有机化学 ›› 2015, Vol. 35 ›› Issue (11): 2383-2388.DOI: 10.6023/cjoc201506021 上一篇    下一篇

研究简报

一种二茂铁与联萘酚修饰环三唑的合成及其对Zn2+双信号识别

王智成a, 戴博娜a, 丘继芳b, 曹迁永a, 葛金柱a   

  1. a 南昌大学化学系 南昌 330031;
    b 福建长汀第二中学 长汀 336300
  • 收稿日期:2015-06-17 修回日期:2015-07-09 发布日期:2015-08-17
  • 通讯作者: 曹迁永 E-mail:cqyong@ncu.edu.cn
  • 基金资助:

    国家自然科学基金(Nos. 21162017, 21462027)资助项目.

A New Ferrocene and Binaphthol Functionalized Triazolephane for Dual-Signaling Sensing of Zn2+

Wang Zhichenga, Dai Bonaa, Qiu Jifangb, Cao Qianyonga, Ge Jingzhua   

  1. a Department of Chemistry, Nanchang University, Nanchang 330031;
    b Fujian Province Changting No. 2 Middle School, Changting 336300
  • Received:2015-06-17 Revised:2015-07-09 Published:2015-08-17
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21162017, 21462027).

通过Click反应合成了一个新的含联萘酚荧光团与二茂铁电化学信号基团的环三唑化合物1. 在各种金属离子中, 化合物1对Zn2+有着很好的荧光及电化学信号响应. 随着Zn2+的加入, 化合物1位于380 nm发射峰增强并红移到428 nm, 同时其电位从430 mV正移到480 mV. 荧光滴定, 核磁氢谱滴定和密度泛涵理论(DFT)计算结果表明, 化合物1中三唑环中两个N原子和醚键上的O原子参与配位,同Zn2+形成稳定的1:1配合物.

关键词: 二茂铁, 环三唑, 荧光, 电化学, 金属离子识别

A new triazolephan-based receptor 1 bearing binaphthol fluorophore and ferrocene electrochemical singling site has been synthesized by “click reaction”. Among various metal ions, 1 shows exclusive multiple singles sensing of Zn2+ in CH3CN solution. Upon the addition of Zn2+, the fluorescence of 1 exhibited a red shift from 380 nm to 428 nm with enhancement the emission intensity. In addition, the Fe(III)/Fe(II) reversible redox potential of 1 was shifted from 430 mV to 480 mV. Fluorescence titration, 1H NMR titrations and DFT (density functional theory) calculation results reveal that the N atoms of triazole and O atoms of the ether groups take part in binding in 1-Zn2+ complexation with forming 1:1 complex.

Key words: ferrocene, triazolephane, fluorescence, electrochemistry, metal ions recognition