Semi-perfluoroalkylated Soluble Conjugated Polymers Based on Naphthalene Diimides

Chao Li; Zhong-yi Yuan; You-di Zhang; Chun-sheng Cai; Yu Hu; Yi-wang Chen

doi:10.11777/j.issn1000-3304.2017.17245

您当前的位置：

首页 >

文章列表页 >

Semi-perfluoroalkylated Soluble Conjugated Polymers Based on Naphthalene Diimides

Research Article | 更新时间：2021-01-26

- Semi-perfluoroalkylated Soluble Conjugated Polymers Based on Naphthalene Diimides
  增强出版
- Acta Polymerica Sinica Vol. 0, Issue 6, Pages: 712-720(2018)
- 作者机构：
  
  南昌大学化学学院　南昌 330031
- 作者简介：
- 基金信息：
- DOI：10.11777/j.issn1000-3304.2017.17245
  CLC：
- Published：2018-6，
  
  Received：28 August 2017，
  
  Revised：14 October 2017，
扫描看全文
Chao Li, Zhong-yi Yuan, You-di Zhang, Chun-sheng Cai, Yu Hu, Yi-wang Chen. Semi-perfluoroalkylated Soluble Conjugated Polymers Based on Naphthalene Diimides. [J]. Acta Polymerica Sinica 0(6):712-720(2018)
DOI：

Chao Li, Zhong-yi Yuan, You-di Zhang, Chun-sheng Cai, Yu Hu, Yi-wang Chen. Semi-perfluoroalkylated Soluble Conjugated Polymers Based on Naphthalene Diimides. [J]. Acta Polymerica Sinica 0(6):712-720(2018) DOI： 10.11777/j.issn1000-3304.2017.17245.

摘要

开发了一种高效合成关键中间体二溴萘四甲酸酐的方法. 在萘酰亚胺的N端同时引入不同类型和比例的烷基和全氟烷基(半全氟烷基)，通过多步反应合成6个具有供体-受体结构可溶液加工的共轭聚合物，并对目标聚合物化学结构、光学、电化学、热稳定性、接触角、自组装性质进行研究. 结果表明，合适的烷基和全氟烷基的比例是保证这类可溶聚合物合成的关键. 随着供体单元的供电子能力的增加，这些受体材料的吸收发生红移，吸收范围逐渐变宽；LUMO能级低至−3.90 eV，表明它们具有较强的电子接受能力；这些聚合物的分解温度都在370 °C以上，表现出良好的热稳定性；聚合物

能够自组装成纤维状；空间电荷限制电流(SCLC)测试表明，这些聚合物是典型的电子传输材料.

Abstract

Naphthalene diimides (NDIs) as excellent organic semiconductors are difficult to be synthesized

because it is difficult to separate the key intermediate 2

6-dibromo-NDI from 2-bromo-NDI. A highly efficient synthesis of 2

6-dibromo-NDI was developed in this work. Perfluoroalkylated NDIs are excellent electron transport materials

while they are unsuitable for solution process because of their poor solubility. Since semi-perfluoroalkylated conjugated compounds have much better solubility than their perfluoroalkylated counterparts

different semi-perfluoroalkyl groups were introduced to the N-terminals of NDIs

and six conjugated polymers with donor-acceptor structure were synthesized by multi-step reactions. The chemical structure

optical properties

electrochemical properties

thermal stability

contact angle

and self-assembly properties of the target polymers were studied. The results demonstrate that suitable semi-pefluoroalkyl groups are critical to the synthesis of the soluble polymers. All these polymers are readily soluble in organic solvents. Solid absorption of these polymers red-shifts compared to their solution absorption

indicating aggregation in solid state. The absorption red-shifts obviously by increasing electron donating ability of the donor unit. The optical bandgaps of the semi-perfluoroalkylated polymers are 0.3 eV lower than those of the regular polymers. The LUMO energy levels of these polymers are as low as −3.84 ~ −3.90 eV

indicating their strong electron accepting ability. The LUMO energy levels of the semi-perfluoroalkylated polymers are about 0.1 eV lower than those of NDI polymers with regular alkyl groups

which is attributed to the strong electron-withdrawing properties of their fluorine atoms. With simple spin-coating and evaporation

the polymer

can be self-assembled into ordered fibers with 500 nm in length and 30 nm in width

which is in favor of charge transfer. All these polymers have good thermal stability with their decomposing temperature above 375 °C. Their higher fluorine ratio and higher contact angles are the reflection of their water repellent properties. The mobility of these polymers is measured with space charge-limiting current (SCLC) method using the device structure of ITO/ZnO/polymer/Al

and all these polymers prove to be electron transporting materials.

