Tetrathiafulvalene-imine-pyridine assemblies for Pb2+ recognition

被引：44
作者：
Balandier, Jean-Yves [1 ]
Belyasmine, Ahmed [1 ]
Salle, Marc [1 ]
机构：
[1] Univ Angers, Lab Chim & Ingn Mol Materiaux Angers, CNRS, UMR 6200, F-49045 Angers, France
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 02期
关键词：
N ligands; charge transfer; conjugation; imines; donor-acceptors systems;
D O I：
10.1002/ejoc.200700705
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of donor-pi-acceptor systems incorporating a tetrathiafulvalene moiety as the donating unit have been designed and synthesized. The efficiency of the imine (-C=N-) bond as a conjugated pi-linker in promoting intramolecular charge transfer is demonstrated and supported by calculations at the B3LYP/6-31G(d,p) level of theory. This property has been explored in the case of pyridyl-substituted systems which exhibit in particular a high binding affinity and selectivity for Ph2+ (logK = 3.5 in CH2Cl2/CH3CN), as shown by UV/Vis and H-1 NMR titrations as well as by remarkable colorimetric and electrochemical signaling. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).
引用
收藏
页码：269 / 276
页数：8
相关论文
共 80 条
[1]   ELECTRONIC-STRUCTURES AND CONFORMATIONS OF N-BENZYLIDENEANILINES .1. ELECTRONIC ABSORPTION SPECTRAL STUDY COMBINED WITH CNDO-S CI CALCULATIONS [J].
AKABA, R ;
TOKUMARU, K ;
KOBAYASHI, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1980, 53 (07) :1993-2001
[2]   (E)-4-[2-(bis(octadecylsulfanyl)tetrathiafulvalenyl)ethenyl]-1-methylpyridinium iodide:: synthesis and characterisation of its Langmuir-Blodgett films [J].
Andreu, R ;
Garín, J ;
Orduna, J ;
Ashwell, GJ ;
Amiri, MA ;
Hamilton, R .
THIN SOLID FILMS, 2002, 408 (1-2) :236-239
[3]  
Andreu R, 2000, EUR J ORG CHEM, V2000, P737, DOI 10.1002/(SICI)1099-0690(200003)2000:5<737::AID-EJOC737>3.0.CO
[4]  
2-6
[5]  
[Anonymous], 2003, GAUSSIAN 03 REVISION
[6]   Intramolecular charge-transfer interactions in π-extended tetrathiafulvalene derivatives [J].
Aqad, E ;
Lakshmikantham, MV ;
Cava, MP ;
Metzger, RM ;
Khodorkhovsky, V .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (03) :768-775
[7]   New versatile building block for the construction of tetrathiafulvalene-based donor-acceptor systems [J].
Baffreau, J ;
Dumur, F ;
Hudhomme, P .
ORGANIC LETTERS, 2006, 8 (07) :1307-1310
[8]  
BATAIL P, MOL CONDUCTORS
[9]   Divalent transition metal complexes of alkylpyridyl derivatized dmit ligands [J].
Becher, J ;
Hazell, A ;
McKenzie, CJ ;
Vestergaard, C .
POLYHEDRON, 2000, 19 (06) :665-672
[10]   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
12345678