Synthesis and Photoluminescene of Sulfonated Polyfluorenes Containing 9,9-bis(3-propylamide-2-methylpropane sulfonic acid) Fluorene

YAO Yao; GAO Shan; XU Yan-ming; FAN Xiao-xing; LI Jian; REN Qiang; WANG Chen-yi

doi:10.3788/fgxb20143512.1487

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Synthesis and Photoluminescene of Sulfonated Polyfluorenes Containing 9,9-bis(3-propylamide-2-methylpropane sulfonic acid) Fluorene

更新时间：2020-08-12

- Synthesis and Photoluminescene of Sulfonated Polyfluorenes Containing 9,9-bis(3-propylamide-2-methylpropane sulfonic acid) Fluorene
- Chinese Journal of Luminescence Vol. 35, Issue 12, Pages: 1487-1494(2014)
- 作者机构：
  
  常州大学材料科学与工程学院, 江苏常州 213164
- 作者简介：
- 基金信息：
- DOI：10.3788/fgxb20143512.1487
  CLC： O631.3;O641.4
- Received：28 July 2014，
  
  Revised：04 September 2014，
  
  Published：03 December 2014
- 稿件说明：
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姚尧, 高山, 徐延明等. 9,9-二-(3-丙基酰胺-2-甲基丙磺酸)芴共聚物的合成及荧光发光性能[J]. 发光学报, 2014,35(12): 1487-1494

YAO Yao, GAO Shan, XU Yan-ming etc. Synthesis and Photoluminescene of Sulfonated Polyfluorenes Containing 9,9-bis(3-propylamide-2-methylpropane sulfonic acid) Fluorene[J]. Chinese Journal of Luminescence, 2014,35(12): 1487-1494
姚尧, 高山, 徐延明等. 9,9-二-(3-丙基酰胺-2-甲基丙磺酸)芴共聚物的合成及荧光发光性能[J]. 发光学报, 2014,35(12): 1487-1494 DOI： 10.3788/fgxb20143512.1487.

YAO Yao, GAO Shan, XU Yan-ming etc. Synthesis and Photoluminescene of Sulfonated Polyfluorenes Containing 9,9-bis(3-propylamide-2-methylpropane sulfonic acid) Fluorene[J]. Chinese Journal of Luminescence, 2014,35(12): 1487-1494 DOI： 10.3788/fgxb20143512.1487.

摘要

利用迈克尔加成反应合成了2

7-二溴-9

9-二-(3-丙基酰胺-2-甲基丙磺酸)芴(FSO

并通过Suzuki偶合反应制备了9

9-二-(3-丙基酰胺-2-甲基丙磺酸)芴-9

9-二己基芴共聚物(PF6SO

H)和9

9-二-(3-丙基酰胺-2-甲基丙磺酸)芴-4

4'-联苯共聚物(PFDBSO

H).通过核磁共振氢谱(

H NMR)、凝胶渗透色谱(GPC)、紫外-可见吸收光谱对聚合物的结构进行了表征

利用荧光发射光谱对聚合物在各种条件下的荧光发光性能进行了研究.结果表明

上述两种磺酸型聚芴已被成功合成

这些聚合物具有较高的分子量并能够很好地溶于甲醇和水/醇混合溶剂中.荧光发光光谱研究表明:溶剂的极性、溶液的浓度和pH值、溶液中的金属离子都对磺酸型聚芴的发光性能有很大的影响.荧光发射光谱随着溶剂极性的增加逐渐红移.荧光强度随着溶液浓度的增加先增加后降低.当溶液pH从1增加到7.5时

荧光强度逐渐增加;当pH从7.5增加到12.5时

荧光强度降低直至猝灭.离子猝灭剂Mv

、Ag

、K

、Na

和Li

等对两种聚合物具有明显的猝灭效应

且对PF6SO

H的猝灭效应比对PFDBSO

H更强

这与磺酸型聚芴分子的刚性及离子的相互作用有关.

Abstract

7-dibromo-9

9-bis(3-propylamide-2-methylpropane sulfonic acid) fluorene (FSO

H) was synthesized by Michael addition reaction. Then

sulfonated polyfluorenes

poly[9

9-bis(3-propylamide-2-methylpropane sulfonic acid) fluorene] -

alt

-poly(9

9-dihexyl-fluorene) (PF6SO

H) and poly[9

9-bis(3-propylamide-2-methyl propane sulfonic acid) fluorene]-

alt

-poly(4

4'-diphenyl) (PFDBSO

H) were synthesized by Suzuki Coupling. The structure and properties of sulfonated polyfluorenes were investigated by

H NMR

gel permeation chromatography (GPC) and UV-visible absorption spectroscopy. Photoluminescence performances of polyfluorenes under various conditions were studied. The results show that these copolymers have high molecular weights and can dissolve in methanol and water/methanol mixture. The photoluminescent wavelengths of the sulfonated polyfluorenes are red shifted with the increasing of polarity of the solvents. The fluorescence intensity of the polyfluorenes increases with the increasing of the polyfluorenes concentration under low concentration. Under high concentration

the quenching effect can be observed. A gradually increasing trend of fluorescence intensity is found when pH varied from 1 to 7.5

and a reduction in fluorescence intensity even completely quenching is observed when the pH changed from 7.5 to 12.5. Ions

such as Mv

and Li

have quenching effects on the fluorescence of polyfluorenes. The quenching effect of metal ions on PF6SO

H shows much stronger than on PFDBSO

H because of the more rigid backbone of PF6SO

H and the interaction between the polymer and the ions.

关键词

Keywords

references

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