Hysteretic Tricolor Electrochromic Systems Based on the Dynamic Redox Properties of Unsymmetrically Substituted Dihydrophenanthrenes and Biphenyl-2,2'-Diyl Dications: Efficient Precursor Synthesis by a Flow Microreactor Method

Materials

Yusuke Ishigaki²  Takanori Suzuki²  Jun-ichi Nishida²  Aiichiro Nagaki¹  Naofumi Takabayashi¹  Hidetoshi Kawai²  Kenshu Fujiwara² 

[1] Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8530, Japan; E-Mails:;Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan; E-Mails:

关键词: electrochromism;    organic dye;    cationic dye;    hysteresis;    dynamic redox system;    reaction integration;    flow microreactor;   

DOI  :  10.3390/ma4111906

来源: mdpi

【 摘 要 】

A series of biphenyl-2,2'-diylbis(diarylmethanol)s 3, which have two kinds of aryl groups at the bay region, were efficiently obtained by integrated flow microreactor synthesis. The diols 3NO/NX are the precursors of unsymmetric biphenylic dications 2NO/NX²⁺, which are transformed into the corresponding dihydrophenanthrenes 1NO/NX via 2NO/NX^+• upon reduction, when they exhibit two-stage color changes. On the other hand, the steady-state concentration of the intermediate 2NO/NX^+• is negligible during the oxidation of 1NO/NX to 2NO/NX²⁺, which reflects unique tricolor electrochromicity with a hysteretic pattern of color change [color 1→color 2→color 3→color 1].

【 授权许可】

CC BY   
© 2011 by the authors; licensee MDPI, Basel, Switzerland.