Synthesis and Luminescent Properties of Polyfluorenes with an Orange Emissive End Group

Zhang Shu-ren; Yao Bing; Zhang Zi-long; Zhang Bao-hua; Li Xiao; Cheng Yan-xiang

doi:10.11777/j.issn1000-3304.2016.16026

您当前的位置：

首页 >

文章列表页 >

Synthesis and Luminescent Properties of Polyfluorenes with an Orange Emissive End Group

Research Article | 更新时间：2021-03-19

- Synthesis and Luminescent Properties of Polyfluorenes with an Orange Emissive End Group
- Acta Polymerica Sinica Issue 10, Pages: 1359-1367(2016)
- 作者机构：
  
  1.中国科学院长春应用化学研究所高分子物理与化学国家重点实验室长春 130022
  2.中国科学院大学北京 100049
- 作者简介：
- 基金信息：
- DOI：10.11777/j.issn1000-3304.2016.16026
  CLC：
- Published：2016-10，
  
  Received：20 January 2016，
  
  Revised：24 February 2016，
扫描看全文
Zhang Shu-ren, Yao Bing, Zhang Zi-long, Zhang Bao-hua, Li Xiao, Cheng Yan-xiang. Synthesis and Luminescent Properties of Polyfluorenes with an Orange Emissive End Group. [J]. Acta Polymerica Sinica (10):1359-1367(2016)
DOI：

Zhang Shu-ren, Yao Bing, Zhang Zi-long, Zhang Bao-hua, Li Xiao, Cheng Yan-xiang. Synthesis and Luminescent Properties of Polyfluorenes with an Orange Emissive End Group. [J]. Acta Polymerica Sinica (10):1359-1367(2016) DOI： 10.11777/j.issn1000-3304.2016.16026.

摘要

含溴橙光化合物与双（三环己基膦）钯（0）进行氧化加成反应，合成了相应的芳基钯（Ⅱ）配合物.在加热条件下，该配合物可以引发AB型芴单体聚合，得到端基为橙光芳基基团的聚芴共轭聚合物.含溴橙光化合物与不同配体钯（0）配合物组成催化体系，原位引发聚合，同样可以制备上述端基结构明确的共轭聚合物.其中，以三（邻甲基苯基）膦或卡宾化合物为辅助配体时，室温下即可引发AB型芴单体进行催化剂转移聚合.卡宾化合物为辅助配体时，可以获得

为7.48×10

的高分子量聚芴.MALDI-TOF分析证实，聚合物的一个端基是来自催化剂钯配合物中的橙光芳基基团，另一端基为Br/H原子.聚合物光致发光（PL）光谱主要表现为聚芴单元的蓝色荧光发射.电致发光（EL）光谱表明，聚合物在低分子量时表现为橙红光发射，而在高分子量时，能够得到白光发射.在数均分子量

为7.48×10

时，聚合物可实现纯白光发射，国际色坐标CIE为（0.31，0.32）.

Abstract

An Aryl palladium complex was synthesized by oxidative addition of aryl bromide-containing orange emissive group (OG-Br) to Pd(PCy

)

.The complex is thermally stable in air and can initiate the polymerization of AB-type fluorene monomer at elevated temperature to get polyfluorene with defined aryl end group.Similar conjugated polymers can also be prepared by employing the aryl palladium complexes

in situ

generated from OG-Br/Pd(0)-species as initiators.Among them

with P(o-tol)

-heterocyclic carbene as the ancillary ligand

catalyst-transfer polymerization of AB-type fluorene monomers can be achieved at room temperature.The complex ligated by

-heterocyclic carbene shows better activity in the catalyst-transfer polymerization

which offer the polyfluorene with high molecular weight of up to 7.48×10

.MALDI-TOF mass spectra confirm that the polymers bear the orange emissive group derived from the aryl complex at one end and a Br/H atom at the other end.Photoluminescence (PL) spectra of the polymers show dominant blue emission from the polyfluorene backbone.In contrast

electroluminescence (EL) spectra exhibit orange or white emission

respectively

resulting from a difference of the molecular weight.With the number average molecular weight (

) of 7.48×10

the polymer emits pure white light with simultaneous blue and orange emission and CIE coordinates of (0.31

0.32).

关键词

催化剂转移聚合芳基钯化合物聚芴光致发光电致发光

Keywords

Catalyst-transfer polymerizationAryl palladium complexesPolyfluorenePhotoluminescenceElectroluminescence

references

A C Grimsdale , K L Chan , R E Martin , P G Jokisz , A B Holmes . . Chem Rev , 2009 . 109 897 - 1091 . DOI:10.1021/cr000013vhttp://doi.org/10.1021/cr000013v.

Y J Cheng , S H Yang , C S Hsu . . Chem Rev , 2009 . 109 5868 - 5923 . DOI:10.1021/cr900182shttp://doi.org/10.1021/cr900182s.

