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Title: Installation of a reactive site for covalent wiring onto an intrinsically conductive poly(ionic liquid)

We describe post-polymerization radical bromination of a nanostructured poly(ionic liquid) that selectively introduces a reactive bromo-group onto the polyalkylthiophene backbone. Raman and FT-IR spectroscopy proves that the bromine is successfully introduced at the 3-methyl position of the thiophene and that the molecular structure of the polymer remains largely intact with only minimal chain scission detected. FT-IR and Vis-NIR spectroscopy indicates that incorporation of the bromine induces twisting (loss of co-planarity) of the polythiophene backbone. WAXS confirms retention of an ordered lamellar structure with minor lattice spacing contraction. Cyclic voltammetry confirms spectroscopic findings that the bromination reaction yields a stable p-doped polymer. The installed bromine is susceptible to nucleophilic displacement permitting the covalent attachment of other functional molecules, such as a dialkylphosphonate. Elemental analysis of such a transformation established that 100 % functionalization can be achieved. These results collectively demonstrate that post-modification of a π-conjugated polymer can be used to both tune electronic and photonic properties, as well as install a chemoselective attachment point for the covalent wiring of other molecules.
Authors:
 [1] ;  [1] ;  [2]
  1. Argonne National Lab. (ANL), Argonne, IL (United States)
  2. Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
Publication Date:
OSTI Identifier:
1240395
Report Number(s):
LA-UR--14-28733
Journal ID: ISSN 1381-5148; PII: S1381514814002193
Grant/Contract Number:
AC52-06NA25396; AC04-94AL85000
Type:
Accepted Manuscript
Journal Name:
Reactive and Functional Polymers
Additional Journal Information:
Journal Volume: 85; Journal ID: ISSN 1381-5148
Publisher:
Elsevier
Research Org:
Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)
Sponsoring Org:
USDOE
Country of Publication:
United States
Language:
English
Subject:
77 NANOSCIENCE AND NANOTECHNOLOGY Functional interfaces; post-polymerization radical bromination; poly(ionic liquid); dual conductive polymers