浏览全部资源
扫码关注微信
反应条件对Suzuki聚合制备聚芴分子量的影响
Effect of Suzuki Polymerization Conditions on the Molecular Weight of Polyfluorene
- 高分子学报 2025年56卷第2期 页码：299-305
- 作者机构：
1.青岛大学纺织服装学院 功能染料与应用技术研究院 青岛 266071
2.北京师范大学化学学院 能量转换与存储材料北京市重点实验室 北京 100875
- 作者简介：
E-mail: liuyh@qdu.edu.cn;
E-mail: zsbo@bnu.edu.cn
- 基金信息：国家重点研发计划(2022YFF0709900)
DOI：10.11777/j.issn1000-3304.2024.24228
中图分类号：- CSTR：32057.14.GFZXB.2024.7312
纸质出版日期：2025-02-20，
网络出版日期：2024-12-18，
收稿日期：2024-08-28，
录用日期：2024-09-30
- 稿件说明：
移动端阅览
宋舒悦, 王晓东, 张安东, 刘岳衡, 谷承霖, 刘亚辉, 薄志山. 反应条件对Suzuki聚合制备聚芴分子量的影响[J]. 高分子学报, 2025,56(2):299-305.
SHU-YUE SONG, XIAO-DONG WANG, AN-DONG ZHANG, YUE-HENG LIU, CHENG-LIN GU, YA-HUI LIU, ZHI-SHAN BO. Effect of Suzuki Polymerization Conditions on the Molecular Weight of Polyfluorene. [J]. Acta polymerica sinica, 2025, 56(2): 299-305.
宋舒悦, 王晓东, 张安东, 刘岳衡, 谷承霖, 刘亚辉, 薄志山. 反应条件对Suzuki聚合制备聚芴分子量的影响[J]. 高分子学报, 2025,56(2):299-305. DOI： 10.11777/j.issn1000-3304.2024.24228. CSTR： 32057.14.GFZXB.2024.7312.
SHU-YUE SONG, XIAO-DONG WANG, AN-DONG ZHANG, YUE-HENG LIU, CHENG-LIN GU, YA-HUI LIU, ZHI-SHAN BO. Effect of Suzuki Polymerization Conditions on the Molecular Weight of Polyfluorene. [J]. Acta polymerica sinica, 2025, 56(2): 299-305. DOI： 10.11777/j.issn1000-3304.2024.24228. CSTR： 32057.14.GFZXB.2024.7312.
摘要
聚芴作为一类典型的有机共轭半导体材料，在有机光电器件制备中
得到广泛应用，其分子量对光电性质具有显著影响. 本研究聚焦于聚芴材料的制备过程，采用Suzuki反应制备聚芴，通过调控溶剂(四氢呋喃/水、甲苯/水、邻二甲苯/水、二氯甲烷/水)，碱的种类(碳酸钾、碳酸氢钾、氢氧化钾、磷酸钾)，催化剂(Pd(PPh
3
)
4
、Pd
2
(dba)
3
/P(
o
-Tol)
3
、Pd(OAc)
2
/P(
o
-tol)
3
、PdCl
2
(dppf)、PdCl
2
(PPh
3
)
2
)，以及化学计量比（1:1，1:0.99，1:1.01）等反应条件，深入研究了这些因素对聚芴类材料分子量的影响. 研究结果表明，增强有机溶剂与水的混溶性，选用中等强度的无机碱，采用二价钯催化体系，并严格控制反应物的投料比为1:1，有助于合成高分子量的聚芴.
