Synthesis and properties of Fe3+ probe based on ring-opening and ring-closing
LI Changjiang1,2, LI Qing1, ZHANG Liyan3, ZHENG Yuchuan1,2, PAN Le1, KE Zhongcheng1, LI Bowen4*
1(School of Chemistry and Chemical Engineering, HuangShan University, Huangshan 245041, China) 2(Key Laboratory of Inorganic Functional Materials, HuangShan University, Huangshan 245041, China) 3(School of Chemistry and Chemical Engineering, Anhui University of Technology, Ma′anshan 243032, China) 4(College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China)
Abstract: Iron is an important trace element in the human body and plays an important role in human health. In this paper, a novel compound (named R1) has been synthesized by using rhodamine B, ethylenediamine and o-vanillin as raw materials. The structure of R1 was characterized by nuclear magnetic resonance and mass spectrum, and the properties just as ion selectivity, reaction complex ratio and sensitivity were tested. Results showed that R1 can selectively recognize Fe3+. As the color of the solution changed significantly, the fluorescence also changed. According to the calculation of job's plot curve, the complex ratio of R1 toward Fe3+ was 1∶1. Meanwhile, R1 for Fe3+ sensing had a remarkable low detection limit of 146 mmol/L (UV) and 129 mmol/L (fluorescence), which is far below the drinking water standards (0.3 mg/L) of China. Furthermore, the cellular imaging and cytotoxicity experiments demonstrated that R1 could be used for sensing Fe3+in vivo due to its low cytotoxicity and good biocompatibility. Therefore, as a new type of visual fluorescent probe, R1 could be effectively applied to the content detection of Fe3+ in the fields of food safety, environment, biology, etc.
李长江,李晴,张莉艳,等. 基于“开-闭”环的铁离子探针的合成及性能研究[J]. 食品与发酵工业, 2020, 46(13): 107-113.
LI Changjiang,LI Qing,ZHANG Liyan,et al. Synthesis and properties of Fe3+ probe based on ring-opening and ring-closing[J]. Food and Fermentation Industries, 2020, 46(13): 107-113.
[1] 汪学荣, 郑炯, 阚建全. 铁代谢及生理功能研究进展[J]. 粮食与油脂, 2008(11):47-49. [2] WANG Y, CHANG H Q, WU W N, et al. Rhodamine-2-thioxoquinazolin-4-one conjugate: a highly sensitive and selective chemosensor for Fe3+ ions and crystal structures of its Ag(I) and Hg(II) complexes[J]. Sensors & Actuators B Chemical, 2017, 239:60-68. [3] ZHANG G, LU B, WEN Y, et al. Facile fabrication of a cost-effective, water-soluble, and electrosynthesized poly(9-aminofluorene) fluorescent sensor for the selective and sensitive detection of Fe(III) and inorganic phosphates[J]. Sensors & Actuators B Chemical, 2012, 171-172(8):786-794. [4] SEMPOS C T, GILLUM R F, LOOKER A C. Iron and heart disease:The epidemiologic data[J]. Nutrition Reviews, 1996,54(3):73-84. [5] SWAMINATHAN S, FONSECA V A, ALAM M G, et al. The role of iron in diabetes and its complications[J]. Diabetes Care, 2007, 30(7):1 926-1 933. [6] ESCHBACH J W, ADAMSON J W. Iron overload in renal failure patients: Changes since the introduction of erythropoietin therapy[J]. Kidney International Supplement, 1999, 69(69):S35-S43. [7] 胡述容. 