Oxidation Pathways Involving a Sulfide-Endcapped Donor-Acceptor-Donor π-Conjugated Molecule and Antimony(V) Chloride
| Autor: | Matthias Zeller, Sean M. Ryno, Jianguo Mei, Saadia T. Chaudhry, Chad Risko, David R. McMillin |
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| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Ketone 010304 chemical physics Sulfide chemistry.chemical_element 010402 general chemistry Electrochemistry 01 natural sciences Chloride Medicinal chemistry 0104 chemical sciences Surfaces Coatings and Films Adduct Antimony chemistry Oxidation state Nucleophilic aromatic substitution 0103 physical sciences Materials Chemistry medicine Physical and Theoretical Chemistry medicine.drug |
| Zdroj: | The journal of physical chemistry. B. 123(17) |
| ISSN: | 1520-5207 |
| Popis: | The oxidation pathways and products of a discrete, sulfide-endcapped donor–acceptor–donor (D/A/D) molecule, namely, propylenedioxythiophene–benzothiadiazole–propylenedioxythiophene, are investigated. The electrochemical and chemical oxidations proceed by two distinct routes. Specifically, electrochemical oxidation undergoes a sequential two-step, one-electron (1e–) oxidation route with a 117 mV difference between consecutive half-wave potentials. In contrast, chemical oxidation by antimony(V) chloride (SbCl5) causes the generation of four different oxidized species: (a) the 1e– oxidation state, (b) a decomposition product, (c) the 2e– oxidation state, and (d) a chloride adduct of the 2e– oxidation state. The decomposition product is generated by the reaction of the 1e– oxidation state with residual water, resulting in nucleophilic aromatic substitution at the sulfide group terminal positions. This reaction leads to the formation of a 2e– oxidized, oxygen atom (ketone) terminated decomposed molecule. The c... |
| Databáze: | OpenAIRE |
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