Origins of 'on-off' fluorescent behavior of 8-hydroxyquinoline containing chemosensors

被引:90
作者
Bronson, RT
Montalti, M
Prodi, L
Zaccheroni, N
Lamb, RD
Dalley, NK
Izatt, RM
Bradshaw, JS
Savage, PB
机构
[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
[2] Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA
关键词
chemosensor; fluorescence; photophysical; general base; quinoline;
D O I
10.1016/j.tet.2004.08.062
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Derivatives of 8-hydroxyquinoline were used as model compounds to probe the pathways of non-radiative relaxation of fluorophores in two fluorescent chemosensors. Results suggest that both photo-induced proton transfer and photo-induced electron transfer contribute to quenching the fluorescence of the chemosensors. Crystal structures of an 8-hydroxyquinoline-containing chemosensor complexed to various metal ions indicate that a proton shift occurs concomitant with complex formation. This proton shift precludes both photo-induced proton and electron transfer allowing fluorescence emission from chemosensor-metal ion complexes. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:11139 / 11144
页数:6
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