A chemodosimer based on a core-substituted naphthalene diimide for fluoride ion detection

被引：82
作者：
Buckland, Dale [1 ]
Bhosale, Sheshanath V. [1 ]
Langford, Steven J. [1 ]
机构：
[1] Monash Univ, Sch Chem, Clayton, Vic 3800, Australia
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 16期
基金：
澳大利亚研究理事会;
关键词：
Naphthalene diimide; Anion recognition; Naked-eye detection; UV-vis; Fluorescence; SELECTIVE FLUORESCENT; TRANSFER DYNAMICS; DEPROTONATION; SENSORS; WELL;
D O I：
10.1016/j.tetlet.2011.02.080
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We have demonstrated the use of a core-substituted naphthalene diimide (c-NDI) bearing trimethylsilyl-acetylene moieties which is capable of being utilised as a colorimetric and fluorescent chemodosimeter for anions. The detection of anions was carried out by desilylation of the detector. A significant change, visible to the naked eye, was observed only upon addition of F- ions; addition of other ions, such as Cl-, Br-, HSO4-, AcO- and H2PO4- resulted in no distinct changes. Modifications of the electronic properties of the c-NDI upon addition of fluoride ions were characterised by means of UV-vis, fluorescence and H-1 NMR spectroscopy. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1990 / 1992
页数：3
相关论文
共 35 条
[1]   Reactivities of carboxyalkyl-substituted 1,4,5,8-naphthalene diimides in aqueous solution [J].
Abraham, B ;
McMasters, S ;
Mullan, MA ;
Kelly, LA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4293-4300
[2]   Colorimetric 'naked-eye' and fluorescent sensors for anions based on amidourea functionalised 1,8-naphthalimide structures: anion recognition via either deprotonation or hydrogen bonding in DMSO [J].
Ali, Haslin Dato Paduka ;
Kruger, Paul E. ;
Gunnlaugsson, Thorfinnur .
NEW JOURNAL OF CHEMISTRY, 2008, 32 (07) :1153-1161
[3]   Wavelength-ratiometric probes for the selective detection of fluoride based on the 6-aminoquinolinium nucleus and boronic acid moiety [J].
Badugu, R ;
Lakowicz, JR ;
Geddes, CD .
JOURNAL OF FLUORESCENCE, 2004, 14 (06) :693-703
[4]   Ultrafast excited-state dynamics of strongly coupled porphyrin/core-substituted-naphthalenediimide dyads [J].
Banerji, Natalie ;
Bhosale, Sheshanath V. ;
Petkova, Irina ;
Langford, Steven J. ;
Vauthey, Eric .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2011, 13 (03) :1019-1029
[5]   Synthesis and Photophysics of Core-Substituted Naphthalene Diimides: Fluorophores for Single Molecule Applications [J].
Bell, Toby D. M. ;
Yap, Sheryll ;
Jani, Chintan H. ;
Bhosale, Sheshanath V. ;
Hofkens, Johan ;
De Schryver, Frans C. ;
Langford, Steven J. ;
Ghiggino, Kenneth P. .
CHEMISTRY-AN ASIAN JOURNAL, 2009, 4 (10) :1542-1550
[6]   Photoproduction of proton gradients with π-stacked fluorophore scaffolds in lipid bilayers [J].
Bhosale, Sheshanath ;
Sisson, Adam L. ;
Talukdar, Pinaki ;
Fuerstenberg, Alexandre ;
Banerji, Natalie ;
Vauthey, Eric ;
Bollot, Guillaume ;
Mareda, Jiri ;
Roger, Cornelia ;
Wuerthner, Frank ;
Sakai, Naomi ;
Matile, Stefan .
SCIENCE, 2006, 313 (5783) :84-86
[7]   Chemistry of naphthalene diimides [J].
Bhosale, Sheshanath V. ;
Jani, Chintan H. ;
Langford, Steven J. .
CHEMICAL SOCIETY REVIEWS, 2008, 37 (02) :331-342
[8]   Solvophobic control of core-substituted naphthalene diimide nanostructures [J].
Bhosale, Sheshanath V. ;
Jani, Chintan ;
Lalander, Cecilia H. ;
Langford, Steven J. .
CHEMICAL COMMUNICATIONS, 2010, 46 (06) :973-975
[9]   The synthesis of novel core-substituted naphthalene diimides via Suzuki cross-coupling and their properties [J].
Bhosale, Sheshanath V. ;
Kalyankar, Mohan B. ;
Bhosale, Sidhanath V. ;
Langford, Steven J. ;
Reid, Ellen F. ;
Hogan, Conor F. .
NEW JOURNAL OF CHEMISTRY, 2009, 33 (12) :2409-2413
[10]   RETRACTED: A Core-Substituted Naphthalene Diimide Fluoride Sensor (Retracted Article) [J].
Bhosale, Sheshanath V. ;
Bhosale, Sidhanath V. ;
Kalyankar, Mohan B. ;
Langford, Steven J. .
ORGANIC LETTERS, 2009, 11 (23) :5418-5421
1234