Synthesis and Electrochemical properties of Tetrasubstituted Tetraphenylethenes

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2006
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Schreivogel, Alina
Maurer, Jörg
Baro, Angelika
Laschat, Sabine
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European Journal of Organic Chemistry. 2006, 2006(15), pp. 3395-3404. ISSN 1434-193X. Available under: doi: 10.1002/ejoc.200600123
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Tetrakis(4-acetoxyphenyl and 4-benzoyloxyphenyl)ethenes 1f and 1g were obtained by acylation of tetrakis(4-hydroxyphenyl)ethene 1b. Ullmann etherification of 4,4′-dihydroxybenzophenone 2b and subsequent McMurry coupling yielded tetrakis(phenoxyphenyl)ethene 1i. The tetrakis(acetamidophenyl)ethene 1h was prepared in three steps from tetraphenylethene 1c by nitration, Raney-Ni reduction and subsequent acetylation. Alternatively, trifluoroacetamide 1j, 2-methylhexanamide 1k and 2,4-dimethylbenzamide 1l, with less tendency to form 2D hydrogen bonding networks and thus increased solubility as compared to 1h, were prepared by acylation of 4,4′-diaminobenzophenone 2a and subsequent McMurry coupling. Compounds 1f–l were investigated by cyclic voltammetry. While the phenyl ether derivative 1i displays single-electron processes during oxidation, a two-electron process was discovered for trifluoroacetamide 1j as was also supposed for the esters 1f and 1g. In addition, comproportionation constants were shown to be dependent on the solvent. In situ IR spectroelectrochemistry provided evidence for quinoidal type substructures in the dioxidized forms of tetraphenylethenes 1.

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540 Chemie
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Cyclic voltammetry / McMurry reaction, Spectroelectrochemistry, Tetraphenylethenes
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ISO 690SCHREIVOGEL, Alina, Jörg MAURER, Rainer F. WINTER, Angelika BARO, Sabine LASCHAT, 2006. Synthesis and Electrochemical properties of Tetrasubstituted Tetraphenylethenes. In: European Journal of Organic Chemistry. 2006, 2006(15), pp. 3395-3404. ISSN 1434-193X. Available under: doi: 10.1002/ejoc.200600123
BibTex
@article{Schreivogel2006Synth-13803,
  year={2006},
  doi={10.1002/ejoc.200600123},
  title={Synthesis and Electrochemical properties of Tetrasubstituted Tetraphenylethenes},
  number={15},
  volume={2006},
  issn={1434-193X},
  journal={European Journal of Organic Chemistry},
  pages={3395--3404},
  author={Schreivogel, Alina and Maurer, Jörg and Winter, Rainer F. and Baro, Angelika and Laschat, Sabine}
}
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