Studies on 3-(2-Ethylhexyl)thiophene Polymers

Synthesis, structures, and density functional theory computational study of thiophene‐containing and fluorodecorated imine‐linked polymers

“…The total energies of the four polymer building blocks resulting from the DFT calculations revealed that their stabilities were in the following order: P(T3–IPI) > P(T2FB–IPI) > P(P2T–IPI) > P(P2FB–IPI), as summarized in Table . One of the main factors that might have controlled this stability trend was the number of thiophene rings in the polymer chain . The higher the number of thiophene rings in the polymer chain was, the lower E T was, and hence, the higher the stability of the polymer was.…”

“…One of the main factors that might have controlled this stability trend was the number of thiophene rings in the polymer chain. 38 The higher the number of thiophene rings in the polymer chain was, the lower E T was, and hence, the higher the stability of the polymer was. This was attributed to the better conjugation provided by the thiophene rings.…”

Synthesis, structures, and density functional theory computational study of thiophene‐containing and fluorodecorated imine‐linked polymers

“…The total energies of the four polymer building blocks resulting from the DFT calculations revealed that their stabilities were in the following order: P(T3–IPI) > P(T2FB–IPI) > P(P2T–IPI) > P(P2FB–IPI), as summarized in Table . One of the main factors that might have controlled this stability trend was the number of thiophene rings in the polymer chain . The higher the number of thiophene rings in the polymer chain was, the lower E T was, and hence, the higher the stability of the polymer was.…”

“…One of the main factors that might have controlled this stability trend was the number of thiophene rings in the polymer chain. 38 The higher the number of thiophene rings in the polymer chain was, the lower E T was, and hence, the higher the stability of the polymer was. This was attributed to the better conjugation provided by the thiophene rings.…”

Poly(3-hexylthiophene) Based Block Copolymers Prepared by “Click” Chemistry

“…Alkynyl-terminated regioregular P3HTs were synthesized by the Grignard metathesis (GRIM) as shown in Scheme 2 and according to methods detailed in the literature. 15,29,30 2,5-Dibromo-3-hexylthiophene (7), that had been prepared in two steps following published procedures, 31,32 was reacted with tertbutylmagnesium chloride to yield 2-bromo-5-magnesiochloro-3-hexylthiophene as a major product. 33 The addition of Ni(dppp)Cl 2 to the reaction mixture resulted in the formation of "living" P3HT effectively end-capped by a highly active Ni 0 group.…”

Extremely regio‐regular poly (3‐alkylthiophene)s from simplified chain‐growth Grignard metathesis polymerisations and the modification of their chain‐ends

“…3‐Bromothiophene, n‐butyl bromide, n ‐hexyl bromide, Ni(dppp)Cl 2 , N ‐bromosuccinimide (NBS), isopropylmagnesium chloride (iPMgCl, 2 M in THF), methyl magnesium bromide (3 M in THF), LiAlH 4 , N ‐methylformanilide, trifluoromethanesulfonic anhydride (TFMSA), 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DCBQ), triphenyl phosphine, and tetra‐n‐butylammonium bromide of standard grade (Aldrich, France) were used as received unless otherwise noted. The synthesis of the monomers, 2,5‐dibromo‐3‐butylthiophene and 2,5‐dibromo‐3‐hexylthiophene, from the bromination of 3‐butylthiophene and 3‐hexylthiophene, respectively, was carried out via a route similar to that described elsewhere 44, 45. A representative preparation of the butylated monomer is given below for the sake of completeness.…”

Synthesis, structures, and density functional theory computational study of thiophene‐containing and fluorodecorated imine‐linked polymers

“…The total energies of the four polymer building blocks resulting from the DFT calculations revealed that their stabilities were in the following order: P(T3–IPI) > P(T2FB–IPI) > P(P2T–IPI) > P(P2FB–IPI), as summarized in Table . One of the main factors that might have controlled this stability trend was the number of thiophene rings in the polymer chain . The higher the number of thiophene rings in the polymer chain was, the lower E T was, and hence, the higher the stability of the polymer was.…”

“…One of the main factors that might have controlled this stability trend was the number of thiophene rings in the polymer chain. 38 The higher the number of thiophene rings in the polymer chain was, the lower E T was, and hence, the higher the stability of the polymer was. This was attributed to the better conjugation provided by the thiophene rings.…”

