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BIS(1,3 Dithiole) Compounds

IP.com Disclosure Number: IPCOM000089817D
Original Publication Date: 1977-Dec-01
Included in the Prior Art Database: 2005-Mar-05
Document File: 2 page(s) / 34K

Publishing Venue

IBM

Related People

Andersen, JR: AUTHOR [+4]

Abstract

There is described the preparation of bis-1,3-dithiole compounds (I) which are key synthetic precursors for the preparation of new polymeric metal bis(dithiolene) (i.e., II) and tetrathiafulvalene compounds (i.e., III): (Image Omitted)

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BIS(1,3 Dithiole) Compounds

There is described the preparation of bis-1,3-dithiole compounds (I) which are key synthetic precursors for the preparation of new polymeric metal bis(dithiolene) (i.e., II) and tetrathiafulvalene compounds (i.e., III):

(Image Omitted)

There has been increasing interest in preparing polymeric analogs of tetrathiafulvalene and metal bis(dithiolene) because of their potentially useful electrical and optical properties.

Compounds of the type 1 have been prepared by reacting 1, 4-dibromo-2,3- butadione with an N,N-dialkyl carbonate or an 0-alkyl xanthate, followed by acid catalyized cyclization, to give compounds IV and V, respectively. The procedure used has also been extended to the selenium analogs (compound VI). The reactions involved are shown below:

(Image Omitted)

Compound IV was prepared as the dimethyl (R=R'=CH(3)), methyl isopropyl (R=CH(3), R'=i-C(3)H(7)) and piperdinyl (R=R'=(CH(2))(5)) derivatives and with the assigned structures. The bis(2-dialkyliminium-1,3-dithiole) derivatives react with alkali TCNQ salts to give semiconducting charge-transfer complexes. Compound VI was prepared with R/R'=(CH(2))(5). These reactions proceed in good yields. Compounds IV and VI can be converted to derivatives suitable for self-coupling, such as shown below:

(Image Omitted)

Further, compounds VII and VIII can be cross-coupled with 1,3-dithiole or 1,3-diselenole derivatives to yield a variety of bis(TTF) and bis-(TSeF) derivatives which should...