Synthesis of Poly(3-dodecyl-2,5-thienylene vinylene) by Solid-State Metathesis Polycondensation

被引:32
作者
Delgado, Paula A. [1 ]
Liu, David Y. [1 ]
Kean, Zachary [1 ]
Wagener, Kenneth B. [1 ]
机构
[1] Univ Florida, Dept Chem, George & Butler Polymer Res Lab, Gainesville, FL 32611 USA
关键词
ELECTROCHEMICAL PROPERTIES; POLYMERIZATION; CATALYSTS; POLYMERS;
D O I
10.1021/ma2020529
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
The synthesis of poly(thienylene vinylenes) (PTV) has been attracting attention due to the low band gaps and high electrical conductivities of these materials, making them applicable for charge storage devices, transparent conductive coatings, and electrochromic devices. Unsubstituted PTV is an intractable polymer that is usually synthesized via a processable precursor. This article reports the synthesis of conjugated polymers using solid-state metathesis conditions, demonstrating the efficiency of this methodology for preparation of a processable polymer, such a 3-dodecyl PTV (P3DDTV). The 3-dodecyl-2,5-dipropenylthiophene was synthesized and subsequently polymerized using ADMET conditions with Grubbs' second-generation catalyst. The prepolymer film (M-n = 4000 g/mol) was further polymerized in the solid state to give a final product with M-n = 14 000 g/mol (a 3.5-fold increase while in the solid state). The polymer obtained by this methodology exhibited thermal (T-g = 43 degrees C and T-m = 115 degrees C) and electrochemical (optical band gap of 1.65 eV and HOMO energy level of 5.35 eV) properties similar to those of PTV polymers synthesized by ADMET polymerization using a high boiling solvent or by cross-coupling reactions.
引用
收藏
页码:9529 / 9532
页数:4
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