有机化学 ›› 2017, Vol. 37 ›› Issue (12): 3274-3281.DOI: 10.6023/cjoc201706037 上一篇    下一篇

研究简报

一种具有聚集诱导发光性质的Fe3+荧光探针的合成及性能研究

刘瑞姣, 曾竟   

  1. 新疆师范大学化学化工学院 乌鲁木齐 830054
  • 收稿日期:2017-06-28 修回日期:2017-08-08 出版日期:2017-12-25 发布日期:2017-09-15
  • 通讯作者: 曾竟, 刘瑞姣 E-mail:zengjing800111@163.com;lrjxjnu@163.com
  • 基金资助:

    新疆维吾尔自治区自然科学基金(No.2015211B024)和新疆师范大学博士启动基金(No.XJNUBS1508)资助项目.

Study on a Novel Colorimetric and Off-On Fluorescent Chemosensor with Aggregation-Induced Emission Effect for Detection of Fe3+ in Aqueous Solution

Liu Ruijiao, Zeng Jing   

  1. College of Chemistry and Chemical Engineering, Xinjiang Normal University, Urumqi 830054
  • Received:2017-06-28 Revised:2017-08-08 Online:2017-12-25 Published:2017-09-15
  • Contact: 10.6023/cjoc201706037 E-mail:zengjing800111@163.com;lrjxjnu@163.com
  • Supported by:

    Project supported by the Natural Science Foundation of Xinjiang Uygur Aotonomous Region (No. 2015211B024) and the Doctoral Scientific Research Foundation of Xinjiang Normal University (No. XJNUBS1508).

通过乙二醛将1,1-二(4-甲基苯基)-2-(4-氨基苯基)-2-苯基乙烯和罗丹明B酰肼连接起来,合成了一种四苯乙烯官能团化的罗丹明B衍生物TPE-RhB.利用IR,NMR,MS和元素分析等对其进行了表征,确定了分子结构.并通过循环伏安分析法、紫外-可见光谱法、分子荧光光谱法等分别考察了它的电化学和光学性质.研究表明TPE-RhB的电子亲合能为3.66 eV,有望开发为电子传输材料.此化合物在纯乙醇溶液中,几乎没有荧光,在乙醇/水的混合溶剂中具有典型聚集诱导发光(AIE)性能.更为重要的是在乙醇/水(VV=1:1,Tris-HCl pH 7.0)混合溶液中能对Fe3+实现"off-on"荧光识别,并裸眼可观察到溶液颜色从淡黄色变成粉红色,且几乎不受其他共存离子的干扰.探针与Fe3+的结合常数为3.12×103,检出限可达3.53×10-7 mol·L-1,Fe3+离子含量范围在6×10-5~1.8×10-4 mol·L-1时,荧光强度与Fe3+离子浓度呈良好的线性关系(R2=0.9915),并通过Job's曲线、紫外和荧光滴定、核磁滴定初步确定了化合物TPE-RhB和Fe3+的络合机理.

关键词: 四苯乙烯, 罗丹明B, 聚集诱导荧光, 荧光探针, 光电材料

A novel tetraphenylethyene-functionalized rhodamine derivative (TPE-RhB) was designed and synthesized. FT-IR, NMR, MS, elemental analysis, cyclic voltammetry electrochemical analysis, UV-Vis, and molecular fluorescence were used to study its structure, electrochemical and optical properties. These results showed that the electron affinity of TPE-RhB was 3.66 eV, which is expected to develop electron-transporting material. A significant aggregation-induced emission (AIE) effect of TPE-RhB was found through solution fluorescence test in different V(EtOH):V(H2O) mixed solvents. Furthermore, sensor TPE-RhB displayed highly seletive and sensitive off-on fluorescence response and naked-eye color change to Fe3+ in EtOH/H2O (V:V=1:1, Tris-HCl pH 7.0) solution. The association constant between TPE-RhB and Fe3+ was detected to be 3.12×103 and the detection limit was calculated to be 3.53×10-7 mol·L-1. The probe TPE-RhB also showed a good linearity (R2=0.9915) in the range of 60~180 μmol/L of Fe3+ ion. The mechanisms had been supported by Job's plot evalution, fluorescence titrations, and 1H NMR spectroscopic studies.

Key words: tetraphenylethyene, rhodamine B, aggregation-induced emission (AIE) effect, fluorescent chemosensor, optoelectronic material