合成了新型苯并噻唑类的螺吡喃化合物3-苄基-8′-甲氧基-6′-硝基-3H-螺[苯并[d]噻唑-2,2′-苯并吡喃]即SP,其可以作为比色和荧光化学传感器,用来检测溶液中的三价金属离子铁、铬和铝。由于苯并噻唑类螺吡喃化合物特殊的结构与性能,在不同的光照条件下此化合物SP可以作为重要的光响应分子。采用紫外-可见分光光度计、荧光-分光光度计、傅里叶红外光谱仪和核磁共振仪分析了化合物的性能。结果表明:此化合物具有良好的裸眼识别效果、紫外和荧光识别效果,良好的抗干扰性,较快的响应时间和较低的检测限等优点。
Novel benzothiazole spiropyran compound,3-benzyl-8′-methoxy-6′-nitro-3H-spiro[benzo[d]thiazole-2,2′-benzopyran],was synthesized as colorimetric and fluorescent chemical sensors for the detection of Fe3+,Cr3+ and Al3+.Due to the special structure and properties of the benzothiazole spiropyran compound,they can be used as important photo-responsive molecules under different light conditions.The properties of the compound was analyzed using UV-Vis spectrophotometer,Fluorescence spectrophotometer,fourier infrared spectroscopy,and nuclear magnetic resonance instrument.It had the advantages of good naked-eye recognition,UV and fluorescence recognition,good anti-interference,faster response time,and lower detection limit.
[1] Pisignano D,Mele E,Persano L,et al.Optical gain from the open form of a photochromic molecule in the solid state[J].Journal of Physical Chemistry B,2006,110:4506-4509.
[2] Xia H Y,Xu Y Y,Yang G,et al.A reversible multi-stimuli-responsive fluorescence probe and the design for combinational logic gate operations[J].Macromolecular Rapid Communications,2014,35:303-308.
[3] Gumbley P,Thomas S W.Reversible photochemical tuning of net charge separation from contact electrification[J].ACS Applied Materials ＆ Interfaces,2014,6:8754-8761.
[4] Inouye M,Ueno M,Kitao T.Alkali metal recognition induced isomerization of spiropyrans[J].Journal of the American Chemical Society,1990,112:8977-8979.
[5] 孙宾宾,傅正生,陈洁.光致变色材料在军事领域的应用[J].陕西国防工业职业技术学院学报,2007,17(1):38-40.
[6] Berkovic G,Krongauz V,Weiss V.Spiropyrans and spirooxazines for memories and switches[J].Chemical Reviews,2000,100:1741-1753.
[7] Pisignano D,Mele E,Persano L,et al.Optical gain from the open form of a photochromic molecule in the solid state[J].Journal of Physical Chemistry B,2006,110:4506-4509.
[8] Meng J X,Xu H N,Li Z Y,et al.A turn-on spiropyran derivative based reversible photo-driven colorimetric and fluorescent chemosensor for trivalent metal ions[J].Tetrahedron,2017,73:6637-6643.
[9] Rahman F U,Ali A,Khalild S K,Tuning sensitivity of a simple hydrazone for selective fluorescent “turn on” chemo-sensing of Al3+ and its application in living cells imaging[J].Talana,2017,164:307-313.
[10] Wang Q M,Sun H F,Jin L,et al.A novel turn on and reversible sensor for Al3+ and its applications in bioimaging[J].Journal of Luminescence,2018,203:113-120.
[11] 王希峰,田进涛.含羟基螺吡喃化合物的合成及其光谱性能研究[J].科技视界,2015(22):9-10.
[12] Wang B,Chen K F,Yang R D,et al.Photoresponsive nanogels synthesized using spiropyrane-modified pullulan as potential drug carriers[J].Journal of Applied Polymer Science,2014,131:40288-40296.
[13] Morgunov R B,Mushenok F B,Aldoshin S M,et al.Thermally-induced paramagnetism of spiropyrane iodides[J].New Journal of Chemistry,2009,33:1374-1379.
[14] Chen X B,Qi C X,Li H,et al.Highly sensitive and selective Fe3+ detection by a water-stable Tb3+-doped nickel coordination polymer-based turn-off fluorescence sensor[J].Journal of Solid State Chemistry,2020,281:121030-121038.
[15] SağAırlı A,Bozkurt E.Rhodamine-based arylpropenone azo dyes as dual chemosensor for Cu2+/Fe3+ detection[J].Journal of Photochemistry and Photobiology A:Chemistry,2020,403:112836-112848.
[16] Cao X,Zhang F,Bai Y,et al.A highly selective “turn-on” fluorescent probe for detection of Fe3+ in cells[J].J Fluoresc,2019,29:425-434.
[17] 张莹莹,黄译文,赵冰.Cr3+比色荧光探针的合成及细胞成像应用[J].高等学校化学学报,2019,40(12):2486-2493.
[18] Ezhumalai D,Mathivanan L,Chinnadurai A.A novel dual chemosensor for selective heavy metal ions Al3+,Cr3+ and its applicable cytotoxic activity,HepG2 living cell images and theoretical studies[J].Journal of Molecular Structure,2020,1210:128033.
[19] Cheah P W,Heng M P,Izati A,et al.Rhodamine B conjugate for rapid colorimetric and fluorimetric detection of aluminium and tin ions and its application in aqueous media[J].Inorganica Chimica Acta,2020,512:119901-119909.
[20] Kaur N,Kaur B.Colorimetric and fluorescent multi-ion recognition by anthracene appended di-Schiff base chemosensor[J].Inorganic Chemistry Communications,2020,121:108239-108241.
[21] Wang Y,Xu Z,Dai X,et al.A new spiropyran-based sensor for colorimetric and fluorescent detection of divalent Cu2+ and Hg2+ ions and trivalent Ce3+,Cr3+ and Al3+ ions[J].J Fluoresc,2019,29(3):569-575.
[22] Zhang R,Hu L,Xu Z,et al.A highly selective probe for fluorescence turn-on detection of Fe3+ ion based on a novel spiropyran derivative[J].Journal of Molecular Structure,2020,1204:127481-127489.
[23] Yildiz L,Deniz E,Raymo F M.Fluorescence modulation with photochromic switches in nanostructured constructs[J].Chemical Society Reviews,2009,38:1859-1867.
[24] Tian Z,Wu W,Wan W,et al.Single-chromophore-based photoswitchable nanoparticles enable dual-alternating-color fluorescence for unambiguous live cell imaging[J].Journal of the American Chemical Society,2009,131:4245-4252.
[25] Gorner H,Atabekyan L S,Chibisov A K.Photoprocesses in spiropyran-derived merocyanines:singlet versus triplet pathway[J].Chemical Physics Letters,1996,260:59-64.
