Novel Synthesis of Protected Thiol End-Capped Stilbenes and Oligo(phenylenevinylene)s (OPVs)
The first general procedures for preparation of thiol end-capped stilbenes and oligo(phenylenevinylene)s (OPVs) with tert-butyl- and acetyl-protected thiol termini have been developed. These reactions proceed via Br/Li exchange, McMurry, and Wittig-type reactions. The thiol functionality is protecte...
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Veröffentlicht in: | Journal of organic chemistry 2003-02, Vol.68 (4), p.1275-1282 |
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Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | The first general procedures for preparation of thiol end-capped stilbenes and oligo(phenylenevinylene)s (OPVs) with tert-butyl- and acetyl-protected thiol termini have been developed. These reactions proceed via Br/Li exchange, McMurry, and Wittig-type reactions. The thiol functionality is protected against strong basic and acidic reaction conditions as a t-Bu sulfide. As a key point in the method, reprotection of the thiol group is accomplished by means of acetyl chloride and boron tribromide. The novel strategy forms the basis for stepwise introduction of 4-mercaptostyryl units in OPVs. The new mono-, di-, and trimercapto OPVs have potential applications as one, two, and three terminal molecular devices in gold nanoparticle clusters, self-assembled monolayers, and optoelectronic devices. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/jo0263770 |