苯并噻唑类荧光探针N-BPA在苦味酸检测中的应用A New Benzothiazole Fluorescent Probe N-BPA Was Synthesized for the Detection of Picric Acid
张春侠,燕宇航,堵爱农,赵旭飞,陈太杰
摘要(Abstract):
文章以2-甲基苯并噻唑为母核,经硝化、催化氢化、Sonogashira偶联、Knoevenagel缩合等反应,以及烯炔双链接桥设计来合成了一种荧光探针N-BPA。光谱分析发现,该探针分子具有148 nm的较大Stokes位移,可以有效避免探针成像过程中的自猝灭现象,同时具有1.285×10~4L/mol的较高拟合结合常数,说明探针分子与苦味酸的结合程度随浓度增加明显增强,其检测限达到5.42×10~(-4) mol/L。此外,其他常见硝基化合物对探针分子无明显干扰,表明该苯并噻唑类荧光探针具有较好的苦味酸识别能力。
关键词(KeyWords): 荧光探针;苯并噻唑;苦味酸;Stokes位移
基金项目(Foundation): 安徽省高等学校自然科学研究重点项目(KJ2016A425)
作者(Author): 张春侠,燕宇航,堵爱农,赵旭飞,陈太杰
DOI: 10.13757/j.cnki.cn34-1328/n.2025.03.012
参考文献(References):
- [1]VINAYAGAM D, SUBRAMANIAN K. A phenothiazine-functionalized pyridine-based AIEE-active molecule:a versatile molecular probe for highly sensitive detection of hypochlorite and picric acid[J]. RSC Advances, 2024, 14(8):5149-5158.
- [2]WANG L, ZHAI L Y, LIANG Z Y, et al. Dual mode detection of picric acid with fluorescence and smartphone colorimetry via AIE active tetraphenylethylene derivatives[J]. Dyes and Pigments, 2023, 220:111743.
- [3]JYOTI K G, NASRIN S, NEELOTPAL S S. Duel phase selective inner filter effect-based luminescent sensing for the detection of para-nitrophenol and picric acid[J]. Sensors and Actuators B:Chemical, 2023, 374:132778.
- [4]HUSSAIN S, MALIK A H, AFROZ M A, et al. Ultrasensitive detection of nitroexplosive-picric acid via a conjugated polyelectrolyte in aqueous media and solid support[J]. Chemical Communications, 2015, 51(33):7207-7210.
- [5]SHANMUGARAGU S, JOSHI S A, MUKHERJEE P S. Fluorescence and visual sensing of nitroaromatic explosives using electron rich discrete fluorophores[J]. Journal of Materials Chemistry, 2011, 21(25):9130-9138.
- [6]赵永梅,穆叶舒,洪琛等.双萘酰亚胺衍生物用于检测水溶液中的苦味酸[J].高等学校化学学报, 2022, 43(3):47-55.
- [7]BANDELA A K, BANDAEU S, RAO C P. A Fluorescent 1,3-diaminonaphthalimide conjugate of calix[4]arene for sensitive and selective detection of trinitrophenol:spectroscopy, microscopy, and computational studies, and its applicability using cellulose strips[J]. Chemistry-A European Journal, 2015, 21(38):13364-13374.
- [8]SANCHEZ J C, TROGLER W C. Efficient blue-emitting silafluorene-fluorene-conjugated copolymers:selective turn-off/turn-on detection of explosives[J]. Journal of Materials Chemistry, 2008, 18(26):3143-3156.
- [9]TOAL S J, TROGLER W C. Polymer sensors for nitroaromatic explosives detection[J]. Journal of Materials Chemistry, 2006, 16(28):2871-2883.
- [10]SHANMUGARAJU S, MUKHERGEE P S. Self-assembled discrete molecules for sensing nitroaromatics[J]. Chemistry-A European Journal,2015, 21(18):6656-6666.
