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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

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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 electrochromism; organic dye; cationic dye; hysteresis; dynamic redox system; reaction integration; flow microreactor
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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