Jing(李静) Li , Hongwei(付宏伟) Fu , Pan(胡盼) Hu , Zilong(张子龙) Zhang , Xiao(李晓) Li , Yanxiang(程延祥) Cheng . . Acta Polymerica Sinica(高分子学报) , 2013 . ( 9 ): 1143 - 1150.

M F Liu , YL Chen , B Zhu , Y Han , W G Huang , C Du , Z S Bo . . Chinese J Polym Sci , 2012 . 30 405 - 414 . DOI:10.1007/s10118-012-1131-5http://doi.org/10.1007/s10118-012-1131-5.

Q J Zhao , W H Wu , Q L Niu , J B Peng . . Chinese J Polym Sci , 2009 . 27 611 - 619 . DOI:10.1142/S0256767909004308http://doi.org/10.1142/S0256767909004308.

Hui(李辉) Li , Bin(赵斌) Zhao , Ping(沈平) Shen , Meixiu(万梅秀) Wan , Songting(谭松庭) Tan . . Acta Polymerica Sinica(高分子学报) , 2010 . ( 5 ): 501 - 507.

Chunyang(覃春杨) Qin , Feng(刘烽) Liu , Bo(彭波) Peng , Wei(黄维) Huang , Wei(韦玮) Wei . . Acta Polymerica Sinica(高分子学报) , 2008 . ( 6 ): 537 - 543.

Chunlei(卞春雷) Bian , Guoxin(江国新) Jiang , Yanxiang(程延祥) Cheng , Zhiyuan(谢志元) Xie , Lixiang(王利祥) Wang . . Acta Polymerica Sinica(高分子学报) , 2012 . ( 3 ): 334 - 343.

S Y Shao , J Q Ding , L X Wang , X B Jing , F S Wang . . J Am Chem Soc , 2012 . 134 15189 - 15192 . DOI:10.1021/ja305634jhttp://doi.org/10.1021/ja305634j.

S Y Shao , J Q Ding , L X Wang , X B Jing , F S Wang . . J Am Chem Soc , 2012 . 134 20290 - 20293 . DOI:10.1021/ja310158jhttp://doi.org/10.1021/ja310158j.

B B Jiang , J B Fang , Y Yang , Q Ren , W Y Wang , J J Hao . . Eur Polym J , 2006 . 42 179 - 187 . DOI:10.1016/j.eurpolymj.2005.07.016http://doi.org/10.1016/j.eurpolymj.2005.07.016.

F C Krebs , R B Nyberg , Mikkel Jorgensen . . Chem Mater , 2004 . 16 1313 - 1318 . DOI:10.1021/cm035205whttp://doi.org/10.1021/cm035205w.

M P Nikiforov , B Lai , W Chen , S Chen , R D Schaller , J Strzalka , J Maser , S B Darling . . Energy Environ Sci , 2013 . 6 1513 - 1520 . DOI:10.1039/c3ee40556ghttp://doi.org/10.1039/c3ee40556g.

T Yokozawa , A Yokoyama . . Chem Rev , 2009 . 109 5595 - 5619 . DOI:10.1021/cr900041chttp://doi.org/10.1021/cr900041c.

A Yokoyama , T Yokozawa . . Macromolecules , 2007 . 40 4093 - 4101 . DOI:10.1021/ma061357bhttp://doi.org/10.1021/ma061357b.

R Miyakoshi , A Yokoyama , T Yokozawa . . J Am Chem Soc , 2005 . 127 17542 - 17547 . DOI:10.1021/ja0556880http://doi.org/10.1021/ja0556880.

Z L Zhang , P Hu , X Li , H M Zhan , Y Z Cheng . . J Polym Sci,Part A:Polym Chem , 2015 . 53 1457 - 1463 . DOI:10.1002/pola.27577http://doi.org/10.1002/pola.27577.

C S Fischer , M C Baier , S Mecking . . J Am Chem Soc , 2013 . 135 1148 - 1154 . DOI:10.1021/ja311497ehttp://doi.org/10.1021/ja311497e.

E Elmalem , F Biedermann , K Johnson , R H Friend , W T S Huck . . J Am Chem Soc , 2012 . 134 17769 - 17777 . DOI:10.1021/ja3080677http://doi.org/10.1021/ja3080677.

W G Huang , L J Su , Z S Bo . . J Am Chem Soc , 2009 . 131 10348 - 10349 . DOI:10.1021/ja9033846http://doi.org/10.1021/ja9033846.

G L Tu , C Y Mei , Q G Zhou , Y X Cheng , Y H Geng , L X Wang . . Adv Funct Mater , 2006 . 16 101 - 106 . DOI:10.1002/(ISSN)1616-3028http://doi.org/10.1002/(ISSN)1616-3028.

L Chen , B H Zhang , Y X Cheng , Z Y Xie , L X Wang , X B Jing , F S Wang . . Adv Funct Mater , 2010 . 20 3143 - 3153 . DOI:10.1002/adfm.201000840http://doi.org/10.1002/adfm.201000840.

