Premium
Multi‐Channel Receptors and Their Relation to Guest Chemosensing and Reconfigurable Molecular Logic Gates
Author(s) -
Jiménez Diego,
MartínezMáñez Ramón,
Sancenón Félix,
RosLis José V.,
Soto Juan,
Benito Ángel,
GarcíaBreijo Eduardo
Publication year - 2005
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.200400844
Subject(s) - chemistry , acetonitrile , moiety , hypsochromic shift , redox , electrochemistry , fluorescence , chromophore , metal , stereochemistry , photochemistry , medicinal chemistry , inorganic chemistry , electrode , organic chemistry , physics , quantum mechanics
The synthesis and characterisation of a family of multi‐channel receptors containing crown‐cation binding sites anchored to a 1‐aminophenyl‐1,2,2‐tricyanoethylene group is reported. The ligands L 1 –L 6 bear a 1‐aminophenyl‐1,2,2‐tricyanoethylene scaffolding which is simultaneously a redox‐active group (showing reduction processes at moderately modest potentials) and an acceptor moiety in the 1‐aminophenyl‐1,2,2‐tricyanoethylene chromophore. Additionally, dyes L 1 –L 6 also show fluorescence emission. The colour variation of L 1 –L 6 in acetonitrile in the presence of the metal cations Ag + , Cd 2+ , Cu 2+ , Fe 3+ , Hg 2+ , Pb 2+ and Zn 2+ has been studied. Selective hypsochromic shifts were found for the systems L 4 ‐Pb 2+ , L 5 ‐Hg 2+ and L 6 ‐Hg 2+ . For Hg 2+ with L 5 and L 6 and Pb 2+ with L 4 , emission fluorescence enhancements most likely associated with metal coordination to the anilinium nitrogen were observed. The electrochemical behaviour of receptors L 1 –L 6 was studied in acetonitrile with platinum as working electrode and [Bu 4 N][BF 4 ] as supporting electrolyte. This family of receptors shows a one‐electron reversible reduction process at around –0.70 V vs. SCE, attributed to the reduction of the tricyanovinyl group. Additionally, all the receptors also show the oxidation of the anilinium moiety at about 1.2–1.4 V vs. SCE. Significant anodic shifts of both reduction and oxidation waves were found in the presence of certain metal cations. The relationship of these multiple‐channel signalling receptors with guest chemosensing and reconfigurable molecular‐based logic gates is discussed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)