Design and Synthesis of 9,9-Dioctyl-9H-Fluorene Based Electrochromic Polymers

作者:Jiang, Qinglin; Zhen, Shijie; Mo, Daize; Lin, Kaiwen; Ming, Shouli; Wang, Zhipeng; Liu, Congcong; Xu, Jingkun*; Yao, Yuanyuan; Duan, Xuemin; Zhu, Danhua; Shi, Hui
来源:Journal of Polymer Science Part A: Polymer Chemistry , 2016, 54(3): 325-334.
DOI:10.1002/pola.27935

摘要

Two novel heterocycle-fluorene-heterocycle monomers, 2,2'-(9,9-dioctyl-9H-fluorene-2,7-diyl) dithiophene (Th-F-Th) and 5,5'-(9,9-dioctyl-9H-fluorene-2,7-diyl)bis(2,3-dihydrothieno[3,4-b][1,4]dioxine) (EDOT-F-EDOT), were synthesized via Stille coupling reaction and electropolymerized to form corresponding polymers P(Th-F-Th) and P(EDOT-F-EDOT). Furthermore, the optoelectronic properties of the obtained monomers and polymers were explored using cyclic voltammetry (CV), UV-vis, and emission spectra and in situ spectroelectrochemical techniques. The band gap values of monomers calculated by DFT were 3.75 eV for EDOT-F-EDOT and 4.03 eV for Th-FTh, while that of P(EDOT-F-EDOT) and P(Th-F-Th) were brought down to 1.70 and 2.10 eV, respectively. Both polymers exhibited excellent redox activity and electrochromic performance. P(EDOT-F-EDOT) exhibited a maximum optical contrast of 25.8% at 500 nm in visible region with a response time of 1.2 s. In addition, the coloration efficiency of P(EDOT-F-EDOT) was calculated to be 220 cm(2) C-1.