Synthesis of glucose-substituted poly(<Emphasis Type="Italic">p</Emphasis>-phenylene)s with twisted main-chain in one direction due to induced axial chirality

Summary The peracetylated and free glucose-substituted poly(p-phenylene)s were synthesized by the coupling polymerization of a dibromobenzene monomer using Ni complex and the subsequent deacetylation by hydrazine monohydrate. The polymerization was carried out using bis(1,5-cyclooctadiene)nickel(0) (Ni(COD)₂) as a coupling agent with 2,2’-bipyridyl (bpy) and 1,5-cyclooctadiene (COD) in a mixed solvent of DMF and toluene. The structure of the product was confirmed by ¹H and ¹³C NMR measurements to be the poly(p-phenylene) having peracetylated glucose residues. The M_n values were estimated by GPC analysis with DMF as eluent to be 7300–9800. The fluorescence analysis of the polymer was carried out in comparison with that of the dimeric model compound. The CD spectrum of the polymer indicated that the main-chain was twisted and immobilized in one direction due to the chirality and bulkily of the peracetylated glucose residues. The deacetylation using hydrazine monohydrate completely took place to give the free glucose-substituted poly(p-phenylene).