TY - JOUR
T1 - Fused-Fluoran Leuco Dyes with Large Color-Change Derived from Two-Step Equilibrium
T2 - Iso-Aminobenzopyranoxanthenes
AU - Shirasaki, Yoshinao
AU - Okamoto, Yuta
AU - Muranaka, Atsuya
AU - Kamino, Shinichiro
AU - Sawada, Daisuke
AU - Hashizume, Daisuke
AU - Uchiyama, Masanobu
N1 - Funding Information:
This work was supported by JSPS KAKENHI (S) (No. 24229011), The Asahi Glass Foundation, Foundation NAGASE Science Technology Development, and Sumitomo Foundation (to M.U.).
PY - 2016/12/2
Y1 - 2016/12/2
N2 - Fluorans are popular leuco dyes that are used in various applications, such as carbonless-copy papers and thermal papers. Here, we describe unique leuco dyes in which two fluoran units are fused into a C2h structure (iso-aminobenzopyranoxanthenes; iso-ABPXs). iso-ABPXs exhibited a large two-step color change (colorless/pink and pink/blue-green) due to opening-closing of two spirolactone rings. The two-step equilibrium among the colorless, pink, and blue-green forms could be well controlled by adjusting acid concentration, solvent, and/or temperature.
AB - Fluorans are popular leuco dyes that are used in various applications, such as carbonless-copy papers and thermal papers. Here, we describe unique leuco dyes in which two fluoran units are fused into a C2h structure (iso-aminobenzopyranoxanthenes; iso-ABPXs). iso-ABPXs exhibited a large two-step color change (colorless/pink and pink/blue-green) due to opening-closing of two spirolactone rings. The two-step equilibrium among the colorless, pink, and blue-green forms could be well controlled by adjusting acid concentration, solvent, and/or temperature.
UR - http://www.scopus.com/inward/record.url?scp=85001086183&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85001086183&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.6b02403
DO - 10.1021/acs.joc.6b02403
M3 - Article
AN - SCOPUS:85001086183
VL - 81
SP - 12046
EP - 12051
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 23
ER -