Abstract
Polyfluorene is a typical class of organic conjugated semiconductor materials
which is widely used in the preparation of organic optoelectronic devices
and its molecular weight has a significant effect on the optoelectronic properties. In this study
we focused on the preparation of polyfluorene materials and investigated the effect on the molecular weight of polyfluorene materials by controlling the reaction conditions
such as solvent (tetrahydrofuran/H
2
O
toluene/H
2
O
o
-xylene/H
2
O
dichloromethane/H
2
O)
base (K
2
CO
3
KHCO
3
KOH
K
3
PO
4
)
catalyst (Pd(PPh
3
)
4
Pd
2
(dba)
3
/P(
o
-Tol)
3
Pd(OAc)
2
/P(
o
-tol)
3
PdCl
2
(dppf)
PdCl
2
(PPh
3
)
2
) and stoichiometric ratio (1:1
1:0.99
1:1.01). Our results show that the obtained polyfluorene tend to display high molecular weight by increasing the miscibility of organic solvents with water
selecting medium strength inorganic bases
Pd(Ⅱ) catalytic system
and strictly controlling the reaction feed ratio (1:1).
关键词
Suzuki聚合分子量聚芴反应条件共轭聚合物
Keywords
Suzuki polymerizationMolecular weightPolyfluoreneReaction conditionsConjugated polymer
references
Lu H. Z.; Li X. L.; Lei Q. Q.Conjugated conductive polymer materials and its applications: a mini-review. Front. Chem., 2021, 9, 732132. doi:10.3389/fchem.2021.732132http://dx.doi.org/10.3389/fchem.2021.732132
Wang Y. F.; Meng H. M.; Song G. S.; Li Z. H.; Zhang X. B.Conjugated-polymer-based nanomaterials for photothermal therapy. ACS Appl. Polym. Mater., 2020, 2(10), 4258-4272. doi:10.1021/acsapm.0c00680http://dx.doi.org/10.1021/acsapm.0c00680
Yu Z. D.; Lu Y.; Wang J. Y.; Pei J.Conformation control of conjugated polymers. Chem.-Eur. J., 2020, 26(69), 16194-16205. doi:10.1002/chem.202000220http://dx.doi.org/10.1002/chem.202000220
Zhang D. D.; Huang T. Y.; Duan L.Emerging self-emissive technologies for flexible displays. Adv. Mater., 2020, 32(15), 1902391. doi:10.1002/adma.201902391http://dx.doi.org/10.1002/adma.201902391
黄飞, 薄志山, 耿延候, 王献红, 王利祥, 马於光, 侯剑辉, 胡文平, 裴坚, 董焕丽, 王树, 李振, 帅志刚, 李永舫, 曹镛. 光电高分子材料的研究进展. 高分子学报, 2019, 50(10), 988-1046. doi:10.11777/j.issn1000-3304.2019.19110http://dx.doi.org/10.11777/j.issn1000-3304.2019.19110
Wang Y. J.; Yu G. H.Conjugated polymers: from synthesis, transport properties, to device applications. J. Polym. Sci. Part B Polym. Phys., 2019, 57(23), 1557-1558. doi:10.1002/polb.24911http://dx.doi.org/10.1002/polb.24911
Grimsdale A. C.; Leok Chan K.; Martin R. E.; Jokisz P. G.; Holmes A. B.Synthesis of light-emitting conjugated polymers for applications in electroluminescent devices. Chem. Rev., 2009, 109(3), 897-1091. doi:10.1021/cr000013vhttp://dx.doi.org/10.1021/cr000013v
Kurdyukova I. V.; Ishchenko A. A.Organic dyes based on fluorene and its derivatives. Russ. Chem. Rev., 2012, 81(3), 258-290. doi:10.1070/rc2012v081n03abeh004211http://dx.doi.org/10.1070/rc2012v081n03abeh004211
