Carbon-rich molecules: synthesis and isolation of aryl/heteroaryl terminal bis(butadiynes) (HC[triple bond]C-C[triple bond]C-Ar-C[triple bond]C-C[triple bond]CH) and their applications in the synthesis of oligo(arylenebutadiynylene) molecular wires

Kara West; Changsheng Wang; Andrei S Batsanov; Martin R Bryce

doi:10.1039/b802968g

Carbon-rich molecules: synthesis and isolation of aryl/heteroaryl terminal bis(butadiynes) (HC[triple bond]C-C[triple bond]C-Ar-C[triple bond]C-C[triple bond]CH) and their applications in the synthesis of oligo(arylenebutadiynylene) molecular wires

Org Biomol Chem. 2008 Jun 7;6(11):1934-7. doi: 10.1039/b802968g. Epub 2008 Apr 8.

Authors

Kara West¹, Changsheng Wang, Andrei S Batsanov, Martin R Bryce

Affiliation

¹ Department of Chemistry, Durham University, Durham, UK.

PMID: 18480906
DOI: 10.1039/b802968g

Abstract

The synthesis, isolation and characterisation are reported for a series of terminal aryl/heteroaryl bis(butadiynes) (HC[triple bond]C-C[triple bond]C-Ar-C[triple bond]C-C[triple bond]CH) 4a-e including the X-ray molecular structure of the 2,5-pyridylene derivative 4d; compound 4a and the mono-protected analogue [HC[triple bond]C-C[triple bond]C-Ar-C[triple bond]C-C[triple bond]C-C(OH)Me2] 5a serve as convenient precursors for the synthesis of highly-conjugated oligo(arylenebutadiynylene)s.