Materials 2011, 4(11), 1906-1926; doi:10.3390/ma4111906
Article

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

Yusuke Ishigaki 1 email, Takanori Suzuki 1,* email, Jun-ichi Nishida 1,† email, Aiichiro Nagaki 2 email, Naofumi Takabayashi 2 email, Hidetoshi Kawai 1,‡ email, Kenshu Fujiwara 1 email and Jun-ichi Yoshida 2 email
1 Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan 2 Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8530, Japan † Present address: Interdisciplinary School of Science and Engineering, Tokyo Institute of Technology, Yokohama 226-8502, Japan ‡ Present address: Department of Chemistry, Faculty of Science, Tokyo University of Science, Shinjuku 162-8601, Japan
* Author to whom correspondence should be addressed.
Received: 13 September 2011; in revised form: 6 October 2011 / Accepted: 10 October 2011 / Published: 26 October 2011
(This article belongs to the Special Issue Electrochromic Materials and Devices)
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Abstract: 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].
Keywords: electrochromism; organic dye; cationic dye; hysteresis; dynamic redox system; reaction integration; flow microreactor

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MDPI and ACS Style

Ishigaki, Y.; Suzuki, T.; Nishida, J.-I.; Nagaki, A.; Takabayashi, N.; Kawai, H.; Fujiwara, K.; Yoshida, J.-I. 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 2011, 4, 1906-1926.

AMA Style

Ishigaki Y, Suzuki T, Nishida J-I, Nagaki A, Takabayashi N, Kawai H, Fujiwara K, Yoshida J-I. 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. 2011; 4(11):1906-1926.

Chicago/Turabian Style

Ishigaki, Yusuke; Suzuki, Takanori; Nishida, Jun-ichi; Nagaki, Aiichiro; Takabayashi, Naofumi; Kawai, Hidetoshi; Fujiwara, Kenshu; Yoshida, Jun-ichi. 2011. "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 4, no. 11: 1906-1926.

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