A novel blue fluorescent 4-(1,2,2,6,6-pentamethylpiperidin-4-yloxy)-1,8-naphthalimide pH chemosensor based on photoinduced electron transfer

被引:41
作者
Bojinov, Vladimir B.
Simeonov, Danail B.
Georgiev, Nikolai I.
机构
[1] Univ Chem Technol & Met, Dept Organ Synth, BU-1756 Sofia, Bulgaria
[2] Bulgarian Acad Sci, Inst Inorgan Chem, BU-1113 Sofia, Bulgaria
基金
美国国家科学基金会;
关键词
4-oxy-1,8-naphthalimide; blue fluorescence; 2,2,6,6-tetramethylpiperidine; 1,2,2,6,6-pentamethylpiperidine; optical sensor; pH sensing; photoinduced electron transfer;
D O I
10.1016/j.dyepig.2006.08.006
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Three, blue emitting 2,2,6,6- tetramethylpiperidin-4-yloxy-1, 8-naphthalimides 1-3 were configured as "fluorophore-spacer-receptor" systems. The photophysical characteristics of the dyes were investigated in water/DMF (4: 1, v/v) solution. 1,8-Naphthalimide 1, which lacks the "lower" amino receptor, and compound 2, containing a secondary amino receptor at 1,8-naphthalimide 4-oxy moiety, did not show significant changes in emission properties as a function of pH. In contrast to compounds 1 and 2, 4-(1,2,2,6,6-pentamethylpiperidin-4-yloxy)- 1,8-naphthalimide 3 displayed "on-off" switching in its fluorescence over a wider pH scale. From the luminescent changes pK(a) value of 8.63 was determined. This indicates that the chemosensor 3 would be able to act as highly efficient "off-on" fluorescent switcher for pH. (C) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:41 / 46
页数:6
相关论文
共 66 条
[11]   Metal complexes as components of luminescent signalling systems [J].
de Silva, AP ;
Fox, DB ;
Huxley, AJM ;
McClenaghan, ND ;
Roiron, J .
COORDINATION CHEMISTRY REVIEWS, 1999, 185-6 :297-306
[12]   A MOLECULAR PHOTOIONIC AND GATE BASED ON FLUORESCENT SIGNALING [J].
DE SILVA, AP ;
GUNARATNE, HQN ;
MCCOY, CP .
NATURE, 1993, 364 (6432) :42-44
[13]   Combining luminescence, coordination and electron transfer for signalling purposes [J].
de Silva, AP ;
Fox, DB ;
Huxley, AJM ;
Moody, TS .
COORDINATION CHEMISTRY REVIEWS, 2000, 205 :41-57
[14]  
de Silva AP, 1999, CHEM COMMUN, P163
[15]   The pH-dependent fluorescence of pyridylmethyl-4-amino-1,8-naphthalimides [J].
de Silva, AP ;
Goligher, A ;
Gunaratne, HQN ;
Rice, TE .
ARKIVOC, 2003, :229-243
[16]   NEW FLUORESCENT MODEL COMPOUNDS FOR THE STUDY OF PHOTOINDUCED ELECTRON-TRANSFER - THE INFLUENCE OF A MOLECULAR ELECTRIC-FIELD IN THE EXCITED-STATE [J].
DE SILVA, AP ;
GUNARATNE, HQN ;
HABIBJIWAN, JL ;
MCCOY, CP ;
RICE, TE ;
SOUMILLION, JP .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1995, 34 (16) :1728-1731
[17]   Signaling recognition events with fluorescent sensors and switches [J].
de Silva, AP ;
Gunaratne, HQN ;
Gunnlaugsson, T ;
Huxley, AJM ;
McCoy, CP ;
Rademacher, JT ;
Rice, TE .
CHEMICAL REVIEWS, 1997, 97 (05) :1515-1566
[18]  
De Souza MM, 2002, PHARMAZIE, V57, P430
[19]  
DESILVA AP, 2003, J CHEM SOC DA, V10, P1902
[20]   REFERENCE MATERIALS FOR FLUORESCENCE MEASUREMENT [J].
EATON, DF .
PURE AND APPLIED CHEMISTRY, 1988, 60 (07) :1107-1114