Citation: DAI Yu-Yu, LI Wei-Jun, YAN Shuan-Ma, WANG Shi-Zhao, YU Yue, OUYANG Mi, CHEN Li-Tao, ZHANG Cheng. Dithenylpyrrole Structure Bridged with Phenyl or Biphenyl Rings:Molecular Configuration and Electrochromic Properties[J]. Acta Physico-Chimica Sinica, ;2017, 33(11): 2268-2276. doi: 10.3866/PKU.WHXB201705252 shu

Dithenylpyrrole Structure Bridged with Phenyl or Biphenyl Rings:Molecular Configuration and Electrochromic Properties

State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, College of Chemical Engineering, Zhejiang University of Technology, International Science & Technology Cooperation Base of Energy Materials and Application, Hangzhou 310014, P. R. China

Received Date: 30 March 2017
Revised Date: 11 May 2017

Fund Project: The project was supported by the National Natural Science Foundation of China (51603185, 51673174, 51573165, 51273179), Zhejiang Provincial Natural Science Foundation, China (LY17E030001, LY15E030006, LY12B03008), and Special Fund for Scientific Research from Zhejiang University of Technology, China (3817101101T).

A series of multi-branched dithienylpyrrole (SNS) monomers with rigid phenyl (PhSNS) and biphenyl rings (BPhSNS) as bridges were designed and synthesized, and were fabricated to form cross-linked polymers (pPhSNS, pBPhSNS) by electrochemical polymerization. Cyclic voltammetry (CV) results showed that PhSNS and BPhSNS exhibited similar oxidative properties except for one new higher-potential oxidative peak appearing in the curves of PhSNS. Theoretical calculations indicated that it should be attributed to the different steric configuration between the two dithienylpyrrole (SNS) units in PhSNS. One SNS unit possessed a larger twist angle (40.2°) between thiophene and pyrrole rings than the other one (21.2°), which indicated that PhSNS possessed a relatively larger energy gap (~0.4 eV) between HOMO-1 and HOMO than BPhSNS, for which HOMO and HOMO-1 levels were of almost the same energy. However, both PhSNS and BPhSNS showed similar onset oxidation potentials. The CV curves of pPhSNS and pBPhSNS showed that they presented similar oxidative properties, which enabled their corresponding electrochemical polymers to exhibit similar electrochromic properties. The UV-vis spectra of the corresponding polymers showed that both pPhSNS and pBPhSNS possessed similar optical absorption and similar multicolor switching between yellow (-0.8 V), greyish-green (0.9 V) and gray (1.1 V) colors. Besides, pPhSNS and pBPhSNS showed fast switching times of 0.57 s and 0.93 s at 1100 nm, respectively and reasonable contrasts of 46% and 31% at 1100 nm, respectively. These investigations may help understand the relationship between structural configuration and the electrochemistry/electrochromic properties for polymer electrochromic (PEC) materials research.
- Dithienylpyrrole,
- Molecular configuration,
- Theoretical calculation,
- Electorpolymerization,
- Electrochromic
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