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Synthesis and Characterization of End‐Functionalized Poly(3‐butylthiophene) with Semifluoroalkyl Chains
Authors:Jusha Ma  Yanfang Geng  Kazuhito Hashimoto  Keisuke Tajima
Affiliation:1. School of Material Science and Engineering, Beijing Institute of Technology, 5 South Zhongguancun Street, Beijing 100081, China;2. Department of Applied Chemistry, School of Engineering, The University of Tokyo, 7‐3‐1 Hongo, Bunkyo‐ku, Tokyo 113‐8656, Japan;3. Japan Science and Technology Agency (JST), Precursory Research for Embryonic Science and Technology (PRESTO), 4‐1‐8 Honcho, Kawaguchi, Saitama 332‐0012, Japan, RIKEN Center for Emergent Matter Science (CEMS), 2‐1 Hirosawa, Wako, Saitama 351‐0198, Japan
Abstract: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.
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Keywords:conjugated polymers  end‐functionalization  matrix‐assisted laser desorption/ionization time‐of‐light‐mass spectrometry (MALDI‐TOF‐MS)  surfactants
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