Accession Number : ADA296062

Title :   Imine Bridged Planar Poly(p-phenylene) Derivatives for Maximization of Extended p-Conjugation. The Common Intermediate Approach.

Descriptive Note : Technical rept.,

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

Personal Author(s) : Lamba, Jaydeep J. ; Tour, James M.

PDF Url : ADA296062

Report Date : 07 JUN 1995

Pagination or Media Count : 57

Abstract : Described are two approaches to planar conjugated poly(p-phenylene) (PPP) derivatives. The first approach, involving lactam bridges, was unsuccessful due to the insolubility of the 6(511)-phenanthridinonyl moieties. The second approach, which utilized imine bridges, worked excellently since the compounds were generally soluble and the bridge formations were highly efficient. The main PPP backbone was synthesized via Pd(O)-catalyzed coupling of an arylbis(boronic ester) with an aryldibromide. Imine bridges, that are formed by exposure of the polymer to trifluoroacetic acid or HCl, force the consecutive units into planarity. The bridging units are sp2 hybridized thus allowing for greater it-electron flow between the consecutive phenyl units. The polymers, upon planarization, exhibit enormous bathochromic shifts of 210-240 nm.

Descriptors :   *PLANAR STRUCTURES, *IMINES, POLYMERS, FILMS, VISIBLE SPECTRA, CATALYSTS, ALKYLATION, SOLUBILITY, PHENOLS, BRIDGES, FLEXIBLE MATERIALS, KETONES.

Subject Categories : Organic Chemistry
      Electrical and Electronic Equipment

Distribution Statement : APPROVED FOR PUBLIC RELEASE