This presentation will cover recent advances from our lab in regards to the synthesis of conjugated polymers based on a cyclopenta-fused polycyclic aromatic hydrocarbons (CP-PAHs). The method of polymerization described here involves a palladium-catalysed cyclopentannulation between 9,10-dibromoanthracene and bis-ethynylene containing monomers. The bis-ethynylene monomer composition was systematically varied in structure via the utilization of a series of substituted aryl or thiophene ring systems. After obtaining a preliminary polymer via the step-growth polymerization, the polymers were subjected to a Scholl cyclodehydrogenation reaction to access a rigid, fully conjugated ladder polymer (Figure 1). The polymers obtained after Scholl cyclodehydrogenation were considerably less soluble than the precursor polymers, gave higher apparent molecular weights via gel permeation chromatography, and showed a bathochromic shift in the absorption spectra. The polymers optoelectronic properties were modulated depending on the aryl substitutions with some polymer systems reaching optical band gaps as low as 1.2 eV. This poster will cover the synthetic methodology to access these materials as well as provide the materials characterization results.

Cyclopenta-fused, polycyclic, aromatic hydrocarbon-based conjugated polymers

251st National Meeting (2016)

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