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Building Blocks for Thiacrown Ether Compounds

3,7-Dithia-1,9-nonanedithiol (1) and 3,7-Dithia-1,9-nonanediol (2) can be utilized in the synthesis of sulfur-containing macrocycles. In this example, macrocycle 3, whose structure is a combination of a thiacrown ether and 1,10-phenanthroline, is synthesized from 1 and a 1,10-phenanthroline derivative. The nickel(II) complex of 3 was developed as a new model compound for metalloenzymes, based on its redox activity.1)

Macrocycle 4, whose structure is a combination of a thiacrown ether and TTF, is synthesized from reagent 2. The thiacrown ether moieties of 4 can complex transition metal cations which then alter the electrochemical properties of the TTF moiety. Metal cation complexes of 4 are being developed as new charge transfer compounds.2)

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