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

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 mol/L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, was 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 mol/L, 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 aggregation induced emission luminogen (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, 2024, 44(8): 2571-2580.

Haosen Chang, Liming Yang, Guan Wang, Xinggui Gu. Synthesis of Anthraquinone Derivate with Aggregation-Induced Emission Characteristic for Fingerprint Development[J]. Chinese Journal of Organic Chemistry, 2024, 44(8): 2571-2580.

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图/表 9

图式1. C16-TPA-AQ的合成路线

Scheme 1. Synthetic route of C16-TPA-A

图1. (A)乙腈溶液(c=1×10－5 mol/L)和(B)固体粉末下C16-TPA-AQ的紫外-可见光吸收光谱, 以及C16-TPA-AQ的(C)光致发光光谱和(D)荧光寿命

Figure 1. (A and B) UV-vis absorption spectra for C16-TPA-AQ in acetonitrile solution (c=1×10－5 mol/L) and powder, respectively; (C and D) fluorescence spectra and fluorescence lifetime of C16-TPA-AQ powder Inset shows the fluorescence image of C16-TPA-AQ powder

图2. C16-TPA-AQ的HOMO和LUMO轨道

Figure 2. HOMO and LUMO orbitals of C16-TPA-AQ

图3. (A)化合物C16-TPA-AQ在不同体积分数的甲苯/乙腈混合溶剂的荧光照片、(B)荧光谱图和(C) I/I0曲线

Figure 3. (A) Fluorescence photograph, (B) fluorescence spectra, and (C) I/I0 curve of C16-TPA-AQ in acetonitrile/toluene with different toluene fraction

图4. (A)化合物C16-TPA-AQ分散于不同浓度氯化钾溶液荧光照片、(B)光致发光光谱和(C) I/I0曲线.

Figure 4. (A) Fluorescent photograph, (B) fluorescence spectra, and (C) I/I0 curve of C16-TPA-AQ in KCl solution with different concentration

图5. 含有不同氯化钾浓度的指纹染液粒径分布

Figure 5. Particle distribution of C16-TPA-AQ staining solution with different KCl concentration (A) cKCl=0 mol/L, (B) cKCl=0.09 mol/L, (C) cKCl=0.18 mol/L, (D) cKCl=0.45 mol/L

图 6. (A)玻璃基底、(B)塑料基底、(C)铝箔基底、(D)美工刀片基底上经C16-TPA-AQ染色的指纹荧光图像, 以及(E)在玻璃基底下的指纹细节(1: 短脊线; 2: 湖; 3: 脊毛刺; 4: 脊端点; 5: 脊分叉)

Figure 6. Fluorescence images of fingerprints on (A) glass pane, (B) plastic, (C) aluminum foil, and (D) craft knife blade substrates developed by C16-TPA-AQ, and (E) details on glass substrate (1: short ridge; 2: lake; 3: hook; 4: ridge end; 5: bifurcation)

图7. (A) C16-TPA-AQ染色玻璃基底上陈化5 d的指纹荧光照片、(B)黄线覆盖像素对应的灰度图和(C)指纹细节图

Figure 7. (A) Photograph, (B) greyscale profile image over the yellow line, and (C) details of the fingerprint of 5-days-old fingerprint on glass substrate developed by C16-TPA-AQ

图8. 氯化钾浓度为(A) 0 mol/L, (B) 0.09 mol/L、(C) 0.18 mol/L下的C16-TPA-AQ指纹显影液的玻璃基底上指纹染色效果和(D~F)对应灰度值, 以及(G~I)为指纹微观荧光显微图(点线圈内为汗孔)

Figure 8. Fingerprint stained by C16-TPA-AQ under KCl concentration of (A) 0 mol/L, (B) 0.09 mol/L, (C) 0.18 mol/L, and their corresponding greyscale value graph (D~F); (G~I) fluorescence microscopy of fingerprint with pore details

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