Macromolecules featuring distinct aromatic segments are being investigated for use in organic electronic materials. Acyclic Diene metathesis (ADMET) has been used in a unique way to access segmented conjugated polymers containing electro-optically active aromatic segments. In the past, we reported ADMET as a convenient route to yield various macromolecular architectures containing homologous electro-optically active conjugated aromatic segments on the either side of the heteroatom. We report here the further extension of ADMET strategy to build various conjugated polymers featuring alternating distinct fluorophores. Structure/property relationships are investigated, specifically electronic interactions between the aromatic conjugated segments and their influence on the electro-optical material characteristics. In the first step, divinyl monomers based on thiophene and phenylenes, bearing solubilizing side chains have been synthesized. In the subsequent step, the monomers are efficiently polymerized via Acyclic Diene Metathesis (ADMET) to afford segmented conjugated polymers. We are currently applying the synthetic approach to build donor and acceptor based conjugated polymers which are of special interest as materials for organic photovoltaics. Polymers are exclusively trans-configured at the internal vinylene bonds. The structures were confirmed by 1H, 13C, HSQC and HBMC NMR analysis. The polymers are highly fluorescent with the fluorescence quantum efficiencies in the range of 0.40-0.60 The GPC number average molecular weight of the polymers was found out to be in the range of 3200-5600 g/mol. 

Design and synthesis of segmented conjugated polymers via acyclic diene metathesis (ADMET)

248th National Meeting (2014)

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