Facile Syntheses of 4-(2-Cyanoethylthio)-1,3-dithiole-2-thione and New Electron­ Donors with Two TTF Units and Compounds with Bis(1,3-dithiole-2-thione) Groups

Abstract

The synthetic conditions for the preparation of 4-(2-cyanoethylthio)-1,3-dithiole-2-thione (1) from TBA 2 ×[Zn(dmit) 2 ] were studied. Compound 1 was used to synthesize new electron donors with two tetrathiafulvalene (TTF) units. Other interesting compounds that are good precursors for tetrathiafulvalenophanes were also easily prepared from TBA 2 ×[Zn(dmit) 2 ].

Tetrathiafulvalene and π-extended tetrathiafulvalene pillar[5]arene conjugates: synthesis, electrochemistry and host–guest properties

“…TTF-based compounds 3a–b were synthesized starting from pillar[5]arene 1 36 and the cyanoethylthio-protected TTF derivatives 2a–b . The thiolate intermediates derived from 2a 37 and 2b 38 were generated in situ by treatment with caesium hydroxide in MeOH/ N , N -dimethylformamide (DMF). Subsequent reaction with decabromide 1 at 45 °C then afforded compounds 3a and 3b with excellent yields (91%), having in mind that ten covalent bonds are created in a single step.…”

“…Analytical data is identical to the one previously reported in the literature. 37 Compound 2b. A solution of cesium hydroxide monohydrate (262 mg, 1.56 mmol) in absolute methanol (3.5 mL) was added to a solution of 2,3-bis(2-cyanoethylsulfanyl-6,7-bis(methylsulfanyl) tetrathiafulvalene (694.5 mg, 1.488 mmol) in DMF (20 mL).…”

A triad molecular conductor: simultaneous control of charge and molecular arrangements

“…Synthesis of the new triad molecule ( 1 ) is demonstrated in Scheme 1. A TTF derivative 2 17 was reacted with NaOMe in THF at room temperature, followed by treatment with chloroiodomethane to afford compound 3 in a 96% yield. Reaction of 3 with excess NaI converted the chloromethylthio group to an iodomethylthio group, providing 4 in a 96% yield.…”