Fused-Fluoran Leuco Dyes with Large Color-Change Derived from Two-Step Equilibrium: Iso-Aminobenzopyranoxanthenes

Yoshinao Shirasaki; Yuta Okamoto; Atsuya Muranaka; Shinichiro Kamino; Daisuke Sawada; Daisuke Hashizume; Masanobu Uchiyama

doi:10.1021/acs.joc.6b02403

Fused-Fluoran Leuco Dyes with Large Color-Change Derived from Two-Step Equilibrium: Iso-Aminobenzopyranoxanthenes

Yoshinao Shirasaki, Yuta Okamoto, Atsuya Muranaka, Shinichiro Kamino, Daisuke Sawada, Daisuke Hashizume, Masanobu Uchiyama

Research output: Contribution to journal › Article

14 Citations (Scopus)

Abstract

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 C_2h 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.

Original language	English
Pages (from-to)	12046-12051
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	81
Issue number	23
DOIs	https://doi.org/10.1021/acs.joc.6b02403
Publication status	Published - Dec 2 2016

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ASJC Scopus subject areas

Organic Chemistry

Cite this

Shirasaki, Y., Okamoto, Y., Muranaka, A., Kamino, S., Sawada, D., Hashizume, D., & Uchiyama, M. (2016). Fused-Fluoran Leuco Dyes with Large Color-Change Derived from Two-Step Equilibrium: Iso-Aminobenzopyranoxanthenes. Journal of Organic Chemistry, 81(23), 12046-12051. https://doi.org/10.1021/acs.joc.6b02403

Fused-Fluoran Leuco Dyes with Large Color-Change Derived from Two-Step Equilibrium : Iso-Aminobenzopyranoxanthenes. / Shirasaki, Yoshinao; Okamoto, Yuta; Muranaka, Atsuya; Kamino, Shinichiro; Sawada, Daisuke; Hashizume, Daisuke; Uchiyama, Masanobu.

In: Journal of Organic Chemistry, Vol. 81, No. 23, 02.12.2016, p. 12046-12051.

Research output: Contribution to journal › Article

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abstract = "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.",

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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.

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Access to Document

10.1021/acs.joc.6b02403