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Development of Non-linear Optical Material involving the Boron Atom

Research Project

Project/Area Number 06554027
Research Category

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

Allocation TypeSingle-year Grants
Research Field Organic chemistry
Research InstitutionYamaguchi University (1995)
Osaka University (1994)

Principal Investigator

SUGIHARA Yoshikazu  Yamaguchi Universtiy, Faculty of Science, Professor, 理学部, 教授 (30112006)

Co-Investigator(Kenkyū-buntansha) NIIMOTO Yoshihide  Sumika Fine Chemicals Ltd., Group manager (Researcher), グループマネージャー
MASAKI Yasuhiro  University of Tokyo, College of Art and Science, Research Associate, 教養学部, 助手 (60199677)
YAMAMOTO Koji  University of Osaka Prefecture, Faculty of Integrated Arts and Sciences, Profess, 総合科学部, 教授 (80029438)
YANO Shigenobu  Nara Women's University, Faculty of Science, Professor, 理学部, 教授 (60011186)
Project Period (FY) 1994 – 1995
Project Status Completed (Fiscal Year 1995)
Budget Amount *help
¥5,500,000 (Direct Cost: ¥5,500,000)
Fiscal Year 1995: ¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1994: ¥3,500,000 (Direct Cost: ¥3,500,000)
Keywordsnon-linear optical materials / polarizability / dipole moment / donor and acceptor of pi-electron / conjugated system involving the boron atom / polarized and stable hetero-aromatic molecule / 青色光透過性
Research Abstract

To date, conjugated systems, each being composed of a donor, an aromatic ring and an acceptor, have been the well-known non-linear optical materials, in particular, for the purpose of second harmonic generation. We consider that the main role of the aromatic ring are to decrease donation of pi-electron from the donor to the acceptor in the electronically ground state and, accordingly, to relatively enhance the interaction in the electronically excited state. In spite of the marked efficiency of these systems, the recent examinations have stressed that the closed-shell character of the aromatic rings endows the systems with the upper-limit as non-linear optical materials.
A trivalent boron is isoelectronic to a carbocation. Hence, it behaves as a pi-electron acceptor. Due to the electropositivity, however, its pi-type conjugation with the carbon atom is considered to be weak like the closed-shell aromatic rings. From this viewpoint we examined borepin annelated with heteroles, such as th … More e pyrrole or thiophene rings both of which are electron donors. After some trials, synthesis of 1-phenylthieno- [3,4-d] borepin (1), 1-phenylthieno [2,3-d] borepin (2), 5-Methyl-1-phenylpyrrolo [3,4-d] borepin (3), and 5-tris (isopropylsilyl)-1-phenylpyrrolo [3,4-d] borepin (4) were achieved. The methods developed are generally useful for the synthesis of conjugated aromatics involving a boron atom. The marked difference in reactivity toward acetic acid was observed with the change of the annelation modes of borepin and heterole rings. The shifts of fluorescent emissions showed the clear linear relationship with the change of solvent-polarity and indicated that the dipole moment of each compound in the excited state is much larger than that in the ground state. The moderate blue-light transparency was observed, despite the above-mentioned charge-transfer character in the excited state.
These findings indicate that conjugated systems involving the boron atom are useful as non-linear optical materials. Less

Report

(3 results)
  • 1995 Annual Research Report   Final Research Report Summary
  • 1994 Annual Research Report
  • Research Products

    (28 results)

All Other

All Publications (28 results)