Poly(3-hexylthiophene) Based Block Copolymers Prepared by “Click” Chemistry

“…Alkynyl-terminated regioregular P3HTs were synthesized by the Grignard metathesis (GRIM) as shown in Scheme 2 and according to methods detailed in the literature. 15,29,30 2,5-Dibromo-3-hexylthiophene (7), that had been prepared in two steps following published procedures, 31,32 was reacted with tertbutylmagnesium chloride to yield 2-bromo-5-magnesiochloro-3-hexylthiophene as a major product. 33 The addition of Ni(dppp)Cl 2 to the reaction mixture resulted in the formation of "living" P3HT effectively end-capped by a highly active Ni 0 group.…”

Extremely regio‐regular poly (3‐alkylthiophene)s from simplified chain‐growth Grignard metathesis polymerisations and the modification of their chain‐ends

“…3‐Bromothiophene, n‐butyl bromide, n ‐hexyl bromide, Ni(dppp)Cl 2 , N ‐bromosuccinimide (NBS), isopropylmagnesium chloride (iPMgCl, 2 M in THF), methyl magnesium bromide (3 M in THF), LiAlH 4 , N ‐methylformanilide, trifluoromethanesulfonic anhydride (TFMSA), 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DCBQ), triphenyl phosphine, and tetra‐n‐butylammonium bromide of standard grade (Aldrich, France) were used as received unless otherwise noted. The synthesis of the monomers, 2,5‐dibromo‐3‐butylthiophene and 2,5‐dibromo‐3‐hexylthiophene, from the bromination of 3‐butylthiophene and 3‐hexylthiophene, respectively, was carried out via a route similar to that described elsewhere 44, 45. A representative preparation of the butylated monomer is given below for the sake of completeness.…”

Synthesis, structures, and density functional theory computational study of thiophene‐containing and fluorodecorated imine‐linked polymers

“…The total energies of the four polymer building blocks resulting from the DFT calculations revealed that their stabilities were in the following order: P(T3–IPI) > P(T2FB–IPI) > P(P2T–IPI) > P(P2FB–IPI), as summarized in Table . One of the main factors that might have controlled this stability trend was the number of thiophene rings in the polymer chain . The higher the number of thiophene rings in the polymer chain was, the lower E T was, and hence, the higher the stability of the polymer was.…”

“…One of the main factors that might have controlled this stability trend was the number of thiophene rings in the polymer chain. 38 The higher the number of thiophene rings in the polymer chain was, the lower E T was, and hence, the higher the stability of the polymer was. This was attributed to the better conjugation provided by the thiophene rings.…”

Poly(3-hexylthiophene) Based Block Copolymers Prepared by “Click” Chemistry

“…Alkynyl-terminated regioregular P3HTs were synthesized by the Grignard metathesis (GRIM) as shown in Scheme 2 and according to methods detailed in the literature. 15,29,30 2,5-Dibromo-3-hexylthiophene (7), that had been prepared in two steps following published procedures, 31,32 was reacted with tertbutylmagnesium chloride to yield 2-bromo-5-magnesiochloro-3-hexylthiophene as a major product. 33 The addition of Ni(dppp)Cl 2 to the reaction mixture resulted in the formation of "living" P3HT effectively end-capped by a highly active Ni 0 group.…”

Extremely regio‐regular poly (3‐alkylthiophene)s from simplified chain‐growth Grignard metathesis polymerisations and the modification of their chain‐ends

“…3‐Bromothiophene, n‐butyl bromide, n ‐hexyl bromide, Ni(dppp)Cl 2 , N ‐bromosuccinimide (NBS), isopropylmagnesium chloride (iPMgCl, 2 M in THF), methyl magnesium bromide (3 M in THF), LiAlH 4 , N ‐methylformanilide, trifluoromethanesulfonic anhydride (TFMSA), 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DCBQ), triphenyl phosphine, and tetra‐n‐butylammonium bromide of standard grade (Aldrich, France) were used as received unless otherwise noted. The synthesis of the monomers, 2,5‐dibromo‐3‐butylthiophene and 2,5‐dibromo‐3‐hexylthiophene, from the bromination of 3‐butylthiophene and 3‐hexylthiophene, respectively, was carried out via a route similar to that described elsewhere 44, 45. A representative preparation of the butylated monomer is given below for the sake of completeness.…”