Carbodithioate-terminated oligo(phenyleneethynylene)s: synthesis and surface functionalization of gold nanoparticles

Tae-Hong Park; Michael J Therien

doi:10.1021/ol070789j

Carbodithioate-terminated oligo(phenyleneethynylene)s: synthesis and surface functionalization of gold nanoparticles

Org Lett. 2007 Jul 19;9(15):2779-82. doi: 10.1021/ol070789j. Epub 2007 Jun 29.

Authors

Tae-Hong Park¹, Michael J Therien

Affiliation

¹ Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA.

PMID: 17602486
DOI: 10.1021/ol070789j

Abstract

Carbodithioate-terminated bis(phenylene)ethynylenes and oligo(phenyleneethynylene)s have been synthesized from TMSE-protected 4-iododithiobenzoic acid ester (1) and 4-ethynyldithiobenzoic acid ester (3) via Pd-catalyzed cross-coupling reactions. TEM and spectroscopic studies demonstrate that the reaction of 4-(phenylethynyl)dithiobenzoate with alkylamine-protected gold nanoparticles (AuNPs) produces the corresponding organocarbodithioate-functionalized AuNPs.