Highly effective electrochemical anion sensing based on oxoporphyrinogen

被引:25
作者
Schumacher, Amy Lea [2 ]
Hill, Jonathan P. [1 ]
Ariga, Katsuhiko [1 ]
D'Souza, Francis [2 ]
机构
[1] Natl Inst Mat Sci, Adv Mat Lab, Supermol Grp, Tsukuba, Ibaraki 3050044, Japan
[2] Wichita State Univ, Dept Chem, Wichita, KS 67260 USA
基金
美国国家科学基金会;
关键词
electrochemical anion sensing; porphyrinogen; cathodic shift; recognition;
D O I
10.1016/j.elecom.2007.09.010
中图分类号
O646 [电化学、电解、磁化学];
学科分类号
081704 ;
摘要
The effect of anion binding on the oxidation potential of an anion receptor, N-21,N-23-dibenzyl-5,10,15,20-(3,5-di-t-butyl-4-oxo-cyclohexa-2,5-dienylidene)porphyrinogen, 1 in o-dichlorobenzene is reported. The anion binding site of 1, at its inner pyrrolic amine hydrogens, is an integral part of the highly conjugated macrocycle, thus predicting larger potential shifts upon anion binding. Accordingly, cathodic shifts up to 600 mV are observed upon anion binding and such potential shifts correlate well with the anion binding constants. (C) 2007 Elsevier B.V. All rights reserved.
引用
收藏
页码:2751 / 2754
页数:4
相关论文
共 26 条
[1]  
Adams RLP, 1986, BIOCH NUCL ACIDS, P287
[2]  
[Anonymous], PORPHYRIN HDB
[3]   Mechanisms of electrochemical recognition of cations, anions and neutral guest species by redox-active receptor molecules [J].
Beer, PD ;
Gale, PA ;
Chen, GZ .
COORDINATION CHEMISTRY REVIEWS, 1999, 185-6 :3-36
[4]  
Beer PD, 2001, ANGEW CHEM INT EDIT, V40, P486, DOI 10.1002/1521-3773(20010202)40:3<486::AID-ANIE486>3.3.CO
[5]  
2-G
[6]   Electrochemical molecular recognition: pathways between complexation and signalling [J].
Beer, PD ;
Gale, PA ;
Chen, GZ .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1999, (12) :1897-1909
[7]  
Bianchi A, 1997, SUPRAMOLECULAR CHEMISTRY OF ANIONS, P217
[8]   Sulfate selective anion recognition by a novel tetraimidazolium zinc metalloporphyrin receptor [J].
Cormode, David P. ;
Murray, Sean S. ;
Cowley, Andrew R. ;
Beer, Paul D. .
DALTON TRANSACTIONS, 2006, (43) :5135-5140
[9]   Calix[4]pyrroles: Old yet new anion-binding agents [J].
Gale, PA ;
Sessler, JL ;
Kral, V ;
Lynch, V .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (21) :5140-5141
[10]   Fluoride ion receptors based on dipyrrolyl derivatives bearing electron-withdrawing groups: Synthesis, optical and electrochemical sensing, and computational studies [J].
Ghosh, T ;
Maiya, BG ;
Wong, MW .
JOURNAL OF PHYSICAL CHEMISTRY A, 2004, 108 (51) :11249-11259