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Design of conjugated materials with side chain azo-linkages
Savita Meena,Josemon Jacob 한국고분자학회 2023 Macromolecular Research Vol.31 No.12
In this paper, we report on the synthesis and characterization of novel conjugated polymers P1–P4 bearing side chain azo-linkages. A diazotization coupling approach was used to design the dibromo functionalized azo-linked target monomers M1–M4 containing one or two azo groups. Monomer 4-((2,5-dibromophenyl)diazenyl)-N,N-dioctylaniline M2 was copolymerized with different donor–acceptor units to obtain polymers P1–P4. Suzuki polymerization reaction was used to synthesize poly[N,N-dioctyl-4-(phenyldiazenyl)aniline-alt-9,9-dioctyl-9H-fluorene] P1 whereas direct arylation polymerization reaction was used to synthesize poly[N,N-dioctyl-4-(phenyldiazenyl)aniline-alt-3-octylthiophene] P2, poly[N,N-dioctyl-4-(phenyldiazenyl)aniline-alt-4,7-bis(4-octylthiophen-2-yl)benzo[c][1,2,5]thiadiazole] P3 and poly[N,N-dioctyl-4-(phenyldiazenyl)aniline-alt-4,4-dioctyl-4H-cyclopenta[1,2-b:5,4-b']dithiophene] P4. Thermogravimetric analyses showed good thermal stability with onset degradation temperatures in the range of 222–338 °C for P1–P4 (T5). All polymers possess good molecular weights with MW ranging from 9.31 to 10.90 kDa. UV–Vis studies on P1–P4 in solution and thin film show their absorption maxima to be between 434 and 517 nm with their optical band gaps falling in the range of 1.94–2.33 eV.