- [11]SHANMUGARAJU S, MUKHERJEE P S.π-electron rich small molecule sensors for the recognition of nitroaromatics[J]. Chemical Communications, 2015, 51(89):16014-16032.
- [12]ZHOU H, LI J S, CHUA M H, et al. Poly(acrylate)with a tetraphenylethene pendant with aggregation-induced emission(AIE)characteristics:highly stable AIE-active polymer nanoparticles for effective detection of nitro compounds[J]. Polymer Chemistry, 2014, 5(19):5628-5637.
- [13]BRETT J, THEODORB B, MARIA S, et al. Simple high-performance liquid chromatographic method to analyze serum creatinine has several advantages over the Jaffépicric acid reaction as demonstrated with a cimetidine dose response in rhesus monkeys[J]. Journal of Chromatography B:Biomedical Sciences and Applications, 2001, 759(2):343-348.
- [14]刘静云.苯并噻唑类化合物的合成及荧光性质研究[D].上海:东华大学, 2016.
- [15]冯瑞卿.基于苯并噻唑(咪唑)的膜通透性双光子生物荧光染料的设计、合成及其在细胞成像中的应用[D].济南:山东大学, 2017.
- [16]韩荞霞,单斌,刘雅宁,等.荧光探针在水中汞离子检测中的研究进展[J].山东化工, 2021, 50(15):63-66.
- [17]SANGSUWAN W, FAIKHRUEA K, SUPABOWORNSATHIT K, et al. Design, synthesis, and characterization of novel Styryl dyes as fluorescent probes for Tau aggregate detection in vitro and in cells[J]. Chemistry-An Asian Journal, 2024, 19(6):e202301081.
- [18]GAN M Y, YAO R, WANG B P, et al. 3-aminophenylboronic acid modified carbon nitride quantum dots as fluorescent probe for selective detection of dopamine and cell imaging[J]. Methods and Applications in Fluorescence, 2024, 12(2):137-139.
- [19]CUI J, ZANG S P, NIE H L, et al. An ICT-based fluorescent probe for ratiometric monitoring the fluctuations of peroxynitrite in mitochondria[J].Sensors and Actuators B:Chemical, 2021, 328:129069.
- [20]GUO Y T, PAN Y X, TANG L J. Progresses in reactive fluorescent probes with fused aggregation-induced emission(AIE)and excited state intramolecular proton transfer(ESIPT)structures[J]. Chinese Journal of Organic Chemistry, 2022, 42(6):1640-1650.
- [21]谭轶群.基于苯并噻唑和三联吡啶荧光探针的设计合成及功能研究[D].杭州:浙江大学, 2014.
- [22]任宏.基于苯并噻唑的比色荧光探针对CN-的识别检测[D].太原:山西大学, 2020.
- [23]CHEN Y M, ZHANG K, TAN J C, et al. Design, synthesis, and pharmacological evaluation of novel benzothiazole derivatives targeting LCK in acute lymphoblastic leukemia[J]. Bioorganic Chemistry, 2024, 144:107180.
- [24]SHANG J F, ZHANG Y, YANG N, et al. Synthesis and biological evaluation of novel pyridylpyrazole amides containing benzothiazole/thiourea/urea motif as pesticidal agents[J]. Phosphorus, Sulfur, and Silicon and the Related Elements, 2023, 198(8):659-672.
- [25]YANG F, WILKINSON M, AUSTIN E J, et al. Origin of the Stokes shift:a geometrical model of exciton spectra in 2D semiconductors[J].Physical Review Letters, 1993, 70(3):323-326.
- [26]REN T B, XU W, ZHANG W, et al. A general method to increase Stokes shift by introducing alternating vibronic structures[J]. Journal of the American Chemical Society, 2018, 140(24):7716-7722.
- [27]汪欢.具有大Stokes位移的水溶性荧光探针的合成及应用研究[D].西安:西北大学, 2018.