Accession Number : ADA296388

Title :   Synthesis and Properties of Low-Bandgap Zwitterionic and Planar Conjugated Pyrrole-Derived Polymeric Sensors. Reversible Optical Absorption Maxima from the UV to the Near-IR.

Descriptive Note : Technical rept.,

Corporate Author : SOUTH CAROLINA UNIV COLUMBIA DEPT OF CHEMISTRY AND BIOCHEMISTRY

Personal Author(s) : Brockmann, Thorsen W. ; Tour, James M.

PDF Url : ADA296388

Report Date : 07 JUN 1995

Pagination or Media Count : 38

Abstract : Described are the polymerizations of three new dibrominated carbonyl-stabilized yield monomers using copper-bronze in DME to afford polymers that are soluble in common solvents and have unique optical and electronic properties. The first monomer is a zwitterionic N- (butyl)pyrrolinium oxide derivative which, upon polymerization, gives a polymer that has a strong optical absorbance at 520 nm in CCl4. An inter-unit ionic interaction is proposed to explain this large red-shifted band. Bronsted bases and Lewis bases induce a reversible structural change in the polymer to give bathochromic shifts from the visible to the near-IR spectral region. Upon mild reduction of the zwitterionic polymer with Pd/C and H2 (1 atm), some of the extended conjugation is lost, but a polymer forms that has an enormous optical absorption maximum range from the near-UV (290 nm) to the near-IR (886 nm) depending on the solvent or hydroxide concentration. A sample of the reduced polymer can be dispersed in plasticized poly(vinyl chloride). The flexible polymer composite reversibly changes from dark blue-brown in aqueous sodium hydroxide to bright yellow-orange in aqueous HCl. The second monomer, a zwitterionic N-(dodecyl)pyrrolinium oxide derivative, was also synthesized in three steps from pyrrole, and upon polymerization, gives rise to a polymer which also responds reversibly towards Bronsted and Lewis bases. This polymer can be solution cast into flexible-free standing films. jg p.2

Descriptors :   *ULTRAVIOLET RADIATION, *POLYMERS, *PYRROLES, *NEAR INFRARED RADIATION, ELECTRONICS, OPTICAL PROPERTIES, DETECTORS, SOLUTIONS(MIXTURES), SYNTHESIS, MODIFICATION, STRUCTURAL PROPERTIES, ELECTROMAGNETIC PROPERTIES, POLYMERIZATION, FILMS, HYDROGEN, REDUCTION, SPECTRA, OXIDES, RADIATION ABSORPTION, COPPER, REVERSIBLE, CHLORIDES, MONOMERS, SOLVENTS, ABSORPTION, PALLADIUM, HYDROXIDES, BROMINE, CARBONYL COMPOUNDS, IONIC CURRENT, VINYL RADICALS, BASES(CHEMISTRY), POLYVINYL CHLORIDE, PLASTICIZERS, SODIUM HYDROXIDE, BRONZE, CARBON TETRACHLORIDE.

Subject Categories : Polymer Chemistry
      Organic Chemistry
      Physical Chemistry
      Atomic and Molecular Physics and Spectroscopy
      Optics

Distribution Statement : APPROVED FOR PUBLIC RELEASE