Tetraselenofulvalene, dithiodiselenofulvalene and the TCNQ salts

Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal

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Other Related Categories

260327M, 260327R, C07D42104

Type

Patent

Status

active

Patent number

040283461

Description

ABSTRACT:
Organic molecules can be coupled via their selenocarbonyl derivatives. Generally, the synthesis can be described by the following reaction equation: ##STR1## where C can be a cyclic or heterocyclic organic compound and R can be alkoxy, phenoxy or phenyl, preferably CH.sub.3 O, C.sub.2 H.sub.5 O, C.sub.6 H.sub.5 O, C.sub.6 H.sub.5 and the like. The reaction is usually carried out in a refluxing solvent, the choice of the solvent being determined by the stability and by the ease of coupling of a particular substrate. Groups that tend to stabilize the selenocarbonyl require higher boiling solvents and longer refluxing times. Aromatic solvents, such as benzene or toluene are well-suited for the coupling reaction. In some cases, refluxing the substrate in the alkoxy-phosphorus base as solvent may be advantageous. This new coupling procedure permits the synthesis of the hitherto unknown compounds: tetraselenofulvalene (TSeF), the selenium analogue of tetrathiofulvalene (TTF), and diselenodithiofulvalene (DSeDTF). Highly conducting charge transfer salts of tetraselenofulvalene and diselenodithiofulvalene with tetracyano-p-quinodimethane have also been prepared. The materials of this invention are useful in the organic electronic devices described in copending application Ser. no. 450,541 to Arieh Aviram et al. and assigned to the same assignee as is the present application.

REFERENCES:
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Wudl et al., J. Am. Chem. Soc., vol. 94, pp. 670 and 671 (1972).
Corey et al., JACS, vol. 87, 1965, pp. 934 and 935.
Hartzler JACS, vol. 95, 1973, pp. 4379 and 4385.
Bechgaard et al. "J.C.S. Chem. Comm.", 1974, pp. 937 and 938.
Wudl et al. J.C.S. Chem. Comm. 1970, pp. 1453 and 1454.
Challenger et al., J. Chem. Soc. (1953). pp. 292-304.
Goodings, "Endeavour," 34, pp. 123-130 (1975).
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