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
;Kenshu Fujiwara;Hidetoshi Kawai;Aiichiro Nagaki;Naofumi Takabayashi;Takanori Suzuki;Jun-ichi Nishida;Yusuke Ishigaki;Jun-ichi Yoshida
Nature Materials2011Vol. 4pp. 1906-1926
191
fujiwara2011materialshysteretic
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].