XII Iberian Meeting of Electrochemistry XVI Meeting of the ...

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XII Iberian Meeting of Electrochemistry & XVI Meeting of the Portuguese Electrochemical Society PE 01 Some aspects of the electrochemical reduction of the herbicide imazamethabenz acid on mercury electrodes Sara Pintado Benzal, 1 Mercedes Ruiz Montoya and José Miguel Rodríguez Mellado 1 Departamento de Química Física y Termodinámica Aplicada. Universidad de Córdoba. Campus de Rabanales edificio Marie Curie 2ª planta (España) q02pibes@uco.es The knowledge of the electrochemical behaviour of pollutants can contribute to the development of methods able to eliminate such compounds or, at least, to decrease their toxicity. Other imidazolinone herbicides such as imazapyr, imazethapyr or imazaquin have been studied by the authors [1]. Imazamethabenz acid differs from these compounds in the aromatic part (a benzoic acid rest) that is non-reducible in aqueous media (scheme 1). So, the reducible part of the molecule must be the imidazolinone ring as found for imazamethabenz methyl [2] (a) (b) (c) Scheme 1: Structures of (a) imazapyr, (b) imazaquin, and (c) imazamethabenz acid Polarographic and voltammetric studies have been made on mercury electrodes from strongly acidic media (0.12.7 M H 2 SO 4 ) to pH 12. The overall reduction process involves the uptake of two electrons, the following species being reduced [2, 3]: C H 3 H O N N + CH CH3 H CH 3 O R 1 R 2 C OH -2H + 2H + C H 3 H O N N CH CH3 CH 3 O R 1 R 2 C O - - H + H + R 1 O N - R 2 H 3 C N CH CH3 C - CH 3 O O In strongly acidic media (pH
XII Iberian Meeting of Electrochemistry & XVI Meeting of the Portuguese Electrochemical Society PE 02 Electrochemical and Spectroelectrochemical Study of Alkyl-Substituted Heptathienoacenes C. Capel Ferrón a,b , B. Vercelli b , G. Zotti b , Mingqian He c , Weijun Niu c , V. Hernández a , J. T. López Navarrete a a Department of Physical Chemistry, Málaga University, 29071 Málaga (Spain) b Institute for Energetics and Interphases-IENI CNR, C.so Stati Uniti, 4, 35127 Padova (Italy) c Corning Incorporated, SP-FR-6, Corning, New York 14830 capel@uma.es Conjugated organic molecules such as pentacene have been widely used as organic field-effect transistor (OFET) materials. Oligothiophenes with complete ring fusion, are of particular interest due in part to their fully planar structure which avoids conformational disorder and more efficient molecular packing than usual oligothiophenes, they adopt face-to- face packing motifs in contrast to face-to-edge or herringbone packing commonly found in -linked oligothiophenes. Here we consider a series a serie of capped heptathienoacenes. [1] S S S S S 2D-7T S S H 3 C S S S CH 3 C 10 H 21 S S S S C 10 H 21 2D M-7T C 10 H 21 C10 H 21 S C 10 H 21 S S S C 10 H 21 C 10 H 21 S S S S C 10 H 21 4D-7T Si S S S S S T IPS-7T-T IPS S Si The occurrence of -dimerization in these flat thienoacenes upon oxidation has been checked with the 7T compounds bearing scarcely hindering C 10 H 21 - or CH 3 -moieties. The spectroelectrochemistry of 2D-7T, 2MD-7T and 4D-7T displays a broad band at ca. 700 nm assigned to the formation of -dimers, however the UV-Vis-NIR spectrum of TIPS-7T-TIPS upon oxidation at 700 mV exhibits two bands around 575 nm and 1028 nm, typical of insolated radical cations. The formation of -dimers in this oligomer is hindered by the bulky TIPS groups incorporated in its terminal alpha positions. [2] References [1] Mingqian He and Feixia Zhang , JOC, 2007, 72, 442-451. [2] J. Aragó; M. Viruela; E. Ortí; R. Malavé Osuna; B.Vercelli; G. Zotti; V. Hernández; J. T. López Navarrete; J. T. Henssler; A. J. Matzger; Y. Suzuki; and Shigehiro Yamaguchi, Chem. Eur. J., 2010, DOI: 10.1002/chem.200903343 September, 811, 2010. ISEL - Lisbon 93
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