Synthesis of Small Band Gap Poly[Bis-EDOT-Isoindigo] via Direct Arylation and Oxidative Electropolymerization, and Its Optoelectronic Properties
Synthesis of Small Band Gap Poly[Bis-EDOT-Isoindigo] via Direct Arylation and Oxidative Electropolymerization, and Its Optoelectronic Properties
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DOI：
10.5796/electrochemistry.84.570
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发表时间：
2016-08
期刊：
影响因子：
2.5
通讯作者：
S. Hayashi;T. Koizumi
中科院分区：
文献类型：
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作者：
S. Hayashi;T. Koizumi
本文报道了氯化物促进的6，6 ′ -二溴- N，N ′ -（2-乙基己基）异靛（ID）与4.0当量的3，4-乙撑二氧噻吩（EDOT）的直接芳基化反应，得到了一种小带隙的给体-受体低聚物6，6 ′ -bisEDOT-N，N ′ -（2-乙基己基）异靛（BEDOTID），产率为97%。通过以下两种方法进行BEDOTID的聚合：（1）二氯甲烷中的电氧化（均偶联）反应和（2）氯仿中的Pd催化氧化（均偶联）反应。这些方法得到不溶性聚[双-EDOT-异靛蓝]，PBDOTID。用通过电氧化聚合制备的膜进行PBEDOT ID的表征，其基于给电子EDOT和接受电子的异靛蓝单元显示出低的光学和电化学带隙特性（分别为1.33和1.28eV）。扫描速率下的电流密度的测量证明艾德获得的PBEDOTID膜是均匀的。
We have demonstrated a chloride-promoted direct arylation of 6,6 ′ -dibromo- N , N ′ -(2-ethylhexyl)isoindigo, ID, with 4.0 equivalent of 3,4-ethylenedioxythiophene, EDOT, giving a small band gap donor-acceptor oligomer, 6,6 ′ -bisEDOT- N , N ′ -(2-ethylhexyl)isoindigo, BEDOTID in 97% yield. The polymerization of BEDOTID was performed by following two approaches; (1) electro-oxidative (homo-coupling) reaction in dichloromethane and (2) Pd-catalyzed oxidative (homo-coupling) reaction in chloroform. These approaches afforded insoluble poly[bis-EDOT-isoindigo], PBDOTID. Characterization of PBEDOTID was performed with the fi lm prepared by electro-oxidative polymerization, which showed low optical and electrochemical band gap properties (1.33 and 1.28eV, respectively) based on the electron-donating EDOT and electron-accepting isoindigo units. The measurement of the current density on scan rate justi fi ed that the obtained PBEDOTID fi lm was uniform.