罗丹明B类衍生物的合成及其对Cu~(2+)的识别研究
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摘要
以罗丹明B,水合肼和5-甲基水杨醛为原料,合成了5-甲基水杨醛-罗丹明类衍生物探针L。用经红外、核磁和质谱对其分子结构进行了表征,并采用紫外光谱法研究了其对Cu~(2+)的识别特性。结果表明:探针L对Cu~(2+)有选择性比色识别,在Cu~(2+)浓度1.0～10.0μmol·L~(-1)范围内,探针L在562nm处的吸光度与Cu~(2+)浓度呈现良好的线性关系(R=0.9994),检出痕为0.26μmol·L~(-1);Job曲线表明,探针与Cu~(2+)的络合比为1:1;利用探针L对Cu~(2+)的可逆性实验探索了探针的响应机理。
The 5-methylsalicylaldehyde-rhodamine-based probe L was synthesized from rhodamine B,hydrazine hydrate and 5-methylsalicylaldehyde.The structure of product was characterized by ~1H NMR,IR and MS.The recognition properties of the probe for Cu~(2+) had been investigated by the ultraviolet spectroscopy.The results showed that the probe L displayed high selective colorimetric recognition of Cu~(2+) and a good linear relationship between the absorbance of probe L at 562 nm with concentration of Cu~(2+)from 1.0 to 10.0μmol·L~(-1 )(R=0.9994),and the detection limit is 0.26μmol·L~(-1).The method of Job's confirmed the 1:1 complex between Cu~(2+) and probe L.The recognition mechanism of probe was explored by using the probe L in the reversibility experiment of Cu~(2+).
The 5-methylsalicylaldehyde-rhodamine-based probe L was synthesized from rhodamine B,hydrazine hydrate and 5-methylsalicylaldehyde.The structure of product was characterized by ~1H NMR,IR and MS.The recognition properties of the probe for Cu~(2+) had been investigated by the ultraviolet spectroscopy.The results showed that the probe L displayed high selective colorimetric recognition of Cu~(2+) and a good linear relationship between the absorbance of probe L at 562 nm with concentration of Cu~(2+)from 1.0 to 10.0μmol·L~(-1 )(R=0.9994),and the detection limit is 0.26μmol·L~(-1).The method of Job's confirmed the 1:1 complex between Cu~(2+) and probe L.The recognition mechanism of probe was explored by using the probe L in the reversibility experiment of Cu~(2+).
引文
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[2]翟荣佳,刘娅静,赵鑫,等.一种罗丹明类Cu2+荧光探针化合物的合成及性能研究[J].化学研究与应用,2015,27(9):1278-1282.
[3]冯媛娇,杨晓明,朱姗姗,等.基于L-半胱氨酸合成的金纳米簇用于铜离子和多西环素的检测[J].中国科学:化学,2015,45(1):90-97.
[4]王芹,汪怡,王露,等.磁性固相萃取-火焰原子吸收光谱法测定工业废水中的Cu2+[J].理化检验:化学分册,2016,52:15-18.
[5]Tang L J,Zhao G Y,Wang N N.Fluorescent“off-on”recognition of copper(Ⅱ)ions by a simple carbazole-based probe[J].Chemical Research and Application,2013,25(7):946-950.
[6]Dong Eun Kang,Chang Su Lim,Ji Yeon Kim,et al.Two-photon probe for Cu2+ with an internal reference:Quantitative estimation of Cu2+ in human tissues by two-photon microscopy[J].Anal Chem,2014,86:5353-5359.
[7]冯鹏青,焦晨旭,郭凌雁,等.石墨烯修饰碳糊电极循环伏安法测定铜离子[J].材料科学与工程学报,2014,32(4):554-448
[8]刘赵荣,弓巧娟,王玉春,等.电聚合β-环糊精修饰电极的制备及其对铜离子的检测[J].分析科学学报,2012,28(4):543-546.
[9]左航,陈艺贞,陈建华,等.ICP-MS研究黄河三湖河口表层沉积物对Cd2+和Cu2+的吸附-解吸特性[J].光谱学与光谱分析,2017,37(3):902-909
[10]Dong Hee Joo,Jin Su Mok,Geon Hwan Bae,et al.Colorimetric Detection of Cu2+ and Fluorescent Detection of PO43- and S2- by a Multifunctional Chemosensor[J].Ind Eng Chem Res,2017,56:8399-8407.
[11]Yibing Shi,Roumin,Wei Yuan,et al.Easy-to-Use Colorimetric Cyanine Probe for the Detection of Cu2+ in Wilson's Disease[J].ACS Appl Mater Interfaces,2018,10:20377-20386.
[12]Balakrishnan Muthuraj,Rohitas Deshmukh,Vishal Trivedi,et al.Highly selective probe detects Cu2+ and endogenous NO gas in living cell[J].ACS Appl Mater Interfaces,2014,6,6562-6569.
[13]恩达,孙晓红,延永.香豆素-铜离子(Ⅱ)配合物硫醇荧光探针的合成及荧光性质[J].精细化工,2014,31(10):1183-1187.
[14]常昂,吴尚荣,柳影,等.基于新铜试剂的Cu2+荧光探针的合成及性能研究[J].分析科学学报,2016,32(1):58-62.
[15]周丽波,赵秋媛,李宜,等.基于高半胱氨酸-罗丹明类荧光探针的合成及其对不中铜离子的检测[J].分析试验室,2018,37(8):893-897.
[16]周高,冯锋,陈泽忠,等.一种新型荧光探针的合成及其对Cu2+的选择性识别[J].光谱学与光谱分析,2017,37(9):2799-2803.