  • [Publications] 阿部憲孝: "Reactions of 2-Alkylamino-and 2-Dialkylamino-1-azaazulenes with Diphenylcyclopropenones" Heterocycles. 41. 2289-2298 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] 杉原美一: "Cyclopenta [a] phenalen-9 (8H) -one : An Extended Phenalenone System" J.Chem.Soc.,Perkin Trans.1. 2813-2815 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] 杉原美一: "5-Methyl-1-phenylpyrrolo [3,4-d] borepin : A Polarized Aromatic Molecule" J.Chem.Soc.,Chem.Commun.1249-1250 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] 中沢知男: "The Reactions of 4,5-Dehydrotropone with 4-Phenyloxazols" Tetrahedron Lett.35. 8421-8424 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] 杉原美一: "The Structure of Diethyl (3-pyridyl) borane" J.Chem.Soc.,Chem.Commun.1925-1926 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] 杉原美一: "Thienoborepins : Conjugation Characteristics of Boron Heterocycles" Tetrahedron. 50. 6495-6504 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] N.Abe: "Reactions of 2-Alkylamino- and 2-Dialkylamino-1-azaazulenes with Diphenylcyclopropenones" Heterocycles. 41, No.10. 2289-2298 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Y.Sugihara: "Cyclopenta [a] phenalen-9 (8H) - one : An Extended Phenalenone System, 1995" J.Chem.Soc., Perkin Trans.1. No.22. 2813-2815 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Y.Sugihara: "5-Methyl-1-phenylpyrrolo [3,4-d] borepin : A Polarized Aromatic Molecule" J.Chem.Soc., Chem.Commum.No.12. 1249-1250 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] S.Wakabayashi: "Some Preparation Methods of a Tricyclo [4.1.0.0^<2,7>] -hept-4-en-3-one Skeleton" Synth.Commun.25, No.13. 2019-2027 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] T.Tanase: "Synthesis and Characterization of (m-Alkoxo) bis- (m-carboxylato) diruthenium Complexes, Na [Ru_2 (dhpta) (m-O_2CR_2] (dhptaH_5=1,3-diamino-2-hydroxypropane tetraacetic acid). A Ruthenium Analogue of Model Systems for Iron-oxo Proteins" Chem.Lett.No.10. 1853-1856 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] T.Nakazawa: "The Reactions of 4,5-Dehydrotropone with 4-Phenyloxazols" Tetrahedron Lett.35. 8421-8424 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Y.Sugihara: "The Structure of Diethyl (3-pyridyl) borane" J.Chem.Soc., Chem.Commun.1925-1926 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] S.Yano: "Chemical Modification of Metal Complexes. An Efficient Procedure for O-Acylation of an Anionic Metal Complex Having a Non-coordinated Hydroxy Group" Inorg.Chem.33. 5030-5035 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Y.Sugihara: "Thienoborepins : Conjugation Characteristics of Boron Heterocycles" Tetrahedron. 50, No.22. 6495-6504 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] N.Abe: "Reactions of 2-Alkylamino-and 2-Dialkylamino-1-azaazulenes with Diphenylcyclopropenones" Heterocycles. 41. 2289-2298 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Y.Sugihara: "Cyclopenta [a] phenalen-9 (8H) -one : An Extended Phenalenone System" J.Chem.Soc.Perkin Trans.1. 2813-2815 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Y.Sugihara: "5-Methyl-1-phenylpyrrolo [3,4-d] borepin : A Polarized Aromatic Molecule" J.Chem.Soc.,Chem.Commun.1249-1250 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] T.Nakazawa: "The Reactions of 4,5-Dehydrotropone with 4-Phenyloxazola" Texrahedron Lett.35. 8421-8424 (1994)

    • Related Report
      1995 Annual Research Report
  • [Publications] Y.Sugihara: "The Structure of Diethyl (3-pyridyl) borane" J.Chem.Soc.,Chem.Commun.1925-1926 (1994)

    • Related Report
      1995 Annual Research Report
  • [Publications] Y.Sugihara: "Thienoborepins : Conjugation Characteristics of Boron Heterocycles" Tetrahedron. 50. 6495-6504 (1994)

    • Related Report
      1995 Annual Research Report
  • [Publications] Y.Sugihara: "Thienoborepins:Conjugation Characterisrics of Boron Heterocycles" Tetrahedron. 50. 6495-6504 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] S.Yano: "Chemical Modification of Metal Complexes.An Efficient Procedure for O-Acylation of an Anionic Metal Complex Having a Non-coordinated Hydroxy Group" Inorg.Chem.33. 5030-5035 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Y.Sugihara: "The Structure of Diethyl(3-pyridy1)borane" J.Chem.Soc.,Chem.Commun.1925-1926 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] T.Tanase: "Synthesis and Characterization of (m-Alkoxo)bis(m-carboxylato)diruthenium Complexes,Na[Ru_2(dhpta)(m-O_2CR_2].A Ruthenium Analogue of Model Systems for Iron-oxo Proteins" Chem.Lett.1853-1856 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] T.Nakazawa: "The Reaction of 4,5-Dehydrotropone with 4-Phenyloxazols" Tetrahedron Lett.35. 8421-8424 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] S.Wakabayashi: "Some Preparation Methods of a Tricyclo[4.1.0.0^<2,7>]hept-4-en-3-one Skeleton" Synth.Commun.(in press). (1995)

    • Related Report
      1994 Annual Research Report
  • [Publications] Y.Sugihara: "5-Methyl-1-phenylpyrrolo[3,4-d]borepin:A Polarized Aromatic Molecule" J.Chem.Soc.,Chem.Commun.(in press). (1995)

    • Related Report
      1994 Annual Research Report

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Published: 1994-04-01   Modified: 2016-04-21  

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