Oligothiophene Tetracyanobutadienes: Alternative Donor-Acceptor Architectures for Molecular and Polymeric Materials
| Autor: | Juan Casado, Matthew D. Lovander, M. Carmen Ruiz Delgado, Deborah K. Schneiderman, Barbara Vercelli, Jon N. Bohnsack, Gianni Zotti, Lindsay M. Hinkle, Kent R. Mann, Ted M. Pappenfus, Juan T. López Navarrete |
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| Jazyk: | angličtina |
| Rok vydání: | 2011 |
| Předmět: |
chemistry.chemical_classification
Chemistry General Chemical Engineering General Chemistry Electron acceptor Tetracyanoethylene Photochemistry Redox Acceptor AMBIPOLAR ORGANIC SEMICONDUCTORS chemistry.chemical_compound TRICYANOVINYL-CAPPED OLIGOTHIOPHENES Intramolecular force Materials Chemistry Moiety Density functional theory Cyclic voltammetry FIELD-EFFECT TRANSISTORS |
| Zdroj: | Chemistry of materials 23 (2011): 823–831. doi:10.1021/cm102128g info:cnr-pdr/source/autori:Pappenfus T.M.; Schneiderman D.K.; Casado J.; Navarrete J.T.L.; Delgado M.C.R.; Zotti G.; Vercelli B.; Lovander M.D.; Hinkle L.M.; Bohnsack J.N.; Mann K.R./titolo:Oligothiophene Tetracyanobutadienes: Alternative Donor-Acceptor Architectures for Molecular and Polymeric Materials/doi:10.1021%2Fcm102128g/rivista:Chemistry of materials/anno:2011/pagina_da:823/pagina_a:831/intervallo_pagine:823–831/volume:23 |
| DOI: | 10.1021/cm102128g |
| Popis: | Oligothiophene-substituted 1,1,4,4-tetracyanobutadienes (TCBDs) have been synthesized by [2þ 2] cycloaddition reactions between tetracyanoethylene and oligothiophene alkynes. The TCBD moiety is compared to other electron acceptors attached to dibutylterthiophene including dicyanovinyl (DCV) and tricyanovinyl (TCV).These donor-acceptor molecules (TCBD-3T, DCV-3T, andTCV-3T) show red-shifted absorption spectra relative to the unsubstituted oligothiophene as a result of intramolecular charge-transfer (ICT). Monosubstituted terthiophenes bearing the electron acceptors show both oxidation and reduction processes as characterized by cyclic voltammetry. Density functional theory (DFT) calculations are used to explain the electronic and redox properties of the materials. Electrochemical oxidation of a bis(terthienyl)-substitutedTCBDmolecule (3T-TCBD-3T) yields a conducting polymer exhibiting balanced ambipolar redox conduction with similar values for the oxidized and reduced states of the polymer (1 _ 10-3 S cm-1). Raman spectra of the asymmetric donor-acceptor materials are characterized by two intense bands characteristic of the aromatic and quinoidal regions in the conjugated À-system of the oligothiophene. |
| Databáze: | OpenAIRE |
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