Reversible coloring/decoloring reaction of leuco dye controlled by long-chain molecule

Horiguchi, Takashi; Koshiba, Yasuko; Ueda, Y.; Origuchi, Chikako; Tsutsui, Kyoji

doi:10.1016/j.tsf.2007.04.085

Cited by 38 publications

(33 citation statements)

References 11 publications

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“…1b). To our pleasant surprise, most of oxazolidines (1)(2)(3)(4)(5) and oxazines (11)(12) have favourable hydrochromic properties with good colour intensity and stability at ambient conditions, while the well-studied conventional spiropyrans (14-18) hardly show hydrochromism under the same conditions, and their OFs can only be observed either at elevated temperature or in the dark with poor colour intensity (more than one order of magnitude lower) (see Supplementary Fig. 1 and Supplementary Discussion).…”

Section: Resultsmentioning

confidence: 95%

“…We assumed that breaking the conjugated linkage of the zwitterions could improve their colour stability. In order to prove our assumption, we have designed and synthesized three classes of 18 structurally related switchable molecules-oxazolidines (1-10), oxazines (11)(12)(13) and spiropyrans (14)(15)(16)(17)(18) (Fig. 1a).…”

Section: Resultsmentioning

confidence: 96%

“…Incorporating switchable dyes in paper as an imaging layer represents an ideal economic approach towards rewritable paper. Leuco dyes 12,13 and photochromic compounds 14,15 have attracted much attention as new rewritable imaging dyes for rewritable paper. In particular, spiropyrans and related molecular switches, which are well known to undergo light-stimulated reversible isomerizations [16][17][18][19] between ring-closed forms (CFs) and ringopen forms (OFs) accompanied by significant colour changes, might be suitable candidates for the development of rewritable paper 20,21 .…”

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confidence: 99%

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Hydrochromic molecular switches for water-jet rewritable paper

et al. 2014

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The days of rewritable paper are coming, printers of the future will use water-jet paper. Although several kinds of rewritable paper have been reported, practical usage of them is rare. Herein, a new rewritable paper for ink-free printing is proposed and demonstrated successfully by using water as the sole trigger to switch hydrochromic dyes on solid media. Water-jet prints with various colours are achieved with a commercial desktop printer based on these hydrochromic rewritable papers. The prints can be erased and rewritten dozens of times with no significant loss in colour quality. This rewritable paper is promising in that it can serve an eco-friendly information display to meet the increasing global needs for environmental protection.

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Section: Resultsmentioning

confidence: 95%

Section: Resultsmentioning

confidence: 96%

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confidence: 99%

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Hydrochromic molecular switches for water-jet rewritable paper

et al. 2014

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“…[16][17][18][19] The discoloration characteristics depending on the concentration change of glucose were observed by using the indicator of Benedict's solution. As a method using small photodiode and color coordinates, the method presented in this study can determine the amount and color of the sample contained in the substance when color reaction occurs and estimate the concentration of glucose.…”

Section: Introductionmentioning

confidence: 99%

A study on detection of glucose concentration using changes in color coordinates

Kim

et al. 2016

Bioengineered

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Glucose concentration is closely related to the metabolic activity of cells and it is the most important substance as the energy source of a living body which plays an important role in the human body. This paper proposes an optical method that can measure the concentration of glucose. The change in glucose concentration was observed by using CIE diagram, and wavelength and purity values were detected. Also, even small changes in glucose concentration can be evaluated through mathematical modeling. This system is simple, economical, and capable of quantifying optical signals with numerical values for glucose sensing. This method can be applicable to the clinical field that examines diabetes mellitus or metabolic syndrome.

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“…[6][7][8] There have also been reports of thermal reversible color changes using protonation of fluoran dyes. [9][10][11] However, as for optical disks, high-contrast information in readout will be required for readout of the region beyond the diffraction limit such as near-field optics, and it is difficult to achieve fast readout because the reflectance differences are small when marks under 40 nm or multi-layer information for T bit recording are involved.…”

Section: Introductionmentioning

confidence: 99%

Investigation of Quenching Mechanism in Thermoreversible Fluorescent Recording Materials of Fluorescence Using Thermochromic Fluorescence Resonance Energy Transfer

Hirata

Vácha

Watanabe

2010

Jpn. J. Appl. Phys.

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We demonstrated reversible thermosensitive recording of a fluorescent image (TRF) using a low-molecular-weight mixture consisting of a fluorescent dye, a fluoran dye, a developer, and a reversible matrix. In this material, reversible thermoresponsive disorder-crystal transition triggers a cyclical colorless-color change of a fluoran dye, which induces on-off switching of fluorescence resonance energy transfer (FRET) from a fluorescent dye to a fluoran dye. On-off switching of fluorescence is induced by heat-promoted off-on switching of FRET. Modulation of fluorescence is held at room temperature by utilizing thermal hysteresis, and nondestructive readout of the fluorescent image is accomplished in the presence of excitation light. Here, we investigate the on-off switching mechanism of fluorescence in this recording material. We analyzed the theoretical factor of emission quenching in the erasing state by comparing the theoretical overlap integral between fluorescent dyes and fluoran dyes on the basis of the FRET theory with experimental emission contrast for various combinations of fluorescent dyes and fluoran dyes. It was proved that fluorescence on-off switching occurs mainly by concentration quenching due to the aggregation of fluorescent dyes and FRET from isolated fluorescent dyes to colored fluoran dyes. The key issue to obtain both high-contrast fluorescence and high fluorescence quantum yield is to control these two factors. # Concentration quenching : Crystalline matrix M M M M M M Fig. 1. (Color online) Mechanism of thermoreversible on-off recording of fluorescence and nondestructive readout of fluorescent information.

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Reversible coloring/decoloring reaction of leuco dye controlled by long-chain molecule

Cited by 38 publications

References 11 publications

Hydrochromic molecular switches for water-jet rewritable paper

Hydrochromic molecular switches for water-jet rewritable paper

A study on detection of glucose concentration using changes in color coordinates

Investigation of Quenching Mechanism in Thermoreversible Fluorescent Recording Materials of Fluorescence Using Thermochromic Fluorescence Resonance Energy Transfer

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