Sainova D.; Fujikawa H.; Scherf U.; Neher D.The effect of hole traps on the performance of single layer polymer light emitting diodes. Opt. Mater., 1999, 12(2-3), 387-390. doi:10.1016/s0925-3467(99)00033-6http://dx.doi.org/10.1016/s0925-3467(99)00033-6
Sirringhaus, H. 25th Anniversary article: Organic field-effect transistors: the path beyond amorphous silicon. Adv. Mater., 2014, 26(9), 1319-1335. doi:10.1002/adma.201304346http://dx.doi.org/10.1002/adma.201304346
Kline R. J.; McGehee M. D.; Kadnikova E. N.; Liu J.; Fréchet J. M. J.Controlling the field-effect mobility of regioregular polythiophene by changing the molecular weight. Adv. Mater., 2003, 15(18), 1519-1522. doi:10.1002/adma.200305275http://dx.doi.org/10.1002/adma.200305275
Pei D. D.; Wang Z. L.; Peng Z. X.; Zhang J. D.; Deng Y. F.; Han Y.; Ye L.; Geng Y. H.Impact of molecular weight on the mechanical and electrical properties of a high-mobility diketopyrrolopyrrole-based conjugated polymer. Macromolecules, 2020, 53(11), 4490-4500. doi:10.1021/acs.macromol.0c00209http://dx.doi.org/10.1021/acs.macromol.0c00209
Zhao K. F.; Zhang T.; Zhang L.; Li J. H.; Li H. X.; Wu F.; Chen Y.; Zhang Q.; Han Y. C.Role of molecular weight in microstructural transition and its correlation to the mechanical and electrical properties of P(NDI2OD-T2) thin films. Macromolecules, 2021, 54(21), 10203-10215. doi:10.1021/acs.macromol.1c01481http://dx.doi.org/10.1021/acs.macromol.1c01481
Choi J.; Kim W.; Kim D.; Kim S.; Chae J.; Choi S. Q.; Kim F. S.; Kim T. S.; Kim B. J.Importance of critical molecular weight of semicrystalline n-type polymers for mechanically robust, efficient electroactive thin films. Chem. Mater., 2019, 31(9), 3163-3173. doi:10.1021/acs.chemmater.8b05114http://dx.doi.org/10.1021/acs.chemmater.8b05114
Wu Y. S.; Ding M. M.; Wang J.; Zhao B.; Wu Z. Q.; Zhao P.; Tian D. L.; Ding Y.; Hu A. G.Controlled step-growth polymerization. CCS Chem., 2020, 2(2), 64-70. doi:10.31635/ccschem.020.202000126http://dx.doi.org/10.31635/ccschem.020.202000126
李韦伟. 给体/受体双缆型共轭聚合物材料及其单组分有机太阳能电池器件. 高分子学报, 2019, 50(3), 209-218. doi:10.11777/j.issn1000-3304.2019.18212http://dx.doi.org/10.11777/j.issn1000-3304.2019.18212
Fair R. A.; Xie R. X.; Lee Y.; Colby R. H.; Gomez E. D.Molecular weight characterization of conjugated polymers through gel permeation chromatography and static light scattering. ACS Appl. Polym. Mater., 2021, 3(9), 4572-4578. doi:10.1021/acsapm.1c00647http://dx.doi.org/10.1021/acsapm.1c00647
Heffner G. W.; Dahman S. J.; Pearson D. S.; Gettinger C. L.The effect of molecular weight and crystallinity on the conductivity of a conducting polymer. Polymer, 1993, 34(15), 3155-3159. doi:10.1016/0032-3861(93)90383-lhttp://dx.doi.org/10.1016/0032-3861(93)90383-l
Fukuda M.; Sawada K.; Yoshino K.Fusible conducting poly(9-alkylfluorene) and poly(9,9-dialkylfluorene) and their characteristics. Jpn. J. Appl. Phys., 1989, 28(8), L1433-L1435. doi:10.1143/jjap.28.l1433http://dx.doi.org/10.1143/jjap.28.l1433
