Efficient solid-phase synthesis of regioregular head-to-tail-coupled oligo(3-alkylthiophene)s up to a dodecamer

Citation
T. Kirschbaum et al., Efficient solid-phase synthesis of regioregular head-to-tail-coupled oligo(3-alkylthiophene)s up to a dodecamer, J CHEM S P1, 8, 2000, pp. 1211-1216
Citations number
30
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Volume
8
Year of publication
2000
Pages
1211 - 1216
Database
ISI
SICI code
0300-922X(2000)8:<1211:ESSORH>2.0.ZU;2-H
Abstract
Solid-phase synthesis of isomerically pure head-to-tail-coupled (HT) oligo( 3-hexylthiophene)s on chloromethylated polystyrene resin has been developed . Using novel sequences of iodination and Suzuki cross-coupling reaction, a series up to a dodecamer has been synthesized in high yield and purity. Re moval of the conjugated oligomers from solid support as methyl esters, sapo nification and decarboxylation to the HT-coupled oligo(3-alkylthiophene)s c ould be effectively achieved.