N-acylureido functionality as acceptor substituent in solvatochromic fluorescence probes: Detection of carboxylic acids, alcohols, and fluoride ions

被引：62
作者：
Bohne, C
Ihmels, H [1 ]
Waidelich, M
Yihwa, C
机构：
[1] Univ Siegen, Inst Organ Chem, D-57072 Siegen, Germany
[2] Univ Victoria, Dept Chem, Victoria, BC V8W 3V6, Canada
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 49期
关键词：
D O I：
10.1021/ja052262c
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
N,N′-Dicyclohexyl-N-(6′-methoxyanthryl-2-carbonyl)urea (1a) exhibits a strong solvatochromism with respect to its fluorescence properties. The emission maxima of 1a correlate well with the anion-stabilizing properties of the solvent. This feature allows the detection of analytes with high acceptor numbers, such as alcohols and carboxylic acids, and the detection of analytes such as fluoride ions which form strong hydrogen bonds with the amido hydrogen atom. Copyright © 2005 American Chemical Society.
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页码：17158 / 17159
页数：2
相关论文
共 24 条
[1]  
Beer PD, 2001, ANGEW CHEM INT EDIT, V40, P486, DOI 10.1002/1521-3773(20010202)40:3<486::AID-ANIE486>3.3.CO
[2]  
2-G
[3]   Synthesis of coumarin-3-O-acylisoureas by different carbodiimides [J].
Bonsignore, L ;
Cottiglia, F ;
Lavagna, SM ;
Loy, G ;
Secci, D .
HETEROCYCLES, 1999, 50 (01) :469-478
[4]   SYNTHESIS OF COUMARIN-3-O-ACYLISOUREAS BY DICYCLOHEXYLCARBODIIMIDE [J].
BONSIGNORE, L ;
COTTIGLIA, F ;
MACCIONI, AM ;
SECCI, D ;
LAVAGNA, SM .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (02) :573-577
[5]   Formal intramolecular [5+2] photocycloaddition reactions of maleimides: A novel approach to the CDE ring skeleton of (-)-cephalotaxine [J].
Booker-Milburn, KI ;
Dudin, LF ;
Anson, CE ;
Guile, SD .
ORGANIC LETTERS, 2001, 3 (19) :3005-3008
[6]  
DESVERGNE JP, 1997, CHEMOSENSORS ION MOL, V97, P1515
[7]   AN UNEXPECTEDLY STRONG HYDROGEN-BOND - ABINITIO CALCULATIONS AND SPECTROSCOPIC STUDIES OF AMIDE-FLUORIDE SYSTEMS [J].
EMSLEY, J ;
JONES, DJ ;
MILLER, JM ;
OVERILL, RE ;
WADDILOVE, RA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (01) :24-28
[8]   Anthryl-substituted heterocycles as acid-sensitive fluorescence probes [J].
Ihmels, H ;
Meiswinkel, A ;
Mohrschladt, CJ ;
Otto, D ;
Waidelich, M ;
Towler, M ;
White, R ;
Albrecht, M ;
Schnurpfeil, A .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) :3929-3938
[9]  
Ihmels H, 1999, EUR J ORG CHEM, V1999, P1595
[10]   Novel fluorescence probes based on 2,6-donor-acceptor-substituted anthracene derivatives [J].
Ihmels, H ;
Meiswinkel, A ;
Mohrschladt, CJ .
ORGANIC LETTERS, 2000, 2 (18) :2865-2867
123