-639.
[15]	LIU Y， MENG F F， LIN W Y. Single fluorescent probe for reversibly detecting copper ions and cysteine in a pure water system［J］. RSC Adv， 2016， 6（37）： 30951-30955.
[16]	ZHANG Q J， LIAO M Y， XIAO K R， et al. A water-soluble fluorescence probe based on perylene diimide for rapid and selective detection of perfluorooctane sulfonate in 100% aqueous media［J］. Sens Actuators B， 2022， 350： 130851.
[17]	YANG Q Z， WEN Y J， XU J， et al. An HBT-based fluorescent dye with enhanced quantum yield in water system and its application for constructing NQO1 fluorescent probe［J］. Talanta， 2020， 216： 120982.
[18]	ZUO M D， ZENG C， LIU J， et al. Pyridine-based rigidochromic fluorescent security ink［J］. Chin J Chem， 2025， 43（12）： 1405-1416.
[19]	CHEN Y Y， CHEN J M， WU H C， et al. Dynamically securing the data by ¹O₂ sensitization of fluorescent composites with a high latency and uncrackable features［J］. Chin J Chem， 2024， 42（14）： 1651-1658.
[20]	HE B Z， HUANG J C， ZHANG J， et al. In-situ generation of poly（quinolizine）s via catalyst-free polyannulations of activated diyne and pyridines［J］. Sci China Chem， 2022， 65（4）： 789-795.
[21]	LETHESH K C， EVJEN S， RAJ J J， et al. Hydroxyl functionalized pyridinium ionic liquids： experimental and theoretical study on physicochemical and electrochemical properties［J］. Front Chem， 2019， 7： 625.
[22]	CHEN G， LI W B， ZHOU T R， et al. Conjugation-induced rigidity in twisting molecules： filling the gap between aggregation-caused quenching and aggregation-induced emission［J］. Adv Mater， 2015， 27（30）： 4496-4501.
[23]	CHEN S， HUANG W， YANG K， et al. Constructing versatile hydrophilic surfaces via in-situ aminolysis［J］. Chin J Struct Chem， 2021， 40（11）： 1525-1534.
[24]	FENG S Y， ZHU L J， WANG D H， et al. Rigidity-tuned full-Color emission： uncommon luminescence change from polymer free-volume variations［J］. Adv Mater， 2022， 34（24）： 2201337.
[25]	LING Y， LIU J， DONG Y， et al. Conventional non-fluorescent polymers： unconventional security inks for data storage and multidimensional photonic cryptography［J］. Adv Mater， 2023， 35（39）： 2303641.
[26]	DONG Y， WU H C， LIU J， et al. Multicolor photochemical printing inside polymer matrices for advanced photonic anticounterfeiting［J］. Adv Mater， 2024， 36（26）： 2401294.
[27]	CHEN J M， CHEN Y Y， LIU J， et al. In Situ optical detection of amines at a parts-per-quadrillion level by severing the through-space conjugated supramolecular domino［J］. J Am Chem Soc， 2024， 146（4）： 2604-2614.
[28]	CHEN Y， LI A S， LI X N， et al. Multi-stimuli-responsive amphiphilic pyridinium salt and its application in the visualization of level 3 details in latent fingerprints［J］. Adv Mater， 2023， 35（20）： 2401294.
[29]	陈艳，张春静，高东梅，等.潜指纹显现方法研究进展［J］. 应用化学， 2011， 28（10）： 1099-1107.
	CHEN Y， ZHANG C J， GAO D M， et al. Development of visualization of latent fingerprints［J］. Chin J Appl Chem， 2011， 28（10）： 1099-1107.
[30]	李冲，陈颖，谢诺华，等. 亲水性二芳基乙烯荧光分子开关的研究进展［J］. 应用化学， 2017， 34（12）： 1379-1402.
	LI C， CHEN Y， XIE N H， et al. Research progress on hydrophilic photoswitchable fluorescent diarylethenes［J］. Chin J Appl Chem， 2017， 34（12）： 1379-1402.
[31]	XIONG S D， XIONG Y， WANG D L， et al. Achieving tunable organic afterglow and UV-irradiation-responsive ultralong room-temperature phosphorescence from pyridine-substituted triphenylamine derivatives［J］. Adv Mater， 2023， 35（28）： 2301874.
[32]	MA F L， WU B， ZHANG S W， et al. Lone pairs-mediated multiple through-space interactions for efficient room-temperature phosphorescence［J］. J Am Chem Soc， 2025， 147（12）： 10803-10814.

Pyridine-Induced Multifunctional Fluorescent Probes for Latent Fingerprint Imaging and Photoprinting Applications

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