• Title/Summary/Keyword: leuco dyes

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The Synthesis of New Leuco Squarylium Dyes

  • Park, Soo-Youl;Jun, Kun;Shin, Seung-Rim;Shin, Jong-Il
    • Textile Coloration and Finishing
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    • v.19 no.5
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    • pp.24-29
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    • 2007
  • It is well known that certain classes of dye are reducible to stable colorless leuco compounds, which can be oxidized in air back to the colored species. We now reported that bis(4-dialkylaminophenyl)squaraine dyes are readily reduced in solution by borohydride to give alkali soluble leuco compound, which exists in the 3-hydroxy 2,4-bis(4-dialkylaminophenyl)cyclobuten-one. New alkylamine leuco compounds were synthesized by the reaction of leuco chloro-squaraine with alkylamine derivatives. The leuco compounds are easily isolated and can be air oxidized back to the squaraine dyes. These dyes have many technical application. e.g. in xerography, solar cell, optical recording material, redox indicators, and enzyme assays.

X-ray Crystal Structure of Hetaryl Leuco-TAM Dyes, (2Z,2'E)-2,2'-(2-Phenyl Propane-1,3-diylidene) Bis(1,3,3-trimethyl indoline) Derivatives

  • Keum, Sam-Rok;Roh, Se-Jung;Kim, Young-Nan;Im, Do-Hyuck;Ma, So-Young
    • Bulletin of the Korean Chemical Society
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    • v.30 no.11
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    • pp.2608-2612
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    • 2009
  • The unequivocal solid-state structure and stereochemistry of the hetaryl leuco-TAM dye, 2,2’-(2-phenyl propane- 1,3-diylidene) bis(1,3,3- trimethylindoline) derivatives were established using X-ray single crystal analysis. The X-ray crystal analysis showed that the (Z, E)-isomers only formed stereoselectively, with a so-called “threebladed propeller” conformation, from the reaction of a Fischer base and benzaldehyde derivatives. These isomers were stacked in a juxtaposition to form a dimer or a double dimer, adopting either a triclinic, with P-1, or monoclinic crystal system with a space group P21/n in the unit cell of the crystal.

Color Change Redox Behavior of the 1,3-Squaraine Dyes

  • Jun, Kun;Shin, Seung-Rim;Shin, Jong-Il;Park, Soo-Youl
    • Textile Coloration and Finishing
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    • v.18 no.5 s.90
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    • pp.53-60
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    • 2006
  • The 1,3-bis(4-aminoaryl)squaraines showed color, change behavior, they were found to undergo reduction with sodium borohydride in solution to give colorless leuco compounds, which oxidized readily in air back to the colored squaraine dye. We have shown that initial observations indicated that the derivatives synthesized gave new donor-acceptor chromophores. It is also interesting to note than the oxidation of the leuco squaraines did initially produce a species absorbing about 630-680 wavelengths. The 1,3-squaraines have found many uses as near-infrared absorbers, laser dyes and photoconductive materials. Furthermore their color-change redox behavior has potential in the area of peroxidase-based bioassaysas oxidation sensitive indicator systems were investigated.

Hyperbranched Poly(aryl ester)s as Developer Materials for Thermal Printing System

  • Jang, Yeon-Im;Choi, Won-Ho;An, Byeong-Kwan
    • Bulletin of the Korean Chemical Society
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    • v.34 no.4
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    • pp.1225-1231
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    • 2013
  • A novel class of hyperbranched polyesters, HPpEP and HPmEP, were prepared via a facile one-pot polymerization of a phloroglucinol (as a $B_3$ monomer) with a phthaloyl dichloride (as an $A_2$ monomer) for replacing a problematic BPA developer in thermal printing system. The resulting polymers, HPpEP and HPmEP, had highly branched structures and met well the requirements for high performance developer materials such as colorlessness, easy and inexpensive synthesis, high thermal stability, etc. In addition, these polymers exhibited an efficient reaction with leuco dyes (ODB-2) for a coloring process by releasing protons from linear and terminal phenol groups of polymers when heated.

New Synthetic Approach to Squarylium Near Infrared Dyes

  • Park, Soo-Youl;Oh, Sea-Wha
    • Proceedings of the Korean Society of Dyers and Finishers Conference
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    • 2003.04a
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    • pp.29-31
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    • 2003
  • The 1,3-bis(4-aminoaryl)squaraines showed colour change behaviour, they were found to undergo reduction with sodium borohydride in solution to give colourless leuco compounds, which oxidised readily in air back to the coloured squaraine dye. We have shown that oxidation of the parent leuco-squaraines gives the neutral squaraine system. Initial observations indicated that the derivatives gave new long-wavelength absorbing chromophores, and It is interesting to note that the onidation of the leuco squaraines did initially produce a species absorbing at longer wavelengths than the parent squaraine dye. This colour-change redox behaviour has potential in the area of peroxidase-based bioassays and artificial camouflage.