J Liu , Q Q Zhou , Y X Cheng , Y H Geng , L X Wang , D G Ma , X B Jing , F S Wang . . Adv Funct Mater , 2006 . 16 957 - 965 . DOI:10.1002/(ISSN)1616-3028http://doi.org/10.1002/(ISSN)1616-3028.

J Liu , Q Q Zhou , Y X Cheng , Y H Geng , L X Wang , D G Ma , X B Jing , F S Wang . . Adv Mater , 2005 . 17 2974 - 2978 . DOI:10.1002/(ISSN)1521-4095http://doi.org/10.1002/(ISSN)1521-4095.

J Liu , X Guo , L J Bu , Z Y Xie , Y X Cheng , Y H Geng , L X Wang , X B Jing , F S Wang . . Adv Funct Mater , 2007 . 17 1917 - 1925 . DOI:10.1002/(ISSN)1616-3028http://doi.org/10.1002/(ISSN)1616-3028.

J Liu , Y X Cheng , Z Y Xie , Y H Geng , L X Wang , X B Jing , F S Wang . . Adv Mater , 2008 . 20 1357 - 1362 . DOI:10.1002/(ISSN)1521-4095http://doi.org/10.1002/(ISSN)1521-4095.

H W Fu , Q L Song , J Li , Z L Zhang , X Li , H M Zhan , Y X Cheng . . J Coord Chem , 2014 . 67 482 - 494 . DOI:10.1080/00958972.2014.894993http://doi.org/10.1080/00958972.2014.894993.

H W Fu , J Li , Z L Zhang , H M Zhan , X Li , Y X Cheng . . J Org Chem , 2013 . 738 55 - 58 . DOI:10.1016/j.jorganchem.2013.04.016http://doi.org/10.1016/j.jorganchem.2013.04.016.

Z J Zhang , H K Tian , Q Liu , L X Wang , Y H Geng , F S Wang . . J Org Chem , 2006 . 71 4332 - 4335 . DOI:10.1021/jo0602470http://doi.org/10.1021/jo0602470.

S T Lin , Y C Tung , W C Chen . . J Mater Chem , 2008 . 18 3985 - 3992 . DOI:10.1039/b807118ghttp://doi.org/10.1039/b807118g.

K Matsubara , S Miyazaki , Y J Koga , Y Nibu , T Hashimura , T Matsumoto . . Organometallics , 2008 . 27 6020 - 6024 . DOI:10.1021/om800488xhttp://doi.org/10.1021/om800488x.

H H Zhang , C H Xing , Q S Hu . . J Am Chem Soc , 2012 . 134 13156 - 13159 . DOI:10.1021/ja302745thttp://doi.org/10.1021/ja302745t.

T Yokozawa , R Suzuki , M Nojima , Y Ohta , A Yokoyama . . Macromol Rapid Commun , 2011 . 32 801 - 806 . DOI:10.1002/marc.v32.11http://doi.org/10.1002/marc.v32.11.

T Forster . . Discuss Faraday Soc , 1959 . 27 7 - 17 . DOI:10.1039/DF9592700007http://doi.org/10.1039/DF9592700007.

C G Dong , Q S Hu . . J Am Chem Soc , 2005 . 127 10006 - 10007 . DOI:10.1021/ja052547phttp://doi.org/10.1021/ja052547p.

S K Weber , F Galbrecht , U Scherf . . Org Lett , 2006 . 8 4039 - 4041 . DOI:10.1021/ol061476bhttp://doi.org/10.1021/ol061476b.

S Diez-Gonzalez , N Marion , S P Nolan . . Chem Rev , 2009 . 109 3612 - 3676 . DOI:10.1021/cr900074mhttp://doi.org/10.1021/cr900074m.

H Jacobsen , A Correa , A Poater , C Costabile , L Cavallo . . Coord Chem Rev , 2009 . 253 687 - 703 . DOI:10.1016/j.ccr.2008.06.006http://doi.org/10.1016/j.ccr.2008.06.006.

更多指标>

Views

下载量

CSCD

Alert me when the article has been cited

提交

Tools

Publicity Resources

Synthesis and Luminescent Properties of Thermally Activated Delayed Fluorescence Conjugated Polymers with Carbazole/Acridine as Backbone Donor and Terpyridine as Pendant Acceptor

Photoluminescence and Luminescent Mechanism of Dextran

Preparation and Photoluminescent Properties of Polyimides Containing Triphenylamine Pendant Group

Recent Advances of Photoluminescence Polyimides

A Kind of Water-Soluble Polyfluorene Nanoparticles Prepared by Inclusion Complexation of -Cyclodextrin

Related Author

No data

Related Institution

State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences

School of Applied Chemistry and Engineering, University of Science and Technology of China

State Key Laboratory of Bio-Fibers and Eco-Textiles, College of Materials Science and Engineering, Qingdao University

College of Chemistry and Chemical Engineering, Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University

PCFM Lab, GD HPPC Lab, Guangdong Engineering Technology Research Center for High-performance Organic and Polymer Photoelectric Functional Films, School of Chemistry, Sun Yat-sen University

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