Novel blue emitting tetra- and pentamethylpiperidin-4-yloxy-1,8-naphthalimides as photoinduced electron transfer based sensors for transition metal ions and protons

被引:53
作者
Bojinov, Vladimir B. [1 ]
Panova, Ionka P. [1 ]
Chovelon, Jean-Marc [2 ]
机构
[1] Univ Chem Technol & Met, Dept Organ Synth, BU-1756 Sofia, Bulgaria
[2] Univ Lyon 1, CNRS, Inst Rech Catalyse & Environm Lyon IRCEYLON, UMR 5256, F-69626 Villeurbanne, France
基金
美国国家科学基金会;
关键词
1,8-Naphthalimide; Fluorescence; HALS; UV absorbers; Sensors; Photoinduced electron transfer; Phase transfer catalysis;
D O I
10.1016/j.snb.2008.08.016
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
Two novel blue emitting 1,8-naphthalimides (1 and 2), containing 2,2,6,6-tetramethylpiperidin-4-yloxy moieties, and newly synthesized under phase transfer catalysis conditions 4-(1,2,2,6,6-pentamethylpiperidin-4-yloxy)-1,8-naphthalimide 7, were configured as "fluorophore-spacer-receptor" systems. Basic photophysical characteristics of the novel fluorescent brighteners were investigated in both DMF and water/DMF (4:1, v/v) solution. Their ability to detect cations was evaluated in the presence of transition metal ions (Cu2+, Pb2+, Zn2+, Ni2+, CO2+) and protons. The presence of metal ions and protons was found to disallow a photoinduced electron transfer leading to an enhancement in the fluorophore emission intensity. The results clearly showed a good sensor activity towards transition metal ions and protons, especially of compound 7. containing tertiary amine receptor. This indicates the potential of the novel compounds as highly efficient "off-on" pH switchers and fluorescent detectors for metal ions. (c) 2008 Elsevier B.V. All rights reserved.
引用
收藏
页码:172 / 180
页数:9
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