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Preparation of Synthetic Precursors to Tetrathiafulvalene Derivatives

IP.com Disclosure Number: IPCOM000084141D
Original Publication Date: 1975-Sep-01
Included in the Prior Art Database: 2005-Mar-02
Document File: 4 page(s) / 86K

Publishing Venue

IBM

Related People

Engler, EM: AUTHOR [+2]

Abstract

The substitution of selenium for sulfur in the organic donor, tetrathiafulvalene (TTF,1) to yield tetraselenafulvalene (TSeF, 2), has led to an improvement of the metallic properties of the highly conducting charge transfer salt, TTF-TCNQ. (Image Omitted)

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Preparation of Synthetic Precursors to Tetrathiafulvalene Derivatives

The substitution of selenium for sulfur in the organic donor, tetrathiafulvalene (TTF,1) to yield tetraselenafulvalene (TSeF, 2), has led to an improvement of the metallic properties of the highly conducting charge transfer salt, TTF-TCNQ.

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Existing synthetic procedures cannot be employed to prepare TSeF or any other similar derivative containing selenium (such as cis/trans DSeDTF (4 and 5) and substituted analogues of 2, 4 and 5). Therefore, a new synthetic procedure, involving the coupling of molecular units possessing a selenocarbonyl (C=Se)

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by deselenization using an alkyl phosphite base, has been developed. The presence of the selenocarbonyl (C=Se) is crucial to the success of the coupling reaction. Table I demonstrates this point.

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Reactions 1, 2 and 3, which involve coupling of a selenocarbonyl, proceed under relatively mild conditions in good yields to give the corresponding TTF derivatives. The analogous coupling reactions 4 and 5 in Table I, however, involve desulfurization of a thiocarbonyl (C=S) which reacts much more sluggishly, requiring considerably more vigorous conditions, and yields only trace amounts of the desired product.

These examples demonstrate the importance of the selenocarbonyl bond for the success of this synthetic procedure. Unfortunately, most syntheses of the vinylene carbonate precursors lead to a thi...