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Development and Application of Functional Near Infrared Dyes

Research Project

Project/Area Number 62470035
Research Category

Grant-in-Aid for General Scientific Research (B)

Allocation TypeSingle-year Grants
Research Field 分析・地球化学
Research InstitutionNagasaki University

Principal Investigator

AKIYAMA Shuzo  Nagasaki University, School of Pharmaceutical Sciences, Professor, 薬学部, 教授 (50028148)

Co-Investigator(Kenkyū-buntansha) NAKATSUJI Shin'ichi  Nagasaki University School of Pharmaceutical Sciences, Associate Professor, 薬学部, 助教授 (90124833)
NAKASHIMA Kenichiro  Nagasaki University, School of Pharmaceutical Sciences, Associate Professor, 薬学部, 助教授 (30039656)
Project Period (FY) 1987 – 1989
Project Status Completed (Fiscal Year 1989)
Budget Amount *help
¥5,900,000 (Direct Cost: ¥5,900,000)
Fiscal Year 1989: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 1988: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1987: ¥4,000,000 (Direct Cost: ¥4,000,000)
KeywordsNear-infrared dye / Dye ethynolog / Functional dye / Infrared absorption / Non-linear optics material / Absorption spectra / PPP-MO / Butadiene / トリフェニルメタン系色素 / 近赤外吸収スペクトル / 色素アセチレン類似体 / トリフェニルメタン系色素エチノローグ
Research Abstract

1. It was found that the dye ethynologs containing xanthenylium, thioxanthenylium, or selenoxanthenylium system have been synthesized and these dyes have absorptions in the near-infrared (near-IR) region.
2. The dye ethynovinylogs derived from three substituted 1-penten-4-in-3-ols have been prepared and their spectral properties were examined to show absorptions in the near-IR.
3. Acetylenic analogs 3, 6-bis (dimethylamino) fluorenylium dyes, which absorb near-IR light (up to 1056nm in CH_2 Cl_2), have been prepared. The effects on the absorption maxima by substituents were fully examined. Although the chromophore systems of these dyes are not large, their spectral features are remarkable.
The characteristically large bathochromic shifts of the absorption bands into near-IR region by ring closure of the omicron- and omicron'-positions of the diphenylmethane units could hardly ascribed to increase of planarity. The antiaromatic or/and diradicaloid nature of the central cyclopentadienyl unit will play a significant role in conjugation.
4. A simple and convenient method was newly developed to afford aryl-substituted push-pull butadienes, i.e. a class of merocyanine dyes from 1,1-diaryl-2-propyn- 1-OIS. The scope of the reaction applying for several substrates was examined in detail. These dyes are excected for non-linear optics materials.
5. Various functional characters of the triphenylmethane dye ethynologs prepared are fully examined.
6. Their characteristic absorption properties were discussed on the basis of PPP-CI-MO calculations.

Report

(4 results)
  • 1989 Annual Research Report   Final Research Report Summary
  • 1988 Annual Research Report
  • 1987 Annual Research Report
  • Research Products

    (27 results)

All Other

All Publications (27 results)

