Synthesis of Crown Ether Metal-prophyrin and Its Anion Recognition

doi:10.11944/j.issn.1000-0518.2015.02.140140

Chinese Journal of Applied Chemistry ›› 2015, Vol. 32 ›› Issue (2): 171-176.DOI: 10.11944/j.issn.1000-0518.2015.02.140140

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Synthesis of Crown Ether Metal-prophyrin and Its Anion Recognition

GENG Xin^a, CHEN Cai^a, LI Guocheng^a, GAO Kangli^a, DENG Zhaojing^a, HAN Guozhi^b

aCollege of Science,Nanjing University of Technology,Nanjing 210009,China
bState Key Laboratory of Molecular Electronics,Southeast University,Nanjing 210096,China

Received:2014-04-21 Revised:2014-07-09 Published:2015-02-10 Online:2015-02-10
Contact: Corresponding author:HAN Guozhi, associate professor; Tel/Fax:025-83587428; E-mail:han@njtech.edu.cn; Research interests:function materials chemistry
Supported by:
Supported by Open Project of State Key Laboratory of Molecular Electronics, Southeast University（No.20111218）

Abstract

Abstract:

A benzo-15-crown-5 modified 5-(4-carboxyphenyl)-10,15,20-triphenylporphyrin(1) was synthesized and used for binding with Hg²⁺ ion to form crown ether metal-prophyrin complex(3). UV-Vis and ¹H NMR were used to investigate the formation and self-assembly of complex 3. The difference of ¹H NMR spectra of complexes 3 and 2 reveals that a synergy effect of prophyrin and crown ether exists. The anion recognition and mechanism of complex 3 were also studied. After addition of NaNH₂, an obvious red shift in the UV-Vis spectra was observed accompanied with a color change from green to chartreuse viewed by naked eye. At the same time, the chemical shift of —CH₂— in crown ether ring shifted from 3.12 to 3.16 and 3.32 to 3.34, respectively. This phenomenon can be explained by the strong nucleophilic property of amino anion. However, addition of other sodium salts such as NaCl, NaH₂PO₄ and NaHCO₃ could not result in the same phenomenon. This study provides a method for visible anion recognition.

Key words: crown ether, porphyrin, synthesis, anion, visible recognition

CLC Number:

O621.2

GENG Xin, CHEN Cai, LI Guocheng, GAO Kangli, DENG Zhaojing, HAN Guozhi. Synthesis of Crown Ether Metal-prophyrin and Its Anion Recognition[J]. Chinese Journal of Applied Chemistry, 2015, 32(2): 171-176.

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Synthesis of Crown Ether Metal-prophyrin and Its Anion Recognition

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