New fluoran leuco dyes having a phenylenediamine moiety at the 6-position of the xanthene ring

Yanagita, Mitsuhiro; Aoki, Izuo; Tokita, Sumio

doi:10.1016/s0143-7208(96)00129-5

Cited by 7 publications

(2 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The reaction can be reversible or irreversible ( Figure 1 A). Fluorans can therefore be considered functional compounds that can be used in thermo-, pH−, or pressure-sensitive recording systems [ 10 , 20 , 44 , 45 , 46 ]. The main two groups of leuco dyes based on fluoran skeletons possess different groups attached in position 6′ or positions 3′ and 6′ ( Figure 1 B).…”

Section: Introductionmentioning

confidence: 99%

Controlled Synthesis of Luminescent Xanthene Dyes and Use of Ionic Liquid in Thermochromic Reaction

2022

View full text Add to dashboard Cite

In this study, we demonstrate six novel xanthene derivatives and their spectroscopic and chemical properties. The presented synthesis examination allowed us to obtain two different compounds during one step, with open and closed lactone rings substituted with different length alkyl chains. Increasing the reaction efficiency to 77% was obtained using the microwave-assisted method. Moreover, the modification of O-alkylation synthesis in an ecofriendly way using a ball mill led to achieving exclusively one opened ring product. All of the synthesized compounds showed different spectroscopic behaviors in comparison with the different organic dyes; the typical concentration quenching of luminescence was not observed. The relationship between the length of the alkyl chain and the time of luminescence decay is presented. Synthetized closed forms of dyes turned out to be promising leuco dyes. For the first time, an ionic liquid was used as a developer of synthesized xanthene derivatives (as leuco dyes), which led to obtaining an irreversible thermochromic marker.

show abstract

Section: Introductionmentioning

confidence: 99%

Controlled Synthesis of Luminescent Xanthene Dyes and Use of Ionic Liquid in Thermochromic Reaction

2022

View full text Add to dashboard Cite

show abstract

“…Fluoran leuco dyes are well-known chromogenic compounds used as color formers for pressure and thermosensitive data-recording systems. Fluoran leuco dyes have been used as thermochromic materials in a mixture consisting of two materials: a color former (fluoran leuco dyes) and a color developer (proton donor). − In the presence of protons, the colorless leuco form in the fluoran leuco dye undergoes a ring-opening reaction to form the corresponding highly colored zwitterionic dye form. − Furthermore, the zwitterionic dye forms are thermally stable in a partially protic microenvironment at lower temperatures and in the solid phase, but the records on media slowly fade over the years …”

Section: Introductionmentioning

confidence: 99%

Leuco-Based Composite Resin Dosimeter Film

et al. 2019

View full text Add to dashboard Cite

A polystyrene (PS)-based composite resin dosimeter (CRD) film comprising 2-(phenylamino)-6-(dipentylamino)-3-methylspiro[9 H -xanthene-9,3′-phthalide] (Black305) fluoran leuco dye, cerium-doped yttrium aluminum perovskite YAlO 3 :Ce (YAP:Ce) scintillator, and 2-(4-methoxystyryl)-4,6-bis(trichloromethyl)-1,3,5-triazine (MBTT) photoacid generator was developed for the visualization of X-ray exposure doses in the range of 18–170 Gy. The color of the CRD film changed from yellow to black within this range based on the X-ray exposure dose. A CRD film based on Black305/YAP:Ce/MBTT/PS could be used to produce a dosimeter with various color change sensitivities by controlling the thermodynamic parameters of the constituent materials. A CRD film is a promising tool for measuring the X-ray exposure dose and can be used as an alternative to the existing radiochromic dosimeters.

show abstract