Synthesis and fluorescence studies of novel bis(azacrown ether) type chemosensors containing an acridinone unit

被引：10
|
作者：
Moczar, Ildiko [1 ]
Peragovics, Agnes [2 ]
Baranyai, Peter [3 ]
Toth, Klara [4 ,5 ]
Huszthy, Peter [1 ,2 ]
机构：
[1] Hungarian Acad Sci, Res Grp Alkaloid Chem, H-1521 Budapest, Hungary
[2] Budapest Univ Technol & Econ, Dept Organ Chem & Technol, H-1521 Budapest, Hungary
[3] Hungarian Acad Sci, Chem Res Ctr, H-1525 Budapest, Hungary
[4] Budapest Univ Technol & Econ, Dept Inorgan & Analyt Chem, H-1521 Budapest, Hungary
[5] Hungarian Acad Sci, Res Grp Tech Analyt Chem, H-1521 Budapest, Hungary
来源：
TETRAHEDRON | 2010年 / 66卷 / 16期
基金：
匈牙利科学研究基金会;
关键词：
Azacrown ethers; Acridinones; Fluorescent chemosensors; Metal ion recognition; Photoinduced electron transfer; Fluorescence spectroscopy; OPTICAL CHARACTERIZATION; AZACROWN ETHERS; RECOGNITION; SENSORS; BINDING; IONS; ACRIDONO-18-CROWN-6; SWITCHES; LIGANDS; EVENTS;
D O I：
10.1016/j.tet.2010.02.076
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Three new bis(azacrown ether)s containing an acridinone fluorescent signalling unit were prepared by reacting 9-chloro-4,5-bis(chloromethyl)acridine with monoazacrown ethers with different cavity sizes followed by a hydrolysis step. Their fluorescent characteristics and the complexation properties of the one containing two monoaza-18-crown-6 ether receptors towards selected metal ions were studied. The operation of the latter ligand is based on the photoinduced electron transfer (PET) process, thus it shows fluorescence enhancement in the presence of metal ions. Since the sensor molecule contains two receptor moieties, it is able to form two types of complex with 1:1 and 1:2 ligand to metal ion ratios, which have different emission spectra. The reason for this spectral difference may be that the 1:1 complex is a sandwich type one in which the acridinone unit can undergo structural changes. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2953 / 2960
页数：8
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