Loading...
Please wait, while we are loading the content...
Similar Documents
Suzuki–Miyaura Catalyst-Transfer Polycondensation of Triolborate-Type Carbazole Monomers
| Content Provider | MDPI |
|---|---|
| Author | Kobayashi, Saburo Ashiya, Mayoh Yamamoto, Takuya Tajima, Kenji Yamamoto, Yasunori Isono, Takuya Satoh, Toshifumi |
| Copyright Year | 2021 |
| Description | Herein, we report the Suzuki–Miyaura catalyst-transfer polycondensation (SCTP) of triolborate-type carbazole monomers, i.e., potassium 3-(6-bromo-9-(2-octyldodecyl)-9H-carbazole-2-yl)triolborate (M1) and potassium 2-(7-bromo-9-(2-octyldodecyl)-9H-carbazole-2-yl) triolborate (M2), as an efficient and versatile approach for precisely synthesizing poly[9-(2-octyldodecyl)-3,6-carbazole] (3,6-PCz) and poly[9-(2-octyldodecyl)-2,7-carbazole] (2,7-PCz), respectively. The SCTP of triolborate-type carbazole monomers was performed in a mixture of $THF/H_{2}$O using an initiating system consisted of 4-iodobenzyl alcohol, $Pd_{2}(dba)_{3}•CHCl_{3}$, and $t-Bu_{3}$P. In the SCTP of M1, cyclic by-product formation was confirmed, as reported for the corresponding pinacolboronate-type monomer. By optimizing the reaction temperature and reaction time, we successfully synthesized linear end-functionalized 3,6-PCz for the first time. The SCTP of M2 proceeded with almost no side reaction, yielding 2,7-PCz with a functional initiator residue at the α-chain end. Kinetic and block copolymerization experiments demonstrated that the SCTP of M2 proceeded in a chain-growth and controlled/living polymerization manner. This is a novel study on the synthesis of 2,7-PCz via SCTP. By taking advantage of the well-controlled nature of this polymerization system, we demonstrated the synthesis of high-molecular-weight 2,7-PCzs $(M_{n}$ = 5–38 kg $mol^{−1}$) with a relatively narrow $Ð_{M}$ (1.35–1.48). Furthermore, we successfully synthesized fluorene/carbazole copolymers as well as 2,7-PCz-containing diblock copolymers, demonstrating the versatility of the present polymerization system as a novel synthetic strategy for well-defined polycarbazole-based materials. |
| Starting Page | 4168 |
| e-ISSN | 20734360 |
| DOI | 10.3390/polym13234168 |
| Journal | Polymers |
| Issue Number | 23 |
| Volume Number | 13 |
| Language | English |
| Publisher | MDPI |
| Publisher Date | 2021-11-28 |
| Access Restriction | Open |
| Subject Keyword | Polymers Polymer Science Π-conjugated Polymer Polycarbazole Catalyst-transfer Polycondensation |
| Content Type | Text |
| Resource Type | Article |
