双亲性噻吩羧酸衍生物的制备及潜指纹检测应用
作者:
作者单位:

南京工业大学 化学与分子工程学院

中图分类号:

O69

基金项目:

江苏省自然科学基金(BK20220351);江苏省高等学校基础科学研究项目(22KJB150027);大学生创新创业训练计划项目(202310291310T,2023DC0829)


Preparation of amphiphilic thienyl carboxylic acid derivatives and application for latent fingerprint detection
Author:
Affiliation:

School of Chemistry and Molecular Engineering,Nanjing Tech University

  • 摘要
  • | |
  • 访问统计
  • |
  • 参考文献 [26]
  • |
  • 相似文献 [20]
  • | | |
  • 文章评论
    摘要:

    5-溴噻吩-2-羧酸和(4-(二苯基氨基)苯基)硼酸通过Suzuki偶联反应,合成双亲性噻吩羧酸衍生物5-(4-(二苯基氨基)苯基)噻吩-2-羧酸及其钾盐(TTC-H和TTC-K)。在结构表征的基础上,利用紫外-可见光吸收光谱,荧光发射光谱系统讨论了目标分子及其聚集态的光物理性质。通过密度泛函理论计算和溶剂化显色效应,进一步验证了分子内存在电荷转移特性。晶体结构解析及Hirshfeld表面分析表明,TTC-H分子间存在C…H (31.6%)和O…H (14.6%)氢键等弱相互作用力。TTC-H与TTC-K均具有聚集诱导发光性质。TTC-K因具有羧酸盐结构,表现出更好的水溶性,将其水溶液通过化学浸渍法和雾化法应用于潜指纹成像,均可精确高效地得到指纹的3级结构。TTC-K水溶液试剂能在低浓度下(1×10-4 mol/L)实现对潜指纹的快速识别(< 5 s),陈化稳定性好,对于陈旧指纹(< 14天)也具有良好的成像效果。

    Abstract:

    The amphiphilic carboxylic acid derivatives, 5-[(4-(diphenylamino)phenyl)]thiophen-2-carboxylic acid and its potassium salts (TTC-H and TTC-K), were synthesized through a Suzuki coupling reaction involving 5-bromothiophen-2-carboxylic acid and [(4-(diphenylamino)phenyl)]boric acid. The structures of the two compounds were characterized by 1HNMR and 13CNMR. The UV-Vis absorption spectroscopy was used to verify the photophysical properties of TTC-H and TTC-K, while fluorescence emission spectroscopy systematically discussed their aggregated states. Density-functional theory calculations and solvation colorimetric effects confirmed the charge transfer properties within the molecules of TTC-H and TTC-K. Their crystal structures were resolved and analyzed by Hirshfeld surface analysis, and the results showed that there were weak interaction forces between TTC-H molecules, such as C···H (31.6%, accounting for the percentage of the total interaction force, similarly hereinafter), H···H (44.6%) and O···H (14.6%). Both TTC-H and TTC-K possessed the property of aggregation-induced emission (AIE). The aqueous solution of TTC-K was proved effective in revealing the tertiary structure of latent fingerprints through chemical impregnation and atomization methods with a good stability of aging. And even at low concentrations (5×10-5 mol/L), the TTC-K aqueous solution reagent enabled rapid identification of latent fingerprints (≤5 s) by chemical impregnation method. And both old fingerprints (≤14 d) and fingerprints soaked in water (≤7 d) have good imaging effects.

