A concave fluorescent sensor for anions based on 6-methoxy-1-methylquinolinium

被引：43

作者：

Amendola, V ^{[1
]}

Fabbrizzi, L ^{[1
]}

Monzani, E ^{[1
]}

机构：

[1] Univ Pavia, Dipartimento Chim Gen, I-27100 Pavia, Italy

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2004年 / 10卷 / 01期

关键词：

anions; fluorescence spectroscopy; molecular recognition; receptors; sensors;

D O I：

10.1002/chem.200305338

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The ligand 2, in which three fluorogenic 6-methoxy-1-methylquinolinium fragments are appended to a mesityl platform, in MeCN forms 1:1 adducts with halides and other inorganic anions. H-1 NMR studies and molecular modelling indicate that 2 provides a cavity for anion inclusion and establishes electrostatic interactions with the guest. Anion inclusion induces quenching of the fluorogenic fragments with an efficiency decreasing along the series Br(-)much greater thanI(-)>NCS(-)much greater thanCl(-)>NO3-> HSO4-. The fluorimetric response of 2 to anions is orders of magnitude more sensitive than that of just 6-methoxy-1-methylquinolinium, ligand 1.

引用

页码：76 / 82

页数：7

共 13 条

[1] Anion sensing 'venus flytrap' hosts: a modular approach
Abouderbala, LO
Belcher, WJ
Boutelle, MG
Cragg, PJ
Dhaliwal, J
Fabre, M
Steed, JW
Turner, DR
Wallace, KJ
[J]. CHEMICAL COMMUNICATIONS, 2002, (04) : 358 - 359
[2] Bianchi A, 1997, SUPRAMOLECULAR CHEMISTRY OF ANIONS, P217
[3] Investigation of equilibria in solution. Determination of equilibrium constants with the HYPERQUAD suite of programs
Gans, P
Sabatini, A
Vacca, A
[J]. TALANTA, 1996, 43 (10) : 1739 - 1753
[4] Chloride-sensitive fluorescent indicators
Geddes, CD
Apperson, K
Karolin, J
Birch, DJS
[J]. ANALYTICAL BIOCHEMISTRY, 2001, 293 (01) : 60 - 66
[5] *HYP INC, HYP 6 0 MOL MOD SYST
[6] Quenching mechanism of quinolinium-type chloride-sensitive fluorescent indicators
Jayaraman, S
Verkman, AS
[J]. BIOPHYSICAL CHEMISTRY, 2000, 85 (01) : 49 - 57
[7] Artificial organic host molecules for anions
Schmidtchen, FP
Berger, M
[J]. CHEMICAL REVIEWS, 1997, 97 (05) : 1609 - 1646
[8] ANION-INDUCED FLUORESCENCE QUENCHING OF AROMATIC-MOLECULES
SHIZUKA, H
NAKAMURA, M
MORITA, T
[J]. JOURNAL OF PHYSICAL CHEMISTRY, 1980, 84 (09) : 989 - 994
[9] VALEUR B, 2002, MOL FLUORESCENCE PRI, P73
[10] VALEUR B, 2002, MOL FLUORESENCE PRIN

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