Suzuki-Miyaura catalyst-transfer polycondensation of triolborate-type fluorene monomer: toward rapid access to polyfluorene-containing block and graft copolymers from various macroinitiators
In this study, we demonstrated that the Suzuki-Miyaura catalyst transfer polycondensation (SCTP) of the triolborate-type fluorene monomer, viz . potassium 2-(7-bromo-9,9-dihexyl-9 H -fluorene-2-yl)triolborate, can be an efficient and versatile approach to the precise synthesis of poly[2,7-(9,9-dihex...
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Published in | Polymer chemistry Vol. 11; no. 42; pp. 6832 - 6839 |
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Main Authors | , , , , , , , |
Format | Journal Article |
Language | English |
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Royal Society of Chemistry
14.11.2020
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Abstract | In this study, we demonstrated that the Suzuki-Miyaura catalyst transfer polycondensation (SCTP) of the triolborate-type fluorene monomer,
viz
. potassium 2-(7-bromo-9,9-dihexyl-9
H
-fluorene-2-yl)triolborate, can be an efficient and versatile approach to the precise synthesis of poly[2,7-(9,9-dihexylfluorene)]s (PFs) and PF-containing block and graft copolymers. SCTP of the triolborate-type monomer proceeded rapidly in a THF/H
2
O mixed solvent at −10 °C using an iodobenzene derivative/Pd
2
(dba)
3
·CHCl
3
/
t
-Bu
3
P initiating system. Kinetic and post-polymerization experiments revealed that SCTP proceeded
via
the chain-growth and living polymerization mechanisms. The most important feature of the present polymerization system is that only a small amount of base and water can sufficiently promote the reaction. The well-controlled nature of this polymerization system enabled the synthesis of high-molecular-weight PFs (
M
n
= 5-69 kg mol
−1
) with narrow dispersity (
M
= 1.14-1.38) and α-end-functionalized PFs. Most importantly, PF-containing block and graft copolymers were successfully synthesized, beginning with various iodobenzene-functionalized macroinitiators; this was difficult to achieve by the conventional SCTP of pinacolboronate-type fluorene monomer. One of the key factors for the successful block and graft copolymer syntheses is the reduced water content in the polymerization medium, which suppressed the potential precipitation/aggregation of the macroinitiators.
We demonstrated that the Suzuki-Miyaura catalyst transfer polycondensation of a triolborate-type fluorene monomer can be an efficient and versatile approach to the synthesis of polyfluorenes (PFs) and PF-containing block and graft copolymers. |
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AbstractList | In this study, we demonstrated that the Suzuki–Miyaura catalyst transfer polycondensation (SCTP) of the triolborate-type fluorene monomer, viz. potassium 2-(7-bromo-9,9-dihexyl-9H-fluorene-2-yl)triolborate, can be an efficient and versatile approach to the precise synthesis of poly[2,7-(9,9-dihexylfluorene)]s (PFs) and PF-containing block and graft copolymers. SCTP of the triolborate-type monomer proceeded rapidly in a THF/H2O mixed solvent at −10 °C using an iodobenzene derivative/Pd2(dba)3·CHCl3/t-Bu3P initiating system. Kinetic and post-polymerization experiments revealed that SCTP proceeded via the chain-growth and living polymerization mechanisms. The most important feature of the present polymerization system is that only a small amount of base and water can sufficiently promote the reaction. The well-controlled nature of this polymerization system enabled the synthesis of high-molecular-weight PFs (Mn = 5–69 kg mol−1) with narrow dispersity (ĐM = 1.14–1.38) and α-end-functionalized PFs. Most importantly, PF-containing block and graft copolymers were successfully synthesized, beginning with various iodobenzene-functionalized macroinitiators; this was difficult to achieve by the conventional SCTP of pinacolboronate-type fluorene monomer. One of the key factors for the successful block and graft copolymer syntheses is the reduced water content in the polymerization medium, which suppressed the potential precipitation/aggregation of the macroinitiators. In this study, we demonstrated that the Suzuki–Miyaura catalyst transfer polycondensation (SCTP) of the triolborate-type fluorene monomer, viz . potassium 2-(7-bromo-9,9-dihexyl-9 H -fluorene-2-yl)triolborate, can be an efficient and versatile approach to the precise synthesis of poly[2,7-(9,9-dihexylfluorene)]s (PFs) and PF-containing block and graft copolymers. SCTP of the triolborate-type monomer proceeded rapidly in a THF/H 2 O mixed solvent at −10 °C using an iodobenzene derivative/Pd 2 (dba) 3 ·CHCl 3 / t -Bu 3 P initiating system. Kinetic and post-polymerization experiments revealed that SCTP proceeded via the chain-growth and living polymerization mechanisms. The most important feature of the present polymerization system is that only a small amount of base and water can sufficiently promote the reaction. The well-controlled nature of this polymerization system enabled the synthesis of high-molecular-weight PFs ( M n = 5–69 kg mol −1 ) with