Fluorescent 4-(2,2,6,6-tetramethylpiperidin-4-ylamino)-1,8-naphthalimide pH chemosensor based on photoinduced electron transfer

被引:68
作者
Bojinov, Vladimir B. [1 ]
Konstantinova, Temenushka N. [1 ]
机构
[1] Univ Chem Technol & Met, Dept Organ Synth, BU-1756 Sofia, Bulgaria
基金
美国国家科学基金会;
关键词
4-amino-1,8-naphthalimide; 2,2,6,6-tetramethylpiperidine; fluorescence; optical sensor; pH sensing; photoinduced electron transfer (PET);
D O I
10.1016/j.snb.2006.10.035
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
Two isomeric 2,2,6,6-tetramethylpiperidinyl-4-amino-1,8-naphthalimides 5 and 7 were configured as "fluorophore-spacer-receptor" systems. Photophysical characteristics of the dyes were investigated in water/DMF (4:1, v/v) solution. Compound 5, which lacks the amino receptor at the 1,8-naphthalimide 4-amino moiety, did not show any changes in the emission properties as a function of pH. In contrast to compound 5, 4-(2,2,6, 6-tetramethylpiperidin-4-ylami no) - 1, 8 -naphthalimide 7 displayed "on-off' switching in its fluorescence as a function of pH. From the luminescent changes pK(a) value of 8. 18 was determined. This indicates that the chemosensor 7 would be able to act as highly efficient "off-on" fluorescent switcher for pH. (C) 2006 Elsevier B.V. All rights reserved.
引用
收藏
页码:869 / 876
页数:8
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