Synthesis of Polyphenylenes and Polynaphthalenes by Thermolysis of Enediynes and Dialkynylbenzenes
Abstract
Described are the syntheses of substituted enediynes and dialkynylbenzenes using Pd- or Pd/Cu-catalyzed cross coupling procedures. The products were then thermalized, generally in benzene, to afford the corresponding poly(p-phenylene)s and poly(1,4-naphthalene)s. Thirteen examples are provided that show the scope of the polymerization process based upon substituent patterns and cyclization moieties. The superb thermal resiliency of the newly derived polymers is demonstrated using thermogravimetric analysis. The polymer structure was generally confirmed using IR data correlations to small molecules that resembled the polymer's repeat unit structure. Radical trapping of dimeric intermediates, that were analyzed by GCMS, further substantiated the proposed mechanistic route. The step-growth polymerization pattern was determined by monitoring the degree of monomer consumption versus the polymer molecular weight.
Document Details
- Document Type
- Technical Report
- Publication Date
- Jun 28, 1994
- Accession Number
- ADA281611
Entities
People
- James Tour
- Jens A. John
Organizations
- University of South Carolina