  • [Publications] Shuzo Akiyama: "Triphenylmethane Dye Ethynologues with Absorption Bands in the Near I.R." J.Chem.Soc.,Chem.Commun.1987. 710-711 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Shuzo Akiyama: "Triphenylmethane Dye Ethynologues with Absorption Bands in the Near Infrared" J.Chem.Soc.,Perkin Trans.I. 1988. 3155-3161 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Shuzo Akiyama: "Diphenylmethane and Triphenylmethane Dye Ethynologues with Absorption Bands in the Near-Infrared" Dyes and Pigments. 9. 459-466 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Shin´ichi Nakatsuji: "A Simple and Convenient Synthesis of Aryl-Substituted Push-Pull Butadienes from 1,1-Diaryl-2-propyn-1-ols" Bull.Chem.Soc.Jpn.61. 2253-2255 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Shin´ichi Nakatsuji: "Synthesis and Absorption Spectral Properties of New Merocyanine Dye Systems Derived from Michler´s Ketone and 3,6-Bis(N,N-dimethylamino)fluorenone" Chem.Express. 4. 601-604 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Shin´ichi Nakatsuji: "3,6-Bis(dimethylamino)fluorenylium Dye Ethynologues:New Highly Coloured π-Electron System" J.Chem.Soc.,Chem.Commun.(inpress). 1990. (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Shin´ichi Nakatsuji: "Chemistry of Functional Dyes,ed.by z.Yoshida and T.Kitao;Synthesis of Merocyanine Dyes from 1,1-Diaryl-2-propyn-1-ol Systems" Mita press,Tokyo, 4 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] S. Akiyama: "Triphenylmethane Dye Ethynologues with Absorption Bands in the Near I.R." J. Chem. Soc., Chem. Commun., 1987, 710-711 (1987).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] S. Akiyama: "Triphenylmethane Dye Ethynologues with in the Near Infrared" J. Chem. Soc., Perkin Trans. I, 1988, 3155-3161 (1988).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] S. Akiyama: "Diphenylmethane and Triphenylmethane Dye Ethynologues with Absorption Bands in the Near-Infrared" Dyes and Pigments, 9, 459-466 (1988).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] S. Nakatsuji: "A Simple and Convenient Synthesis of Aryl-Substituted Push-Pull Butadienes from 1, 1-Diaryl-2-propyn-1-ols" Bull. Chem. Soc. Jpn. 61, 2253-2255 (1988).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] S. Nakatsuji: "Synthesis and Absorption Spectral Properties of New Merocyanine Dye Systems Derived from Michler's Ketone and 3,6-Bis(N,N-dimethylamino)fluorenone" Chem. Express, 4, 601-604 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] S. Nakatsuji: "3,6-Bis(dimethylamino)fluorenylium Dye Ethynologues: New Highly Colored pi-Electron System" J. Chem. Soc., Chem. Commun., 1990, (1990).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] S. Nakatsuji: "Chemistry of Functional Dyes, ed. by Z. Yoshida and T. Kitao; Synthesis of Merocyanine Dyes from 1,1-Diaryl-2-propyn-1-ol Systems" Mita Press, Tokyo Chapter 3, 63-66 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Shin'ichi Nakatsuji: "Synthesis and Absorption Spectral properties of New Merocyanine Dye Systems Derived from Michler's Ketone and 3,6-Bis(N,N-dimethylamino)fluorenone" Chem.Express. 4. 601-604 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Shin'ichi Nakatsuji: "3,6-Bis(dimethylamino)fluorenylium Dye Ethynologues:New Highly Coloured π-Electron System" J.Chem.Soc.,Chem.Commun. (1990)

    • Related Report
      1989 Annual Research Report
  • [Publications] Shin'ichi Nakatsuji: "Chemistry of Functional Dyes,ed.by Z.Yoshida and T.Kitao;Synthesis of Merocyanine Dyes from 1,1-Diaryl-2-propyn-1-ol Systems" Mita Press,Tokyo,

    • Related Report
      1989 Annual Research Report
  • [Publications] Akiyama,Shuzo: J.Chem.Soc.,Chem.Commun.710-711 (1987)

    • Related Report
      1988 Annual Research Report
  • [Publications] Akiyama,Shuzo: Dyes and Pigments. 8. 459-463 (1987)

    • Related Report
      1988 Annual Research Report
  • [Publications] Akiyama,Shuzo: Dyes and Pigments. 9. 459-466 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Akiyama,Shuzo: J.Chem.Soc.,Perkin I. 3155-3161 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Nakatsuji,Shin ichi: Bull.Chem.Soc.Jpn.61. 2253-2255 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Akiyama,Shuzo: J.Chem.Soc.,Perkin I.

    • Related Report
      1988 Annual Research Report
  • [Publications] Akiyama,Shuzo: J.Chem.Soc.,Chem.Commun.710-711 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] Akiyama,Shuzo: Dyes and Pigments. 8. 459-463 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] Akiyama,Shuzo: Dyes and pigments.

    • Related Report
      1987 Annual Research Report
  • [Publications] Akiyama,Shuzo: J.Chem.Soc.,Perkin I.

    • Related Report
      1987 Annual Research Report

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Published: 1987-04-01   Modified: 2016-04-21  

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