三足罗丹明B酰肼席夫碱化合物对Hg~(2+)的识别性质研究
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摘要
设计、合成并表征了1种新型的三足罗丹明B酰肼席夫碱化合物1.通过紫外-可见分光光度滴定和荧光滴定研究了阳离子和化合物1的相互作用.结果表明在16种金属离子中,只有Hg~(2+)对化合物1的荧光发射强度有显著的影响,化合物1对Hg~(2+)表现出高选择性和高灵敏度的发光和显色传感.体系的荧光随着汞离子的加入而增强,溶液颜色由无色变成粉红色.化合物1在乙醇-DMF (V/V=4∶1)溶液中与Hg~(2+)以1∶3的比例结合,结合常数为1. 66×106,最低检测限为3×10~(-7)mol/L.
A novel tripodal rhodamine B derivative compound 1 is synthesized and characterized. The interactions between the cations and this compound are studied through the titrimetry with UV-vis spectrophotometry and fluorescence spectra. The fluorescence investigations show that among the 16 metal ions only the fluorescence of compound 1 is remarkably affected upon the addition of Hg~(2+) . It can serve as a fluorescent and colorimetric sensor with high selectivity and sensitivity toward Hg~(2+) . The fluorescence intensity of compound 1 increases dramatically with the increasing concentration of Hg~(2+) ion,and the color of the solution changes from colorless to pink. Compound 1 exhibits a 1∶ 3 binding ratio with Hg~(2+) in Et OH/DMF solution( V/V = 4∶ 1) with the binding constant of 1. 66 × 106 and detection limit of 3 × 10~(-7) mol/L.
A novel tripodal rhodamine B derivative compound 1 is synthesized and characterized. The interactions between the cations and this compound are studied through the titrimetry with UV-vis spectrophotometry and fluorescence spectra. The fluorescence investigations show that among the 16 metal ions only the fluorescence of compound 1 is remarkably affected upon the addition of Hg~(2+) . It can serve as a fluorescent and colorimetric sensor with high selectivity and sensitivity toward Hg~(2+) . The fluorescence intensity of compound 1 increases dramatically with the increasing concentration of Hg~(2+) ion,and the color of the solution changes from colorless to pink. Compound 1 exhibits a 1∶ 3 binding ratio with Hg~(2+) in Et OH/DMF solution( V/V = 4∶ 1) with the binding constant of 1. 66 × 106 and detection limit of 3 × 10~(-7) mol/L.
引文
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[32]曾金凤,倪明,施冬健,等.罗丹明类衍生物基重金属离子荧光探针的研究[J].化学世界,2017,7:426-432.
[33] YANG H,ZHOU Z,HUANG K,et al. Multisignaling optical-electrochemical sensor for Hg2+based on a rhodamine derivative with a ferrocene unit[J]. Organic Letters,2007,9(23):4729-4732.
[34] SHIRAISHI Y,SUMIYA S,KOHNO Y,et al. A rhodamine-cyclen conjugate as a highly sensitive and selective fluorescent chemosensor for Hg(Ⅱ)[J]. Journal of Organic Chemistry,2008,73(21):8571.
[35] DUJOLS V,FORD A F,AWC. A long-wavelength fluorescent chemodosimeter selective for Cu(Ⅱ)ion in water[J]. Journal of the American Chemical Society,1997,119(31):7386-7387.
[36] FOURMIGU E'M,JOHANNSEN L,BOUBEKEUR K,et al. Tetrathiafulvalene-and dithiafulvene-substituted mesitylenes,new. pi.-donor molecules with 3-fold symmetry and the formation of an unprecedented new class of electroactive polymers[J]. Journal of the American Chemical Society,1993,24(36):3752-3759.
[37]许金钩,王尊本.荧光分析法[M].北京:科学出版社,2006.
[2] WEI T B,GAO G Y,QU W J,et al. Selective fluorescent sensor for mercury(II)ion based on an easy to prepare double naphthalene Schiff base[J]. Sensors&Actuators B Chemical,2014,199(4):142-147.
[3]陈红海,陈玉哲,李仲谨,等.反应型化学传感器的研究进展[J].有机化学,2012,32(1):46-56.
[4] KAGIT R,YILDIRIM M,OZAY O,et al. Phosphazene based multicentered naked-eye fluorescent sensor with high selectivity for Fe3+ions[J]. Inorganic Chemistry,2014,53(4):2144-2151.
[5]汪铭,张关心,张德清.基于聚集诱导荧光性质的免标记DNA四链体检测以及凝血酶的传感研究[J].影像科学与光化学,2015,33(1):77-83.
[6] WOZ'NICA E,MAKSYMIUK K,MICHALSKA A. Polyacrylate microspheres for tunable fluorimetric zinc ions sensor[J]. Analytical Chemistry,2014,86(1):411-418.
[7] BHALLA V,ROOPA,KUMAR M,et al. New fluorogenic sensors for Hg2+ions:through-bond energy transfer from pentaquinone to rhodamine[J]. Inorganic Chemistry,2012,51(4):2150-2156.
[8] RENZONI A,ZINO F,FRANCHI E. Mercury levels along the food chain and risk for exposed populations[J]. Environmental Research,1998,77(2):68.
[9] BOENING D W. Ecological effects,transport,and fate of mercury:a general review[J]. Chemosphere,2000,40(12):1335-1351.
[10] HOLLOWAY J M,DAHLGREN R A,HANSEN B,et al. Contribution of bedrock nitrogen to high nitrate concentrations in stream water[J]. Nature,1998,395(395):785-788.
[11] CZARNIK A W. Fluorescent Chemosensors of Ion and Molecule recognition[J]. Instrumentation Science&Technology,1993,22(4):405-406.
