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Poly(arylene vinylene) Synthesis via a Precursor Step-Growth Polymerization Route Involving the Ramberg–Bäcklund Reaction as a Key Post-Chemical Modification Step

Abstract : The synthesis of conjugated copolymers based on poly(fluorene vinylene) [PFV] and poly(fluorene vinylene-co-carbazole vinylene) [PFVCV] was achieved via a previously unexplored precursor three-step synthetic route involving the Ramberg-Bäcklund reaction. The resulting -conjugated (co)polymers proved highly soluble in common organic solvents, such as DCM, THF, or CHCl3. The solution step-growth polymerization between 2,7-bis(bromomethyl)-9,9'-dihexyl-9H-fluorene [F-Br] and 2,7-bis(mercaptomethyl)-9,9'-dihexyl-9H-fluorene [F-SH] was carried out under basic conditions at 100 °C in a mixture of MeOH and THF. The resulting polysulfides were then subjected to an oxidation reaction using m-CPBA, which was followed by the Ramberg-Bäcklund reaction in the presence of CF2Br2/Al2O3-KOH, thus achieving the desired PFV. Similarly, PFVCV could be synthesized through the same three-step sequence employing, in this case, 2,7-bis(mercaptomethyl)-9-(tridecan-7-yl)-9H-carbazole (C-SH) and F-Br. Conjugated polymers with apparent molecular weights up to 15 kg.mol-1 and exhibiting promising optical features were obtained following this convenient synthetic strategy.
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https://hal.archives-ouvertes.fr/hal-01858135
Contributor : Eric Cloutet <>
Submitted on : Monday, August 20, 2018 - 8:51:05 AM
Last modification on : Tuesday, May 12, 2020 - 11:02:01 AM

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Kunche Aravindu, Eric Cloutet, Cyril Brochon, Georges Hadziioannou, Joan Vignolle, et al.. Poly(arylene vinylene) Synthesis via a Precursor Step-Growth Polymerization Route Involving the Ramberg–Bäcklund Reaction as a Key Post-Chemical Modification Step. Macromolecules, American Chemical Society, 2018, 51 (15), pp.5852 - 5862. ⟨10.1021/acs.macromol.8b00676⟩. ⟨hal-01858135⟩

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