Fluorescence emission control and switching of oxymethylcrowned spirobenzopyrans by metal ion

被引：46

作者：

Ahmed, SA

Tanaka, M

Ando, H

Tawa, K

Kimura, K

机构：

[1] AIST, Special Div Human Life Technol, Ikeda, Osaka 5638577, Japan

[2] Wakayama Univ, Fac Syst Engn, Dept Appl Chem, Wakayama 6408510, Japan

来源：

TETRAHEDRON | 2004年 / 60卷 / 28期

基金：

日本学术振兴会;

关键词：

spirobenzopyran; crown ether; fluorescence emission; metal ion;

D O I：

10.1016/j.tet.2004.04.073

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxymethylcrowned spirobenzopyran 1 and pyrenylspirobenzopyran 2 were synthesized, and fluorescence emission of their corresponding merocyanine form was examined in the presence of metal ions. For 2, fluorescence emission derived from the pyrene moiety was completely quenched by photoinduced electron transfer (PET) of the nitrogen atom when the merocyanine form was not produced, namely, without metal ions. However, when 2 was converted to the merocyanine form by the complexation of its crown ether with a metal ion, fluorescence resonance energy transfer (FRET) from the pyrene to the merocyanine moieties took place to produce fluorescence emission. This result demonstrates that the spirobenzopyran isomerization can function as a fluorescence emission switch. Fluorescence quantum yield measurement for 1 and 2 showed that fluorescence emission depends on the binding metal ion in which the fluorescence quantum yield generally increased with the increase of metal ion radius. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：6029 / 6036

页数：8

共 41 条

[1] Chromened t-butylcalix[4]arenes:: cooperation effect of chromene and calixarene moieties on photochromism and metal-ion binding ability [J].