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Acta Phys. -Chim. Sin.  2017, Vol. 33 Issue (12): 2550-2558    DOI: 10.3866/PKU.WHXB201706071
ARTICLE     
Synthesis of Poly(bis-3, 4-ethylenedioxythiophene methine)s with Side-Chain Comprising Electro-Optical Moieties and Alkyl Chain Effect in Solid State Polymerization
Tong PEI,Kai PENG,Xin-Yi CAI,Liang-Jie YUAN*(),Jiang-Bin XIA*()
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Abstract  

New poly(bis-3, 4-ethylenedioxythiophene methine)s derivatives with typical electro-optical moieties of thiophene, carbazole and fluorene as the side chains are obtained by facile solid state polymerization (SSP) or melt state polymerization (MSP). Detail characterizations of these polymers are carried out and some key monomers' crystals are obtained for structures analysis. It is found that existence of alkyl chains decrease monomers onset temperatures for SSP (Tonset) due to the weakening of the intermolecular interaction in crystals.



Key wordsPoly (bis-3, 4-ethylenedioxythiophene methine) s derivatives      Solid and melt state polymerization      Alkyl chain effect     
Received: 08 May 2017      Published: 09 June 2017
MSC2000:  O646  
Fund:  the National Natural Science Foundation of China(21371138);the Funds for Creative Research Groups of Hubei Province, China(2014CFA007);the Fundamental Research Funds for the Central Universities, China(2042015kf0180)
Corresponding Authors: Liang-Jie YUAN,Jiang-Bin XIA     E-mail: jbxia@whu.edu.cn;ljyuan@whu.edu.cn
Cite this article:

Tong PEI,Kai PENG,Xin-Yi CAI,Liang-Jie YUAN,Jiang-Bin XIA. Synthesis of Poly(bis-3, 4-ethylenedioxythiophene methine)s with Side-Chain Comprising Electro-Optical Moieties and Alkyl Chain Effect in Solid State Polymerization. Acta Phys. -Chim. Sin., 2017, 33(12): 2550-2558.

URL:

http://www.whxb.pku.edu.cn/10.3866/PKU.WHXB201706071     OR     http://www.whxb.pku.edu.cn/Y2017/V33/I12/2550

 
 
 
 
Conversion for 24 h (temperature)Abs. λmax/nm solutionAbs.λedge/nm solutionEgapaHOMOb (eV)LUMOc (eV)
P(Th-EDOT)> 95 %, 110 ℃340, 357, 5757221.725.293.57
P(BuTh-EDOT)> 95 %, 130 ℃355, 389, 411, 4606661.864.933.07
P(Carb-EDOT)> 95 %, 150 ℃340, 612,7301.704.632.93
P(Flu-EDOT)> 95 %, 100 ℃342, 6407631.634.572.94
 
 
 
 
 
Distance/nm Angle/(°)
I1/I2 S1/S2 bridge length (C―CH(R)―C) ∠C―CH(R)―C ∠S1CH(R)S2 ∠I1CH(R)I2
I2-Th-EDOT 0.9229 0.3973 0.2526 113.50 88.91 103.12
I2-Flu-EDOT 0.9358 0.3979 0.2534 113.27 88.88 103.54
 
Molecules parametersI2-Th-EDOTI2-Flu-EDOT
shortest I/I distance/nm0.4397a0.5391a
2nd shortest I/I distance/nm0.44250.5650
3rd shortest I/I distance/nm0.61910.7893
C-C contact shortest distance/nm0.49100.5814
C-C contact 2nd shortest distance/nm0.52440.7932
longer than 2rw of iodineb9.9%34.8
Tonset of SSP (℃)6264
 
 
PolymersReaction conditionYield/%Mn/(g?mol-1) aPDIDPb
80 ℃ 3 d> 95 %10922.732
P(Flu-EDOT)90 ℃ 3 d> 95 %14561.323
150 ℃ 3 d> 95 %2101c1.884
P(Carb-C16-EDOT)100 ℃ 3 d> 95 %14971.692
150 ℃ 3 d> 95 %190591.0727
 
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