    参考文献
    [1] ZHANG Y Y, ZHOU W, XUE Y, et al. Multiplexed imaging of trace residues in a single latent fingerprint[J]. Analytical Chemistry, 2016, 88(24): 12502-12507. DOI:10.1021/acs.analchem.6b04077.
    [2] CHEN S J, JIA K, FANG Y, et al. Highly emissive dimethylamino naphthalenyl phenylethene derivatives for visualization of latent fingerprints and imaging of lysosomes[J]. Dyes and Pigments, 2022, 205: 110534. DOI:10.1016/j.dyepig.2022.110534.
    [3] WANG M, LI M, YU A, et al. Fluorescent nanomaterials for the development of latent fingerprints in forensic sciences[J]. Advanced Functional Materials, 2017, 27(14): 1606243. DOI:10.1002/adfm.201606243.
    [4] SINGH P, SINGH H, SHARMA R, et al. Diphenylpyrimidinone–salicylideneamine – new ESIPT based AIEgens with applications in latent fingerprinting[J]. Journal of Materials Chemistry C, 2016, 4(47): 11180-11189. DOI:10.1039/C6TC03701A.
    [5] LIU R, SONG Z M, LI Y, et al. An AIPE-active heteroleptic Ir(III) complex for latent fingermarks detection[J]. Sensors and Actuators B: Chemical, 2018, 259: 840-846. DOI:10.1016/j.snb.2017.12.122.
    [6] SONG Z M (宋忠明), PANG Y D (庞玉东), MAO Y Y (毛月圆), et al. Blue emitting 3-bromo-5-pyrazolamide material with aggregation-induced emission for latent fingerprint detection[J]. Fine Chemicals (精细化工), 2023,40(6): 1032.
    [7] LUO J D, XIE Z L, LAM J W Y, et al. Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole[J]. Chemical Communications, 2001(18): 1740-1741. DOI:10.1039/b105159h.
    [8] LI Y, XU L, SU B. Aggregation induced emission for the recognition of latent fingerprints[J]. Chemical Communications, 2012, 48(34): 4109. DOI:10.1039/c2cc30553d.
    [9] JIN X D(金晓东), WANG H(王浩), XIN R(辛然), et al. An aggregation-induced emission luminogen combined with a cyanoacrylate fuming method for latent fingerprint analysis[J]. The Analyst, 2020, 145(6): 2311-2318. DOI:10.1039/C9AN02158B.
    [10] JIN X D(金晓东), BI T(毕天博), XIN R(辛然), et al. Advances in the Application of Organic Materials for the Development of Latent Fingerprints[J]. Chinese Journal of Organic Chemistry (有机化学), 2020, 40(12): 4184. DOI:10.6023/cjoc202004036.
    [11] WANG K(王珂), YANG R Q(杨瑞琴), XIA B B(夏彬彬), et al. Water-Soluble fluorescent ZnxCd1-xSe quantum dots : synthesis and application for bloody fingerprint development materials reports[J], Materials Reports (材料导报),2010,24(24).
    [12] CHEN Y, LI A, LI X, et al. Multi‐Stimuli‐Responsive Amphiphilic Pyridinium Salt and Its Application in the Visualization of Level 3 Details in Latent Fingerprints[J]. Advanced Materials, 2023, 35(20): 2211917. DOI:10.1002/adma.202211917.
    [13] WANG Y L, LI C, QU H Q, et al. Real-Time Fluorescence In Situ Visualization of Latent Fingerprints Exceeding Level 3 Details Based on Aggregation-Induced Emission[J]. Journal of the American Chemical Society, 2020, 142(16): 7497-7505. DOI:10.1021/jacs.0c00124.
    [14] LIU M, CAO J, HUANG C, et al. A novel near-infrared fluorescent probe based on triphenylamine derivatives for the rapid and sensitive detection of heparin[J]. The Analyst, 2022, 147(15): 3504-3513. DOI:10.1039/D2AN00254J.
    [15] LIU W, WANG Y, WANG T, et al. A versatile AIE probe with mitochondria targeting for dual-channel detection of superoxide anion and viscosity[J]. Analytica Chimica Acta, 2023, 1253: 341099. DOI:10.1016/j.aca.2023.341099.
    [16] CAO Y, CHEN Y, SUN X, et al. Water sorption in ionic liquids: kinetics, mechanisms and hydrophilicity[J]. Physical Chemistry Chemical Physics, 2012, 14: 12252. DOI:10.1039/C2CP41798G.
    [17] ZHANG Y, WANG S, WANG X, et al. Monitoring of the decreased mitochondrial viscosity during heat stroke with a mitochondrial AIE probe[J]. Analytical and Bioanalytical Chemistry, 2021, 413(14): 3823-3831. DOI:10.1007/s00216-021-03335-2.
    [18] LU T, CHEN F. Multiwfn: A multifunctional wavefunction analyzer[J]. Journal of Computational Chemistry, 2012, 33(5): 580-592. DOI:10.1002/jcc.22885.
    [19] HUMPHREY W, DALKE A, SCHULTEN K. VMD: Visual molecular dynamics[J]. Journal of Molecular Graphics, 1996, 14(1): 33-38. DOI:10.1016/0263-7855(96)00018-5.
    [20] SONG Y, HU L, CHENG Q, et al. Benzothiazole derivatives with varied π-conjugation: synthesis, tunable solid-state emission, and application in single-component LEDs[J]. Journal of Materials Chemistry C, 2022, 10(16): 6392-6401. DOI:10.1039/D2TC00440B.
    [21] ZHU S, WANG H, HE Y, et al. Two polymorphs of a tetraphenylethene-substituted aza-borondiquinomethene complex and their emissions in different molecular packings[J]. Dyes and Pigments, 2022, 200: 110168. DOI:10.1016/j.dyepig.2022.110168.
    [22] CHEN W, WANG Y, NIU L N, et al. Crystal packing and mechanofluorochrmism of distyrylanthracene derivatives modulated by hydrogen bonds[J]. Journal of Luminescence, 2023, 257: 119680. DOI:10.1016/j.jlumin.2023.119680.
    [23] ETABTI H, FITRI A, BENJELLOUN A T, et al. Designing and theoretical study of benzocarbazole-based D-π-D type small molecules donor for organic solar cells[J]. Journal of Molecular Graphics and Modelling, 2023, 121: 108455. DOI:10.1016/j.jmgm.2023.108455.
    [24] HOU Y, LI Y, ZHANG M Y, et al. A dihedral-angle-controlled mechanochromic luminescent material: Application for pressure sensing[J]. Dyes and Pigments, 2020, 180: 108505. DOI:10.1016/j.dyepig.2020.108505.
    [25] SONG Z M(宋忠明), LIU R(刘睿), LI X(李希), et al. Tunable-emission and AIPE-active heteroleptic Ir(III) complexes for fingermark detection via a spraying technique[J]. Journal of Materials Chemistry C, 2018, 6(40): 10910-10915. DOI:10.1039/C8TC03984D.
    [26] DI L, XING Y, YANG Z, et al. Ultrabright AIE of Ir(III) complexes achieving expeditious monitoring of oxygen and high-definition development of latent fingerprints[J]. Sensors and Actuators B: Chemical, 2022, 350: 130894. DOI:10.1016/j.snb.2021.130894.
    引证文献
    网友评论
    网友评论
    分享到微博
    发 布
引用本文

蒋钊,孔兆宇,乔瑞洁,刘子川,宋林洲,朱森强,朱红军,刘睿.双亲性噻吩羧酸衍生物的制备及潜指纹检测应用[J].精细化工,2024,41(9):

复制
分享
文章指标
  • 点击次数:36
  • 下载次数: 1259
  • HTML阅读次数: 12
  • 引用次数: 0
历史
  • 收稿日期:2023-10-03
  • 最后修改日期:2023-12-18
  • 录用日期:2023-11-14
  • 在线发布日期: 2024-09-10
文章二维码