narrow dispersity ( Đ M = 1.14–1.38) and α-end-functionalized PFs. Most importantly, PF-containing block and graft copolymers were successfully synthesized, beginning with various iodobenzene-functionalized macroinitiators; this was difficult to achieve by the conventional SCTP of pinacolboronate-type fluorene monomer. One of the key factors for the successful block and graft copolymer syntheses is the reduced water content in the polymerization medium, which suppressed the potential precipitation/aggregation of the macroinitiators. In this study, we demonstrated that the Suzuki-Miyaura catalyst transfer polycondensation (SCTP) of the triolborate-type fluorene monomer, viz . potassium 2-(7-bromo-9,9-dihexyl-9 H -fluorene-2-yl)triolborate, can be an efficient and versatile approach to the precise synthesis of poly[2,7-(9,9-dihexylfluorene)]s (PFs) and PF-containing block and graft copolymers. SCTP of the triolborate-type monomer proceeded rapidly in a THF/H 2 O mixed solvent at −10 °C using an iodobenzene derivative/Pd 2 (dba) 3 ·CHCl 3 / t -Bu 3 P initiating system. Kinetic and post-polymerization experiments revealed that SCTP proceeded via the chain-growth and living polymerization mechanisms. The most important feature of the present polymerization system is that only a small amount of base and water can sufficiently promote the reaction. The well-controlled nature of this polymerization system enabled the synthesis of high-molecular-weight PFs ( M n = 5-69 kg mol −1 ) with narrow dispersity ( M = 1.14-1.38) and α-end-functionalized PFs. Most importantly, PF-containing block and graft copolymers were successfully synthesized, beginning with various iodobenzene-functionalized macroinitiators; this was difficult to achieve by the conventional SCTP of pinacolboronate-type fluorene monomer. One of the key factors for the successful block and graft copolymer syntheses is the reduced water content in the polymerization medium, which suppressed the potential precipitation/aggregation of the macroinitiators. We demonstrated that the Suzuki-Miyaura catalyst transfer polycondensation of a triolborate-type fluorene monomer can be an efficient and versatile approach to the synthesis of polyfluorenes (PFs) and PF-containing block and graft copolymers. |
Author | Isono, Takuya Yamamoto, Yasunori Kobayashi, Saburo Yamamoto, Takuya Fujiwara, Kaiyu Satoh, Toshifumi Jiang, Dai-Hua Tajima, Kenji |
AuthorAffiliation | Hokkaido University Research and Development Center of Smart Textile Technology National Taipei University of Technology Institute of Polymer Science and Engineering Faculty of Engineering and Graduate School of Chemical Sciences and Engineering National Taiwan University Graduate School of Chemical Sciences and Engineering Institute of Organic and Polymeric Materials |
AuthorAffiliation_xml | – name: Research and Development Center of Smart Textile Technology – name: Institute of Organic and Polymeric Materials – name: National Taiwan University – name: Faculty of Engineering and Graduate School of Chemical Sciences and Engineering – name: Institute of Polymer Science and Engineering – name: Hokkaido University – name: National Taipei University of Technology – name: Graduate School of Chemical Sciences and Engineering |
Author_xml | – sequence: 1 givenname: Saburo surname: Kobayashi fullname: Kobayashi, Saburo – sequence: 2 givenname: Kaiyu surname: Fujiwara fullname: Fujiwara, Kaiyu – sequence: 3 givenname: Dai-Hua surname: Jiang fullname: Jiang, Dai-Hua – sequence: 4 givenname: Takuya surname: Yamamoto fullname: Yamamoto, Takuya – sequence: 5 givenname: Kenji surname: Tajima fullname: Tajima, Kenji – sequence: 6 givenname: Yasunori surname: Yamamoto fullname: Yamamoto, Yasunori – sequence: 7 givenname: Takuya surname: Isono fullname: Isono, Takuya – sequence: 8 givenname: Toshifumi surname: Satoh fullname: Satoh, Toshifumi |
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Notes | 1 H NMR, DOSY NMR, SEC, and MALDI-TOF MS). See DOI 10.1039/d0py01127d Electronic supplementary information (ESI) available: Experimental procedures and additional data |
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Snippet | In this study, we demonstrated that the Suzuki-Miyaura catalyst transfer polycondensation (SCTP) of the triolborate-type fluorene monomer,
viz
. potassium... In this study, we demonstrated that the Suzuki–Miyaura catalyst transfer polycondensation (SCTP) of the triolborate-type fluorene monomer, viz . potassium... In this study, we demonstrated that the Suzuki–Miyaura catalyst transfer polycondensation (SCTP) of the triolborate-type fluorene monomer, viz. potassium... |
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SubjectTerms | Block copolymers Catalysts Chemical synthesis Chloroform Copolymers Graft copolymers Moisture content Monomers NMR Nuclear magnetic resonance Polymer chemistry Polymerization |
Title | Suzuki-Miyaura catalyst-transfer polycondensation of triolborate-type fluorene monomer: toward rapid access to polyfluorene-containing block and graft copolymers from various macroinitiators |
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