食品中铁测定法的研究[J]. 食品与发酵工业, 1988,14(5):34-40;21. [8] TIAN Z, LIU Y, TIAN B, et al. Synthesis and proton-induced fluorescence “OFF-ON” switching of a new D-π-A type pyran dye[J]. Research on Chemical Intermediates, 2015, 41(2):525-533. [9] 周静, 钱亮亮, 冯洪燕, 等. 电感耦合等离子体质谱法检测塑料饮用吸管中金属元素的迁移量[J]. 食品科学, 2018, 39(8):276-281. [10] 张虹艳, 丁武, 吴福祥,等. 自动石墨消解-电感耦合等离子体质谱法监测干制水产品中的铅、砷、铝、铬、铁、铜[J]. 食品与发酵工业, 2019, 45(3):266-269. [11] 徐鉴, 扶庆权, 张辉, 等. 8-羟基喹啉类荧光探针的合成及其对食品中Al3+含量的检测[J]. 食品科学, 2017, 38(18):292-296. [12] 程海星, 郭月英, 任霆, 等. 实时荧光定量PCR技术原理及在食品检测中的应用[J]. 食品与发酵工业, 2015, 41(3):243-247. [13] CHEN X, PRADHAN T, WANG F, et al. Fluorescent chemosensors based on spiroring-opening of xanthenes and related derivatives[J]. Chemical Reviews, 2012, 112(3):1 910-1 956. [14] 常晓曦, 王佳, 宋杨, 等. 纳米金-罗丹明B协同作用在食品安全快速检测中的研究概述[J]. 食品与发酵工业, 2019, 45(6):243-248. [15] LI C J, XIANG K Q, LIU Y C, et al. A novel colorimetric chemosensor for Cu2+ with high selectivity and sensitivity based on Rhodamine B[J]. Research on Chemical Intermediates, 2015, 41(12):10 169-10 180. [16] 闫晨, 周炎, 洪诚毅, 等. 基于碳量子点和罗丹明B的新型比率荧光试纸片检测水中Hg(Ⅱ)[J]. 光谱学与光谱分析, 2019, 39(11):3 426-3 432. [17] 杨俊卿, 吴芳辉, 罗祥瑞, 等. 对Zn2+及S2-连续响应的罗丹明B酰肼类荧光探针的研究[J]. 分析测试学报, 2019, 38(10):1 265-1 269. [18] 洪利明, 张志兰, 陈熙,等. 罗丹明B类衍生物的合成及其对Cu2+的识别研究[J]. 化学研究与应用, 2019, 31(3):522-526. [19] 刘静, 谈光华, 王欢, 等. 基于off-on机理的罗丹明Ag+荧光探针合成与识别性能[J]. 高校化学工程学报, 2018, 32(4):949-955. [20] 徐海燕, 刘媛. 构建碳点-罗丹明B比率探针检测汞离子污染[J]. 北京师范大学学报(自然科学版), 2019, 55(6):700-708. [21] 张玲菲, 赵江林, 曾晞, 等. 苯基乙酰丙酮-罗丹明B衍生物的合成及对Fe3+离子的识别性质研究[J]. 无机化学学报, 2010, 26(10):1 796-1 803. [22] 宋方方, 赵岗, 光善仪, 等. 一种新型罗丹明基衍生物分子的合成[J]. 合成化学, 2018, 26(11):833-835. [23] DAN W, DENG X K, YU Y H. A novel turn-on fluorescent probe for Hg2+ detection based on rhodamine B spirolactam derivative[J]. International Journal of Environmental Analytical Chemistry, 2019, 99(15):1 515-1 527. [24] CHEN H, JIN X, ZHANG W, et al. A new rhodamine B-based “off-on” colorimetric chemosensor for Pd2+, and its imaging in living cells[J]. Inorganica Chimica Acta, 2018, 482:122-129. [25] MECIT OZDEMIR, ZHANG Y, GUO M L. A highly selective “off-on” fluorescent sensor for subcellular visualization of labile iron(III) in living cells[J]. Inorganic Chemistry Communications, 2018, 90:73-77. [26] YU C W, JIAN L, JI Y X, et al. Al(Ⅲ)-responsive “off-on” chemosensor based on rhodamine derivative and its application in cell imaging[J]. RSC Advances, 2018, 8(54):31 106-31 112. [27] GB 5749—2006, 生活饮用水卫生标准[S]. 北京:中国标准出版社, 2007.
2020, Vol. 46 