[12] CRAM D J. The Design of molecular hosts,guests,and their complexes[J]. Science,1988,6(4):397-413.
[13] DESVERGNE J P,CZARNIK A W. Chemosensors of ion and molecule recognition[M]. Springer Netherlands,1992.
[14] JANA A,KIM J S,JUNG H S,et al. A cryptand based chemodosimetric probe for naked-eye detection of mercury(II)ion in aqueous medium and its application in live cell imaging[J]. Chemical Communications,2009,29(29):4417-4419.
[15] ZHANG X,XIAO Y,QIAN X. A ratiometric fluorescent probe based on FRET for imaging Hg2+ions in living cells[J]. Angewandte Chemie,2008,47(42):8025-8029.
[16] SURESH M,MISHRA S,MISHRA S K,et al. Resonance energy transfer approach and a new ratiometric probe for Hg2+in aqueous media and living organism[J]. Organic Letters,2009,11(13):2740-2743.
[17] LIU W,XU L,ZHANG H,et al. Dithiolane linked thiorhodamine dimer for Hg2+recognition in living cells[J]. Organic&Biomolecular Chemistry,2009,7(4):660-664.
[18] CHEN X,NAM S W,JOU M J,et al. Hg2+selective fluorescent and colorimetric sensor:its crystal structure and application to bioimaging[J]. Organic Letters,2008,10(22):5235-5238.
[19] BISWAL B,BAG B. Preferences of rhodamine coupled(aminoalkyl)-piperazine probes towards Hg(Ⅱ)ion and their FRET mediated signaling[J]. Organic&Biomolecular Chemistry,2013,11(30):4975-4992.
[20]唐雪松,徐立谦,宋阳,等.一种对Hg2+进行裸眼识别和检测的新型若丹明类荧光探针[J].化学通报,2014,78(3):259-263.
[21]陈家逸,苏伟,王举恩.基于1,8-萘酰亚胺与罗丹明B间荧光共振能量转移的高选择性Hg2+比率荧光探针[J].高等学校化学学报,2016,2:232-238.
[22]焦扬,郑舒丹,周硼.水溶性荧光探针的制备、固载及对水中汞离子的识别[J].发光学报,2016,3:379-385.
[23] KIM H N,NAM S W,SWAMY K M,et al. Rhodamine hydrazone derivatives as Hg2+selective fluorescent and colorimetric chemosensors and their applications to bioimaging and microfluidic system[J]. Analyst,2011,136(7):1339-1343.
[24] DU J,FAN J,PENG X,et al. A new fluorescent chemodosimeter for Hg2+:selectivity,sensitivity,and resistance to Cys and GSH[J]. Organic Letters,2010,12(3):476-479.
[25] HUANG W,ZHOU P,YAN W,et al. A bright water-compatible sugar-rhodamine fluorescence sensor for selective detection of Hg2+in natural water and living cells[J]. Journal of Environmental Monitoring,2009,11(2):330-335.
[26] TANG L,LI F,LIU M,et al. Single sensor for two metal ions:colorimetric recognition of Cu2+and fluorescent recognition of Hg2+[J]. Spectrochimica Acta Part A Molecular&Biomolecular Spectroscopy,2011,78(3):1168-1172.
[27] KWON S K,KIM H N,RHO J H,et al. Rhodamine derivative bearing histidine binding site as a fluorescent chemosensor for Hg2+[J]. Cheminform,2009,40(31):719-721.
[28] KIM S K,SWAMY K M K,CHUNG S Y,et al. New fluorescent and colorimetric chemosensors based on the rhodamine and boronic acid groups for the detection of Hg2+[J]. Tetrahedron Letters,2010,51(25):3286-3289.
[29] YANG X F,LI Y,BAI Q. A highly selective and sensitive fluorescein-based chemodosimeter for Hg2+ions in aqueous media[J]. Analytica Chimica Acta,2007,584(1):95-100.
[30]孙京府,钱鹰.一种萘酰亚胺-罗丹明衍生物的合成、聚集诱导荧光增强及其双通道荧光探针性能[J].有机化学,2016,1:151-157.
[31]袁石状,张征宇,王举恩.基于萘酰亚胺的Hg2+和Cu2+荧光探针[J].化学研究与应用,2018,3:339-343.
[32]曾金凤,倪明,施冬健,等.罗丹明类衍生物基重金属离子荧光探针的研究[J].化学世界,2017,7:426-432.
[33] YANG H,ZHOU Z,HUANG K,et al. Multisignaling optical-electrochemical sensor for Hg2+based on a rhodamine derivative with a ferrocene unit[J]. Organic Letters,2007,9(23):4729-4732.
[34] SHIRAISHI Y,SUMIYA S,KOHNO Y,et al. A rhodamine-cyclen conjugate as a highly sensitive and selective fluorescent chemosensor for Hg(Ⅱ)[J]. Journal of Organic Chemistry,2008,73(21):8571.
[35] DUJOLS V,FORD A F,AWC. A long-wavelength fluorescent chemodosimeter selective for Cu(Ⅱ)ion in water[J]. Journal of the American Chemical Society,1997,119(31):7386-7387.
[36] FOURMIGU E'M,JOHANNSEN L,BOUBEKEUR K,et al. Tetrathiafulvalene-and dithiafulvene-substituted mesitylenes,new. pi.-donor molecules with 3-fold symmetry and the formation of an unprecedented new class of electroactive polymers[J]. Journal of the American Chemical Society,1993,24(36):3752-3759.
[37]许金钩,王尊本.荧光分析法[M].北京:科学出版社,2006.