• Title/Summary/Keyword: Squarylium

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Synthesis of Bis(dithiobenzil) Metal Complex and Its Photostability (Bis(dithiobenzil) 금속 화합물의 합성 및 광안정성)

  • Lee, Gun-Dae;Park, Na Yi;Jeon, Seung Yup;Heo, Jin;Son, Dae Hee;Hwang, Tae Kyung;Park, Seong Soo
    • Applied Chemistry for Engineering
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    • v.18 no.5
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    • pp.433-437
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    • 2007
  • Bis(dithiobenzil) metal complex, used as functional NIR absorbing dye and photostabilizer, was synthesized using bezoin and anisoin as intermediate compounds. And squarylium, a charge generation material, was synthesized to find its photostability effect. The structure of the product was determined by $^1H-NMR$ and FT-IR and the thermal property was analyzed by DSC and TGA. Optical property and photostability were determined by UV-Vis-NIR spectroscopy. High absorbance was obtained in the NIR range and maximum absorbing wavelength was shifted depending on the nature and position of substituent in the bis(dithiobenzil) metal complex. The photofading effect of squarylium decreased by the addition of bis(dithiobenzil) metal complex.

The Synthesis and Evaluation of Squarylium Dyes Based On the NIR Spectra Region

  • Park, Soo-Youl;Shin, Seung-Rim;Shin, Joung-Il;An, Kyoung-Lyong;Jun, Kun
    • Proceedings of the Korean Society of Dyers and Finishers Conference
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    • 2008.10a
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    • pp.131-132
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    • 2008
  • Several squarylium dyes, derived from benzothiazole and indoles, were synthesized as a potential NIR dyes with absorption in the 700-900 nm region. These chromophores were induced much more bathochromic shift in the absorption maximum of the compound relative to the neutral parent squarylium dyes which we were described before. The squaryliums offer a convenient way of linking the dye to functional substrates and may be an advantage to be potential chromophores for NIR-absorbing, NIR-Cut-off filter, PDT(Photo Dynamic Therapy) materials.

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Syntheses of Improved Polymer/Organic Materials for Electroluminescence(EL) Device and Electro-Optical Characteristics(Ⅱ) Properties of EL Device using Squarylium Dye as Emitting Material (고기능 EL소자용 고분자/유기 재료의 합성 및 전기 광학적 특성(Ⅱ) Squarylium 색소를 이용한 EL소자의 특성)

  • Kim, Sung Hoon;Bae, Jin Seok;Hwang, Seok Hwan;Park, Lee Soon
    • Journal of the Korean Chemical Society
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    • v.41 no.3
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    • pp.144-149
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    • 1997
  • Organic electroluminescence devices(ELD) were fabricated using by molecularly doped method with N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine(TPD) as a hole transport agent, squarylium dye as an emitting agent, and side chain liquid crystalline polymer(MCH) as matrix for TPD. An indium-tin-oxide(ITO) coated glass and an Mg electrode were used as the hole and the electron injecting electrode, respectively. The highest stability of ELD was obtained by spin coating method using dichloroethane as a solvent at a polymer/TPD concentration of 0.005 wt%. For the EL cell with ITO/polymer-TPD/SQ dye/Mg structure, we achieved light red luminescence at a current of 102 mA/$cm^2$ with an applied voltage of 23 V.

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Syntheses and Absorption Spectra of Polymethine Cyanine Dyes Such as Squarylium and Croconium Dyes (Squarylium, Croconium계 기능성 색소의 합성과 흡수 스펙트라)

  • 김성훈;한선경;임용진
    • Textile Coloration and Finishing
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    • v.6 no.1
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    • pp.28-32
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    • 1994
  • The synthesis and absorption spectra of squarvlium(SQ) dyes and croconium(CR) dyes were .studied. Absorption spectra of SQ dye in various solvents exhibited a negative solvatochrornism. Thus, it was suggested that the structure of SQ dye may be a highly polar structure. The λ$_{max}$ of CR dyes undergoes a bathochromic shift of about 100nm compared with the corresponding SQ dyes. This shift can be calculated by the Pariser-Parr-Pople molecular orbital method. From the PPP MO calculation results, we found that SQ dye and CR dye have a almost same Highest Occupied Molecular Orbital(HOMO) level(SQ : -8.0eV, CR : -8.09eV). On the other hand, energy levels of Lowest Unoccupied Molecular Orbital(LUMO) of SQ and CR dyes are -4.09eV and -4.13eV respectively. Thus, replacement of five membered ring by four membered ring in SQ dye causes a large bathochromic shift.t.

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Syntheses and Photostability of Unsymmetrical Squarylium Dyes for Organic Photoconductors(OPC) (유기광전도재료 (OPC)용 비대칭 Squarylium계 색소의 합성과 광안전성)

  • 김성훈
    • Journal of the Korean Graphic Arts Communication Society
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    • v.12 no.1
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    • pp.133-143
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    • 1994
  • A new photochromic spiroxazine dye having a pyridinium s-triazine moiety has been prepared. It shows a reversible photochemical color change from colorless to reddish-purple in ethanol solution. In ethanol solution the half life time of the open form was 150sec, which was shortened by raising temperature. Silica-immobilized spiroxazine(6). Fine power of silica-immobilized spiroxazine was changed intensely blue from colorless by U.V. light or sunlight.

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A Study on the Correlation between Anchor Point and printing quality in a Uncoated Paper (비도피지에서 투묘효과와 인쇄품질의 관계에 관한 연구)

  • 김애연
    • Journal of the Korean Graphic Arts Communication Society
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    • v.12 no.1
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    • pp.117-132
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    • 1994
  • New methodolgies for the syntheses of unsymmetrical squarylium(SQ) dyes for organic photoconductors(OPC) were developed and photostabilities for these dyes were dicucced. These dyes absorbed at 640-690nm and exhibit high molecular extinction coefficient about 10. photodegradation rate of these dyes is acceralated in the presence if singlet oxygen sensitizer. On the other hand, the photodegradation rate os retarded by adding effective singlet oxygen quencher, such as 2:1 metal dithiolate. It is suggested that the photodegration of unsymmetrical SQ dye may be due to a photo-oxidation involving singlet oxygen.

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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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