Synthesis of Soluble Polythiophene Partially Containing 3,4-Ethylenedioxythiophene and 3-Hexylthiophene by Polycondensation

Abstract

A novel poly(quinquethiophene) partially containing 3,4-ethylenedioxythiophene (EDOT) and 3-hexylthiophene, poly(3,3''''-dihexyl-3',4',3''',4'''-diethylenedioxy-2,2':5',2'':5'',2''':5''',2''''-quinquethiophene), was synthesized by three types of polycondensations. Among them, direct C-H coupling reaction gave the polymer with the highest molecular weight. The resulting polymer was soluble in common organic solvents. Absorption and fluorescence spectra of the polymer showed a remarkable red-shift compared with the corresponding monomer due to the expansion of effective π-conjugation length.

Transition metal–assisted carbonization of small organic molecules toward functional carbon materials

“…320 nm, while the maximum absorption of DBrBTh/Co-200 generates bathochromic shift to ca. 395 nm, indicating the formation of thiophene oligomers with a bigger conjugated system ( 41 , 42 ).…”

In situ conductivity measurements of polythiophene partially containing 3,4-ethylenedioxythiophene and 3-hexylthiophene

“…A polythiophene partially containing EDOT, polyHE5T, was synthesized by our previous report [25]. PolyHE5T was synthesized by polycondensation reaction between HE5T and dibromo-HE5T (2,5-dibromo-3,3″″-dihexyl-3′,4′,3‴,4‴-diethylenedioxy-2,2′:5′ ,2″ :5″,2‴:5‴,2″″-quinquethiophene) using bis(dibenzylideneacetone)palladium(0) (Pd(dba) 2 ), tris(omethoxyphenyl)phosphine (P(o-MeOPh) 3 ), cesium carbonate, and tetrahydrofuran as a catalyst, ligand, base, and solvent, respectively.…”

“…We investigated several polymerization methods to obtain a neutral polythiophene partially containing EDOT (polyHE5T, Fig. 1b) with both good solubility to organic solvents and high molecular weight [25]. Among them, polycondensation using direct C-H coupling reaction was found to be the best results.…”

Recent developments in the synthesis of regioregular thiophene-based conjugated polymers for electronic and optoelectronic applications using nickel and palladium-based catalytic systems

“…In 2014, Ichiro Imae and coworkers reported the synthesis of poly(quinquethiophene), that is poly(3,3 000 -dihexyl-3,4 0 ,3 000 ,4 000 -diethylenedioxy-2,2 0 :5 0 ,2 00 :5 00 ,2 000 :5 000 ,2 0000 quinquethiophene),partially containing 3-hexylthiophene and 3,4-ethylenedioxythiophene (EDOT), via Suzuki, Stille and DArP protocol. 297 Among them, direct C-H coupling reaction produced the polymer with the highest molecular weight. The polymer was soluble in common organic solvents and a signicant red shi was observed with uorescence and absorption spectra compared to the corresponding monomeric unit due to enhancement of p-conjugation length.…”