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

被引:61
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
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.
引用
收藏
页码:17158 / 17159
页数:2
相关论文
共 24 条
[11]  
LAKOWICZ JR, 1999, PRINCIPLES FLUORESCE, pCH6
[12]  
LINERT W, 1993, J CHEM SOC P2, V2, P1415
[13]   DIPOLMOMENT UND ELEKTRONENSTRUKTUR VON ANGEREGTEN MOLEKULEN [J].
LIPPERT, E .
ZEITSCHRIFT FUR NATURFORSCHUNG PART A-ASTROPHYSIK PHYSIK UND PHYSIKALISCHE CHEMIE, 1955, 10 (07) :541-545
[14]   Fluorogenic and chromogenic chemosensors and reagents for anions [J].
Martínez-Máñez, R ;
Sancenón, F .
CHEMICAL REVIEWS, 2003, 103 (11) :4419-4476
[15]   SOLVENT EFFECTS UPON FLUORESCENCE SPECTRA AND THE DIPOLEMOMENTS OF EXCITED MOLECULES [J].
MATAGA, N ;
KAIFU, Y ;
KOIZUMI, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1956, 29 (04) :465-470
[16]   Fluorescence of organic molecules in chiral recognition [J].
Pu, L .
CHEMICAL REVIEWS, 2004, 104 (03) :1687-1716
[17]   SOLVATOCHROMIC DYES AS SOLVENT POLARITY INDICATORS [J].
REICHARDT, C .
CHEMICAL REVIEWS, 1994, 94 (08) :2319-2358
[18]  
Reichardt C., 2003, SOLVENTS SOLVENT EFF
[19]   Intramolecular hydrogen bonding in the S1(ππ*) excited state of anthranilic acid and salicylic acid:: TDDFT calculation of excited-state geometries and infrared spectra [J].
Sobolewski, AL ;
Domcke, W .
JOURNAL OF PHYSICAL CHEMISTRY A, 2004, 108 (49) :10917-10922
[20]  
SUPPAN P, 1997, SALVATOCHROMISM