Synthesis and Characterization of End-Functionalized Poly(3-butylthiophene) with Semifluoroalkyl Chains

A new poly(3-butylthiophene) derivative with one terminus functionalized with a 1H,1H,2H,2H,3H,3H-perfluoroundecyl group (P3BT-F17) is synthesized by Ni-catalyzed quasi-living polymerization and the subsequent quenching of living ends by allyl-Grignard reagent and the attachment of a fluoroalkyl chain. The quantitative introduction of fluoroalkyl chain ends is confirmed by matrix-assisted laser desorption/ionization time-of-flight-mass spectrometry (MALDI-TOF-MS), gel-permeation chromatography (GPC), 1H NMR spectroscopy, and X-ray photoelectron spectroscopy (XPS). The electronic properties of P3BT-F17 in solution and its crystalline structure in the solid state are investigated by UV-vis spectroscopy and cyclic voltammetry (CV), and by DSC and X-ray diffraction (XRD) analyses.