A new cyclic telluride. Synthesis and reactions of 1,3,5,6,7,8‐hexahydronaphtho[2,3‐c]tellurophene

Abstract

Reaction of 6,7‐bis(chloromethyl)‐1,2,3,4‐tetrahydronaphthalene with tellurium powder and potassium iodide in 2‐butoxyethanol gave 2,2‐diiodo‐1,3,5,6,7,8‐hexahydro‐naphtho[2,3‐c]tellurophene(1) as a red‐orange solid in 40% yield. Reduction of 1 with hydrazine hydrate gave a pale yellow solid of 1,3,5,6,7,8‐hexahydronaphtho[2,3‐c]telluro‐phene(2) in 80% yield. Chlorination, bromination of 2 and its reaction with benzyl bromide and N‐bromosuccinimide were reported. 2,2‐Bis(dimethyldithiocarbamato)‐, 2,2‐bis (diethyldithiocarbamato)‐ and 2,2‐bis(piperidine‐1‐carbodithioate)‐1,3,5,6,7,8‐hexahydro‐naphtho[2,3‐c]tellurophene were prepared by the reaction of the corresponding sodium dithiocarbamate salt with 1. Mononuclear platinum complex (ie, [(C12H14Te)2PtCl2]) was obtained by the reaction of 2 with K2PtCl4. Reaction of 6,7‐bis(chloromethyl)‐1,2,3,4‐tetrahydronaphthalene with KTeCN in DMSO solution gave 2,2‐dihydroxo‐1,3,5,6,7,8‐hexahydronaphtho[2,3‐c]tellurophene (11) as a white solid in 55% yield. All these new compounds were characterized by elemental analysis, IR, 1H, and 13C NMR, and mass spectroscopic data.

Synthesis and self-assembly of thiol-modified tellurophenes

“…Therefore, the ongoing exploration of these unique metalloid-containing heterocycles, including their synthesis and polymerization, is important. [37][38][39][40][41][42][43][44][45][46][47] Additionally, thiophene and polythiophene derivatives have been directly conjugated to metal surfaces through thiosulfate and thiol linkers, 48 demonstrating the interest in chalcogenophenes for these materials. Given the unique chemistry and potential applications of both small molecule and polymeric tellurophenes, and considering that tellurophene derivatives have been shown to function as sensors of oxygen and multidentate anionic species, 49,50 developing a route to a solid-state detection system expands the environments in which a tellurophene-based sensor can be used.…”