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Organic Metals and Superconductors: Facile Synthetic Methodologies Bypassing Coupling and Chromatography

Published online by Cambridge University Press:  10 February 2011

Ronald L. Meline  and
Ronald L. Elsenbaumer
Ronald L. Meline
Affiliation:
Department of Chemistry and Biochemistry, The University of Texas at Arlington Arlington, TX 76019([email protected])
Ronald L. Elsenbaumer
Affiliation:
Department of Chemistry and Biochemistry, The University of Texas at Arlington Arlington, TX 76019([email protected])
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Abstract

The organic donor tetrathiafulvalene (TTF, 1) and its derivatives are synthesized from tetrathianaphthalene (TTN, 2) in a one pot reaction. The reaction takes advantage of an isomerization of lithiated TTN into lithiated TTF and subsequent substitution with novel disulfide electrophiles yielding substituted T donors. The isomerization approach eliminates the need for a chemical coupling reaction of oxones or thiones (a yield limiting procedure), and simple byproducts eliminate the need for tedious purification. The novel methodology allows for a high yield preparation of bis(ethylenedithio)tetrathiafulvalene (BEDT-TTF, 3a, 80%) and bis(propylenedithio)tetrathiafulvalene (BPDT-TTF, 3b), previously unavailable directly from TTF. A high yield of bis(phenylenedithio)tetrathiafulvalene (BPhDT-TTF, 3c, unavailable from dimercaptoisotrithione “DMIT”) is also achieved using the synthetic scheme. The method is general, and can be used to prepare a variety of novel organic donors based on TTF. Synthetic procedures along with all relevant characterization are presented.

Type
Research Article
Information
MRS Online Proceedings Library (OPL) , Volume 488: Symposium J – Electrical, Optical & Magnetic Properties of Organic IV , 1997 , 659
Copyright
Copyright © Materials Research Society 1998

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