An exploration of ferrocenyl ureas as enantioselective electrochemical sensors for chiral carboxylate anions

被引：68

作者：

Willener, Yasmine ^{[2
]}

Joly, Kevin A. ^{[1
]}

Moody, Christopher J. ^{[1
]}

Tucker, James H. R. ^{[2
]}

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

[2] Univ Birmingham, Sch Chem, Birmingham B15 2TT, W Midlands, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 04期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1021/jo701809b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The syntheses of a series of chiral ureas containing the redox-active ferrocene group are described. Each of these bind chiral carboxylates in organic solvents through hydrogen-bonding interactions, as evidenced by spectroscopic and cyclic voltammetry measurements, the latter allowing these guests to be electrochemically sensed in solution. The enantioselectivity in the complexation of the protected amino acid N-benzenesulfonylproline by a ferrocenylbenzyl host is high enough to allow opposite enantiomers to be distinguished by electrochemical means.

引用

页码：1225 / 1233

页数：9

共 31 条

[1] Electrochemical recognition of chiral species using quaternary ammonium binaphthyl salts [J].

Abbott, AP ;

Barker, GW ;

Davies, DL ;

Griffiths, GA ;

Walter, AJ ;

Kocovsky, P .

ANALYTICAL CHEMISTRY, 2002, 74 (16) :4002-4006

[2]

ALAVOINE GGA, 1991, J ORGANOMET CHEM, V412, P381

[3] Assembly of dendrimers with redox-active [{CpFe(μ3-CO)}4] clusters at the periphery and their application to oxo-anion and adenosine-5′-triphosphate sensing [J].

Aranzaes, JR ;

Belin, C ;

Astruc, D .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (01) :132-136

[4] Electrochemically controlled hydrogen bonding. Nitrobenzenes as simple redox-dependent receptors for arylureas [J].

Bu, JJ ;

Lilienthal, ND ;

Woods, JE ;

Nohrden, CE ;

Hoang, KT ;

Truong, D ;

Smith, DK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (17) :6423-6429

[5] Anion recognition and redox sensing by a metalloporphyrin-ferrocene-alkylammonium conjugate [J].

Bucher, C ;

Devillers, CH ;

Moutet, JC ;

Royal, G ;

Saint-Aman, E .

NEW JOURNAL OF CHEMISTRY, 2004, 28 (12) :1584-1589

[6] Structure-selective recognition by voltammetry: Enantiomeric determination of amines using azophenolic crowns in aprotic solvent [J].

Chun, Kyungmin ;

Kim, Tae Hyun ;

Lee, One-Sun ;

Hirose, Keiji ;

Chung, Taek Dong ;

Chung, Doo Soo ;

Kim, Hasuck .

ANALYTICAL CHEMISTRY, 2006, 78 (21) :7597-7600

[7]

Connors K. A., 1987, BINDING CONSTANTS ME

[8] Rigidified tripodal chiral ligands in the asymmetric recognition of amino compounds [J].

Dai, ZH ;

Xu, XD ;

Canary, JW .

CHIRALITY, 2005, 17 :S227-S233

[9] Binding of amino acids into a novel multiresponsive ferrocene receptor having an ene backbone [J].

Debroy, P ;

Banerjee, M ;

Prasad, M ;

Moulik, SP ;

Roy, S .

ORGANIC LETTERS, 2005, 7 (03) :403-406

[10] Synthetic receptors for carboxylic acids and carboxylates [J].

Fitzmaurice, RJ ;

Kyne, GM ;

Douheret, D ;

Kilburn, JD .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (07) :841-864

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