10.1021/jo001620l
The research focuses on the synthesis of new functionalized derivatives of 3,4-alkylenedioxypyrroles, specifically 3,4-ethylenedioxypyrrole (EDOP) and 3,4-(1,3-propylenedioxy)pyrrole (ProDOP), which are electron-rich monomers used to create highly electroactive and stable conducting polymers for various applications. The study involves N-alkylations of ProDOP to yield derivatives with different pendant chains, such as alkyl, sulfonatoalkoxy, glyme, and glyme alcohol. Iodization of EDOP and ProDOP through iodo-decarboxylation is also explored to obtain iodo-functionalized derivatives for aryl coupling chemistry. Additionally, N-protection and formylation of EDOP are conducted, followed by Knoevenagel condensation to synthesize cyanovinylene-linked diheterocycle monomers. The research also includes the synthesis of a 14-crown-4-ether based dioxypyrrole for potential lithium ion coordination and sensing in electroactive polymers, and C-alkylation of ProDOPs to create soluble π-conjugated polymers. The experiments utilize various reactants, including sodium hydride, alkylating reagents, and different protecting groups, and employ techniques like column chromatography, rotary evaporation, and acid-base titration for purification and isolation of products. Analytical methods such as 1H and 13C NMR, FT-IR, HRMS, and elemental analysis are used to characterize the synthesized compounds.
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