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Dye-sensitized Solar Cells Based on Fluoran Leuco Sensitizers (플루오란 로이코 염료를 이용한 염료감응형 태양전지)

  • Jung, Hye-In;An, Byeong-Kwan
    • Journal of the Korean Institute of Electrical and Electronic Material Engineers
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    • v.26 no.3
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    • pp.240-245
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    • 2013
  • The utilization of a fluoran leuco sensitizer, 2-anilino-6-dibutyl amino-3-methylfluoran (ODB-2), for dye-sensitized solar cells (DSSCs) was investigated through the examination of the adsorption of ODB-2 molecules onto the surfaces of porous titanium dioxide (titania, $TiO_2$) films and the photovoltaic properties of ODB-2-based DSSCs. Despite of the absence of the specific anchoring groups with titania, ODB-2 dye molecules were spontaneously adsorbed onto the titania surfaces because the lactone ring in ODB-2 was opened and changed into the carboxylic acid (-COOH) by releasing protons from the surfaces ($TiOH_2{^+}$) of titania, which consequently leads to the chemisorption reaction of ODB-2 molecules to the active sites of titania. DSSCs based on ODB-2 exhibited typical photovoltaic properties with an open-circuit voltage ($V_{OC}$) of 0.19 V, a short-circuit current ($J_{SC}$) of $0.30\;mA{\cdot}cm^{-2}$, a fill factor (FF) of 37%, and a conversion efficiency (PCE) of 0.02%.

An Approach to the Influence of Particle Size Distribution of Leuco Vat Dye Converted by a Reducing Agent

  • Shim Woo-Sub;Lee Jung-Jin;Shamey Renzo
    • Fibers and Polymers
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    • v.7 no.2
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    • pp.164-168
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    • 2006
  • Three vat dyes have been applied to regular viscose rayon and their dyeing and wash fastness properties were evaluated. Particle size determination was undertaken to obtain information about the size of dye particles converted by a reducing agent, to see if dye particle size has an affect on dyeing properties of regular viscose rayon. It is observed that viscose rayon exhibits more dyeability with reducing agent concentrations between 5-7.5 g/l. Also, we found that the vat dyeing system is greatly affected by the particle size of the vat dye converted to leuco form by a reducing agent.

Analysis of Physical Properties for Various Compositions of Reusable LMG and LCV Micelle Gel

  • Kang, Jin Mook;Lee, Dong Han;Cho, Yu Ra;Hwang, Seon Bung;Ji, Young Hoon;Ahn, So Hyun;Keum, Ki Chang;Lee, Re Na;Cho, Sam Ju;Noh, Insup
    • Progress in Medical Physics
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    • v.27 no.4
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    • pp.175-179
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    • 2016
  • In this study, we evaluated the reusable leuco malachite green (LMG) micelle gel properties dependent on various components of chemical concentration and compared with leuco crystal violet (LCV). The gels were delivered to 10, 20, 30, 40 and 50 Gy at 6 MV photon beam from linear accelerator and analyzed using spectrophotometry. We confirmed that the reusable LMG and LVC absorbance wavelength peak were made up at 630 nm and 600 nm respectively. The transparency of reusable LMG decreased with higher amount of trichloroacetic acid (TCAA) and lower reusable LMG dyes. 1 mM reusable LMG was the lowest transparency. The sensitivity was increased depending on lower trichloroacetic acid (TCAA) concentrations and the amount of suitable surfactant (Triton X-100), which was found to be 7 mM. However, we were not able to investigate sensitivity effects factor from reusable LMG dyes. The gel dosimeter containing 16 mM TCAA, 7 mM Triton X-100 gel dosimeter showed the highest sensitivity at $0.0021{\pm}0.0001cm^{-1}.Gy^{-1}$. The sensitivity of LCV was found to be higher than reusable LMG at $0.0037{\pm}0.0005cm^{-1}.Gy^{-1}$. The reusable LMG and LCV dose responses were shown to be $R^2=0.997$, $R^2=0.999$ respectively, as stable measurement results. Future research is necessary to improve dose sensitivity, dose rate dependency and gel fading with extensive chemical formulations.

Synthesis of Novel Morpholine Appended Crystal violet lactone Derivatives and an Investigation of Their Thermochromic Behavior

  • Kim, Myeong Jin;Muthukumar, Palanisamy;Angupillai, Satheshkumar;Son, Young-A
    • Textile Coloration and Finishing
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    • v.30 no.1
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    • pp.1-8
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    • 2018
  • In the present study, three morpholine substituted crystal violet lactone (CVL) have been synthesized to monitor the thermochromic property. This work is explaining the role of substituent on the lactone ring. The methyl substituents induced greater chromic effects than the chloro substituents. Furthermore, the three-component mixtures that contained CVL, bisphenol-A, and methyl stearate were used to analyse the thermochromic effect of the CVLs as bulk samples with various temperature. The thermochromic properties of the CVLs were evaluated using solid-state UV-Vis and FT-IR spectroscopic techniques. Finally, one of the synthesized CVL has been successfully converted into the form of a test paper similar to pH paper for use as thermal indicators.