关键词

半全氟烷基萘酰亚胺共轭聚合物电子传输材料

Keywords

Semi-perfluoroalkyl groupsNaphthalene diimidesConjugated polymersElectron transporting materials

references

Culloch I M, Heeney M, Bailey C, Genevicius K, Donald I M, Shkunov M, Spatrowe D, Tierney S, Wagner R, Zhang W M, Michael L, Kline R J, Michael D, Mcgehee M D, Toney M F . Nat Mater , 2006 . 5 328 - 333 . DOI:10.1038/nmat1612http://doi.org/10.1038/nmat1612 .

Chen Yiwang(陈义旺), Nie Huarong(聂华荣), Chen Lie(谌烈), Kang Yantang(康燕镗). Acta Polymerica Sinica(高分子学报), 2005, (6) : 807-812

Kang B, Lim S, Lee W H, Jo S B, Cho K . Adv Mater , 2013 . 25 5856 - 5862 . DOI:10.1002/adma.201302358http://doi.org/10.1002/adma.201302358 .

Cui Yong(崔勇), Yao Huifeng(姚惠峰), Yang Chengyi(杨晨熠), Zhang Shaoqing(张少青), Hou Jianhui(侯剑辉). Acta Polymerica Sinica(高分子学报), 2016, (11): 1468-1481

Bin Haijun(宾海军), Li Yongfang(李永舫). Acta Polymerica Sinica(高分子学报), 2017, (9): 1444-1461

Cho J H, Lee J, Xia Y, Kim B S, He Y Y, Renn M J, Frisbie T P . Nat Mater , 2008 . 7 900 - 906 . DOI:10.1038/nmat2291http://doi.org/10.1038/nmat2291 .

Kang B, Jang M, Chung Y, Kim H, Sang K K, Joon K O, Cho K . Nat Commun , 2014 . 5 4752 - 4758 . DOI:10.1038/ncomms5752http://doi.org/10.1038/ncomms5752 .

Chou K W, Yan B Y, Li R P, Li E Q, Zhao K, Dalaver H A, Steven A, Robert G, Alan B, Sigurdur T T, Hexemer A, Aram A . Adv Mater , 2013 . 25 1923 - 1929 . DOI:10.1002/adma.v25.13http://doi.org/10.1002/adma.v25.13 .

Yang Jie(杨杰), Chen Jinyang(陈金佯), Sun Yunlong(孙云龙), Shi Longxian(施龙献), Gou Yunlong(郭云龙), Wang Shuai(王帅), Liu Yunqi(刘云圻) . Acta Polymerica Sinica(高分子学报), 2017(7) : 1082-1096

Ma Feng(马峰),Wang Shirong(王世荣), Guo Junjie(郭俊杰), Li Xianggao(李祥高). Chinese J Org Chem(有机化学), 2012, 32: 497-510

Hunter S, Chen J, Anthopoulos T D . Adv Funct Mater , 2014 . 24 5969 - 5976 . DOI:10.1002/adfm.201401087http://doi.org/10.1002/adfm.201401087 .

Katz H E, Johnson J, Lovinger A J, Li W J . J Am Chem Soc , 2000 . 122 7787 - 7792 . DOI:10.1021/ja000870ghttp://doi.org/10.1021/ja000870g .

Katz H E, Lovinger A J, Johnson J, Kloc C, Li W, Lin Y Y, Dodabalapur A . Nature , 2000 . 404 478 - 481 . DOI:10.1038/35006603http://doi.org/10.1038/35006603 .

Zhang F J, Hu Y B, Torben S, Di C A, Gao K X, Christopher R M, Thomsen L, Stefan C B, Yuan W, Henning S, Zhu D B . J Am Chem Soc , 2013 . 135 2338 - 2349 . DOI:10.1021/ja311469yhttp://doi.org/10.1021/ja311469y .

Lee C Y, Kang H B, Lee W H, Kim K H, Woo H Y, Wang C, Kim B J . Adv Mater , 2015 . 27 2466 - 2471 . DOI:10.1002/adma.201405226http://doi.org/10.1002/adma.201405226 .

Bhosale S V, Jani C H, Langford S J . Chem Soc Rev , 2008 . 37 331 - 342 . DOI:10.1039/B615857Ahttp://doi.org/10.1039/B615857A .

Lei T, Wang J Y, Pei J . Chem Mater , 2014 . 26 594 - 603 . DOI:10.1021/cm4018776http://doi.org/10.1021/cm4018776 .

Mei J G, Bao Z N . Chem Mater , 2014 . 26 604 - 615 . DOI:10.1021/cm4020805http://doi.org/10.1021/cm4020805 .

Cheng X H, Prehm M, Das M K, Kain S, Baumeister U, Diele S, Leine D, Blume A, Tschierske C . J Am Chem Soc , 2003 . 125 10977 - 10996 . DOI:10.1021/ja036213ghttp://doi.org/10.1021/ja036213g .

Clark C G, Floudas G A, Lee Y J, Graf R, Spiess H W, Mullen K . J Am Chem Soc , 2009 . 131 8537 - 8547 . DOI:10.1021/ja900999fhttp://doi.org/10.1021/ja900999f .