McCullough R. D.; Lowe R. D.Enhanced electrical conductivity in regioselectively synthesized poly(3-alkylthiophenes). J. Chem. Soc., Chem. Commun., 1992, (1), 70-72. doi:10.1039/c39920000070http://dx.doi.org/10.1039/c39920000070
Feast W. J.; Tsibouklis J.; Pouwer K. L.; Groenendaal L.; Meijer E. W.Synthesis, processing and material properties of conjugated polymers. Polymer, 1996, 37(22), 5017-5047. doi:10.1016/0032-3861(96)00439-9http://dx.doi.org/10.1016/0032-3861(96)00439-9
Rehahn M.; Schlüter A. D.; Wegner G.; Feast W. J.Soluble poly(para-phenylene)s. 1. Extension of the Yamamoto synthesis to dibromobenzenes substituted with flexible side chains. Polymer, 1989, 30(6), 1054-1059. doi:10.1016/0032-3861(89)90078-5http://dx.doi.org/10.1016/0032-3861(89)90078-5
Komorowska-Durka M.; Dimitrakis G.; Bogdał D.; Stankiewicz A. I.; Stefanidis G. D.A concise review on microwave-assisted polycondensation reactions and curing of polycondensation polymers with focus on the effect of process conditions. Chem. Eng. J., 2015, 264, 633-644. doi:10.1016/j.cej.2014.11.087http://dx.doi.org/10.1016/j.cej.2014.11.087
Selvaraj V.; Abimannan P.; Rajendran V.Ultrasound assisted arylation of benzyl alcohol with 4-nitrochlorobenzene under a new multi-site phase-transfer catalyst in solid-liquid condition. Ultrason. Sonochem., 2014, 21(5), 1805-1814. doi:10.1016/j.ultsonch.2014.04.010http://dx.doi.org/10.1016/j.ultsonch.2014.04.010
Ma Z. J.; Cheng L.; Weng X. Y.; Gao Y.; Huang J. X.Study on phase transfer catalyst used in the synthesis of sodium isobutyl xanthate. Minerals, 2021, 11(8), 850. doi:10.3390/min11080850http://dx.doi.org/10.3390/min11080850
Li B.; Wang C. P.; Chen G.; Zhang Z. Q.Palladium-phosphinous acid complexes catalyzed Suzuki cross-coupling reaction of heteroaryl bromides with phenylboronic acid in water/alcoholic solvents. J. Environ. Sci., 2013, 25(6), 1083-1088. doi:10.1016/s1001-0742(12)60132-6http://dx.doi.org/10.1016/s1001-0742(12)60132-6
Choi S. J.; Kuwabara J.; Kanbara T.Microwave-assisted polycondensation via direct arylation of3,4-ethylenedioxythiophene with 9,9-dioctyl-2,7-dibromofluorene. ACS Sustainable Chem. Eng., 2013, 1(8), 878-882. doi:10.1021/sc4000576http://dx.doi.org/10.1021/sc4000576
Nehls B. S.; Asawapirom U.; Füldner S.; Preis E.; Farrell T.; Scherf U.Semiconducting polymers via microwave-assisted suzuki and stille cross-coupling reactions. Adv. Funct. Mater., 2004, 14(4), 352-356. doi:10.1002/adfm.200400010http://dx.doi.org/10.1002/adfm.200400010
Banik B. K.; Banerjee B.; Kaur G.; Saroch S.; Kumar R.Tetrabutylammonium bromide (TBAB) catalyzed synthesis of bioactive heterocycles. Molecules, 2020, 25(24), 5918. doi:10.3390/molecules25245918http://dx.doi.org/10.3390/molecules25245918
Yamamoto Y.; Nogi K.; Yorimitsu H.; Osuka A.Base-free palladium-catalyzed hydrodechlorination of aryl chlorides with pinacol borane. ChemistrySelect, 2017, 2(4), 1723-1727. doi:10.1002/slct.201700189http://dx.doi.org/10.1002/slct.201700189
