Pentafluorobenzene end-group as a versatile handle for para fluoro “click” functionalization of polythiophenes† †Electronic supplementary information (ESI) available: Experimental details, MALDI-TOF, 1H and 19F NMR, UV-visible spectroscopy, and photoluminescence spectroscopy results. See DOI: 10.1039/c6sc04427a Click here for additional data file.

نویسندگان

  • Pierre Boufflet
  • Abby Casey
  • Yiren Xia
  • Paul N. Stavrinou
  • Martin Heeney
چکیده

A convenient method of introducing pentafluorobenzene (PFB) as a single end-group in polythiophene derivatives is reported via in situ quenching of the polymerization. We demonstrate that the PFB-group is a particularly useful end-group due to its ability to undergo fast nucleophilic aromatic substitutions. Using this molecular handle, we are able to quantitatively tether a variety of common nucleophiles to the polythiophene backbone. The mild conditions required for the reaction allows sensitive functional moieties, such as biotin or a cross-linkable trimethoxysilane, to be introduced as end-groups. The high yield enabled the formation of a diblock rod-coil polymer from equimolar reactants under transition metal-free conditions at room temperature. We further demonstrate that water soluble polythiophenes end-capped with PFB can be prepared via the hydrolysis of an ester precursor, and that such polymers are amenable to functionalization under aqueous conditions.

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منابع مشابه

π-extended [12]cycloparaphenylenes: from a hexaphenylbenzene cyclohexamer to its unexpected C 2-symmetric congener† †Electronic supplementary information (ESI) available: Experimental protocols, crystallographic data for 3 and 5, 1H NMR, 13C NMR, 2D NMR, MALDI-TOF MS, as well as computational details. CCDC 1033267 1033268. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc02547h Click here for additional data file. Click here for additional data file.

Florian E. Golling†,‡, Silvio Osella§, Martin Quernheim†, Manfred Wagner†, David Beljonne§, Klaus Müllen†,* † Max-Planck-Institut für Polymerforschung, Ackermannweg 10, 55128 Mainz (Germany) ‡ Graduate School Materials Science in Mainz, Staudinger Weg 9, 55128 Mainz (Germany) § Chimie des Matériaux Nouveaux & Centre d'Innovation et de Recherche en Matériaux Polymères, Université de MonsUMONS/Ma...

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Department of Chemistry, Graduate Schoo Kyoto 606-8502, Japan. E-mail: osuka@kuc Spectroscopy Laboratory for Functional p Chemistry Yonsei University, Seoul 120-749 † Electronic supplementary information methods, HR-ESI-TOF mass spectra, UV cyclic voltammograms, X-ray crystal struc CCDC 1025770, 1025771 and 1025772. Fo or other electronic format see DOI: 10.103 Cite this: Chem. Sci., 2015, 6, 1696

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Pentafluorobenzene end-group as a versatile handle for para fluoro "click" functionalization of polythiophenes.

A convenient method of introducing pentafluorobenzene (PFB) as a single end-group in polythiophene derivatives is reported via in situ quenching of the polymerization. We demonstrate that the PFB-group is a particularly useful end-group due to its ability to undergo fast nucleophilic aromatic substitutions. Using this molecular handle, we are able to quantitatively tether a variety of common nu...

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عنوان ژورنال:

دوره 8  شماره 

صفحات  -

تاریخ انتشار 2017