Kang B, Kim R, Lee S B, Kwon S K, Kim Y H, Cho K . J Am Chem Soc , 2016 . 138 3679 - 3686 . DOI:10.1021/jacs.5b10445http://doi.org/10.1021/jacs.5b10445 .

Lee W, Lee C, Yu H, Kim D J, Wang C, Woo H Y, Kim B J . Adv Funct Mater , 2016 . 26 1543 - 1553 . DOI:10.1002/adfm.v26.10http://doi.org/10.1002/adfm.v26.10 .

Zong L, Xie Y, Wang C, Li J M, Li Q, Li Z . Chem Commun , 2016 . 52 11496 - 11499 . DOI:10.1039/C6CC06176Ahttp://doi.org/10.1039/C6CC06176A .

Jung B J, Lee K, Sun J, Andreou A G, Katz H E . Adv Funct Mater , 2010 . 20 2930 - 2944 . DOI:10.1002/adfm.201000655http://doi.org/10.1002/adfm.201000655 .

Banikhaled M O, Becker J D, Koppang M, Sun H R . Cryst Growth Des , 2016 . 16 1869 - 1878 . DOI:10.1021/acs.cgd.5b01291http://doi.org/10.1021/acs.cgd.5b01291 .

. J Polym Sci, Part A: Polym Chem , 2018 . 56 116 - 124 . DOI:10.1002/pola.v56.1http://doi.org/10.1002/pola.v56.1 .

Xiong K, Xiao Y . Tetrahedron Lett , 2013 . 54 3171 - 3175 . DOI:10.1016/j.tetlet.2013.04.030http://doi.org/10.1016/j.tetlet.2013.04.030 .

Chen Z H, Zheng Y, Yan H, Facchetti A . J Am Chem Soc , 2009 . 131 8 - 9 . DOI:10.1021/ja805407ghttp://doi.org/10.1021/ja805407g .

Gou X G, Watson M D . Org Lett , 2008 . 10 5333 - 5336 . DOI:10.1021/ol801918yhttp://doi.org/10.1021/ol801918y .

Yan H, Chen Z H, Zheng Y, Newan C, Quinn J R, Kastler M, Facchetti A . Nature , 2009 . 457 679 - 686 . DOI:10.1038/nature07727http://doi.org/10.1038/nature07727 .

Durban M M, Christine K L, Peter D K . Macromolecules , 2010 . 43 6348 - 6352 . DOI:10.1021/ma100997ghttp://doi.org/10.1021/ma100997g .

Choi J, Kim K H, Yu H, Lee C, Kang H, Song I, Kim Y, Oh J H, Kim B . Chem Mater , 2015 . 27 5230 - 5237 . DOI:10.1021/acs.chemmater.5b01274http://doi.org/10.1021/acs.chemmater.5b01274 .

Sirringhaus H, Tessler N, Friend R H . Science , 1998 . 280 1741 - 1744 . DOI:10.1126/science.280.5370.1741http://doi.org/10.1126/science.280.5370.1741 .

Y Zhou,Q Yan, D Zhao, J Pei . J Mater Chem , 2013 . 1 6609 - 6613 . DOI:10.1039/c3ta10864chttp://doi.org/10.1039/c3ta10864c .

Cheng Y J, Hsieh C H, Li P J, Hsu C S . Adv Funct Mater , 2011 . 21 1723 - 1732 . DOI:10.1002/adfm.201002502http://doi.org/10.1002/adfm.201002502 .

更多指标>

Views

下载量

CSCD

Alert me when the article has been cited

提交

Tools

Publicity Resources

Recent Progress of Conjugated Polymers Containing Quinoidal Structure

Design and Synthesis of Wide-bandgap Conjugated Polymers Based on 3,4-Dicyanothiophene for Efficient Organic Solar Cells

Research Progress on Aggregation Structure of Conjugated Polymers in Multicomponent Blends

Direct Arylation Polycondensation Synthesis of High Mobility Conjugated Polymers

Ladder-type Indenefluorenylene-based Conjugated Polymers with RGB Emission as Efficient Gain Media for Organic Lasers: Design, Synthesis, and Optical Gain Properties

Related Author

No data

Related Institution

School of Materials Science and Engineering, Tianjin University

Institute of Materials for Optoelectronics and New Energy, School of Materials Science and Engineering, Wuhan Institute of Technology

Institute of Polymer Optoelectronic Materials & Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology

School of Textile Materials and Engineering, Wuyi University

State Key Laboratory of Luminescent Materials and Devices, South China University of Technology

Postal code：100190
Tel：010-62588927 Email：gfzxb@iccas.ac.cn
Technical support is provided by Beijing Founder electronics co., LTD 京ICP备05002797号-8 京公网安备11010802024621
It is recommended to read the content of this site in Chrome&IE9+. Please switch to extreme mode in browser 360.
Cookies We use cookies to help provide and enhance our service and tailor content. By continuing, you agree to the use of cookies.

⁰