Sanhueza I. A.; Klauck F. J. R.; Senol E.; Keaveney S. T.; Sperger T.; Schoenebeck F.Base-free cross-couplings of aryl diazonium salts in methanol: PdII-alkoxy as reactivity-controlling intermediate. Angew. Chem. Int. Ed., 2021, 60(13), 7007-7012. doi:10.1002/anie.202014842http://dx.doi.org/10.1002/anie.202014842
Niwa T.; Uetake Y.; Isoda M.; Takimoto T.; Nakaoka M.; Hashizume D.; Sakurai H.; Hosoya T.Lewis acid-mediated Suzuki–Miyaura cross-coupling reaction. Nat. Catal., 2021, 4, 1080-1088. doi:10.1038/s41929-021-00719-6http://dx.doi.org/10.1038/s41929-021-00719-6
Cox P. A.; Reid M.; Leach A. G.; Campbell A. D.; King E. J.; Lloyd-Jones G. C.Base-catalyzed aryl-B(OH)2 revisitedprotodeboronation: from concerted proton transfer to liberation of a transient aryl anion. J. Am. Chem. Soc., 2017, 139(37), 13156-13165. doi:10.1021/jacs.7b07444http://dx.doi.org/10.1021/jacs.7b07444
Braga A. A. C.; Morgon N. H.; Ujaque G.; Maseras F.Computational characterization of the role of the base in the Suzuki-Miyaura cross-coupling reaction. J. Am. Chem. Soc., 2005, 127(25), 9298-9307. doi:10.1021/ja050583ihttp://dx.doi.org/10.1021/ja050583i
Murage J.; Eddy J. W.; Zimbalist J. R.; McIntyre T. B.; Wagner Z. R.; Goodson F. E.Effect of reaction parameters on the molecular weights of polymers formed in a suzuki polycondensation. Macromolecules, 2008, 41(20), 7330-7338. doi:10.1021/ma801275yhttp://dx.doi.org/10.1021/ma801275y
欧阳昆冰, 席振峰. 碱在过渡金属催化的有机化学反应中的作用. 化学学报, 2013, 71(1), 13-25. doi:10.6023/A12110984http://dx.doi.org/10.6023/A12110984
Murray J. I.; Zhang L.; Simon A.; Silva Elipe M. V.; Wei C. S.; Caille S.; Parsons A. T.Kinetic and mechanistic investigations to enable a key suzuki coupling for sotorasib manufacture─what a difference a base makes. Org. Process Res. Dev., 2023, 27(1), 198-205. doi:10.1021/acs.oprd.2c00332http://dx.doi.org/10.1021/acs.oprd.2c00332
Hiltunen K.; Seppälä J. V.; Härkönen M.Effect of catalyst and polymerization conditions on the preparation of low molecular weight lactic acid polymers. Macromolecules, 1997, 30(3), 373-379. doi:10.1021/ma960919whttp://dx.doi.org/10.1021/ma960919w
Jeon J. W.; Hwang Y. J.Flow synthesis of conjugated polymers: exploring the effects of solvent and catalyst on molecular weight. Polym. Chem., 2023, 14(47), 5200-5207. doi:10.1039/d3py00917chttp://dx.doi.org/10.1039/d3py00917c
Yang X. W.; Ji Q. Q.; Liu J. X.; Liu Y. L.In situ supramolecular polymerization via organometallic-catalyzed macromolecular metamorphosis. CCS Chem., 2023, 5(3), 761-771. doi:10.31635/ccschem.022.202201936http://dx.doi.org/10.31635/ccschem.022.202201936
0
浏览量
133
下载量
0
CSCD
- 网络PDF下载
- Enhanced-PDF下载
- BibTeX下载
- Endnote下载
- RefMan 下载
- NoteExpress下载
- NoteFirst下载
关联资源
相关文章
相关作者
相关机构
- 地址：北京中关村北一街2号（北京2709信箱） 邮编：100190
- 联系电话：010-62588927 Email：gfzxb@iccas.ac.cn
- 技术支持由北京北大方正电子有限公司提供 京ICP备05002797号-8
京公网安备11010802024621 - 本系统建议在Chrome、 IE9+ 以上版本浏览器阅读本站内容，360浏览器请切换至极速模式
- Cookies帮助我们提供服务并提供个性化体验。使用本网站，即表示您同意我们使用Cookies