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Preparation of Novel Organic Functional Materials with different Responding Units for Outer Stimuli

Research Project

Project/Area Number 13440213
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field 機能・物性・材料
Research InstitutionHimeji Institute of Technology

Principal Investigator

NAKATSUJI Shin'ichi  Himeji Institute of Technology, Department of Material Science, Professor, 大学院・理学研究科, 教授 (90124833)

Co-Investigator(Kenkyū-buntansha) AKUTSU Hiroki  Himeji Institute of Technology, Department of Material Science, Research Associate, 大学院・理学研究科, 助手 (80316033)
Project Period (FY) 2001 – 2003
Project Status Completed (Fiscal Year 2003)
Budget Amount *help
¥7,300,000 (Direct Cost: ¥7,300,000)
Fiscal Year 2003: ¥1,900,000 (Direct Cost: ¥1,900,000)
Fiscal Year 2002: ¥1,900,000 (Direct Cost: ¥1,900,000)
Fiscal Year 2001: ¥3,500,000 (Direct Cost: ¥3,500,000)
KeywordsOrganic Functional Material / Functional Spin System / Magnetic Property / Conducting Property / Photo-functionality / Liquid Crystalline Property / Aminoxyl Radical / TEMPO Radical / アミノキシルラジカル / ラジカルアニオン
Research Abstract

In order to develop novel organic functional materials with different responding units to outer stimuli, such as light, heat, electric field, the following efforts were made in the last three years.
The preparation of several organic photo-responsive materials was carried out to tune their physical properties, such as magnetic property, conductivity, or liquid crystalline property, being based on the structural change evoked by the outer stimulus of light. Although so far no organic photo-responsive conductors or liquid crystalline materials could be obtained in spite of our efforts, several organic photo-responsive spin systems could be prepared. A couple of naphthopyran derivatives with aminoxyls were found to show the changes of their intermolecular magnetic interactions with Curie-Weiss model by irradiation and the intermolecular spin-spin interactions of an azobenzene with long alkoxy group and a TEMPO radical at an end were found to be switched by irradiation from weak ferromagnet … More ic interactions with Curi-Weiss behavior to relatively strong antiferromagnetic interactions with singlet-triplet behavior and vice versa.
During the course of our studies to prepare organic heat-responsive materials, a couple of spin systems with heat responsive property could be obtained. The intermolecular magnetic interactions of a heptylbiphenyl derivative with N-methylamido-TEMPO substituent was found to be changed from singlet-triplet behavior to Curie-Weiss one by merely heating over the thermal phase transition temperature, while, on the contrary, the original Curie-Weiss behavior of a cyanobiphenyl derivative with long alkoxy and a TEMPO group was coverted to singlet-triplet one by heating. Several biradical compounds with a naphthalene, biphenyl, azobenzene or azoxybenzene core and long alkoxy as well as TEMPO substituents at both their ends were found to show fairly large interermolecular magnetic interactions based on singlet-triplet model and the interactions were suggested to be originated from the unique supramolecular structural features according to their X-ray analyses.
Several radical catin salts containing TEMPO radicals in anionic part and TTF derivatives in cationic part were prepared and, among them, a BEDT-TTF salt with TEMPO-sulfonate showed semi-conductive property with relatively high conductivity at room temperature together with weak ferromagnetic behavior based on 1-D Heisenberg model and their structure-property relationship could be clarified based on the X-ray crystal structure analysis. Less

Report

(4 results)
  • 2003 Annual Research Report   Final Research Report Summary
  • 2002 Annual Research Report
  • 2001 Annual Research Report
  • Research Products

    (47 results)

All Other

All Publications (47 results)

  • [Publications] 中辻慎一: "複合機能性スピン系を指向した有機ラジカル化合物類の合成と性質"有機合成化学協会誌. 61. 670-681 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] S.Nakatsuji et al.: "Preparation and Magnetic Properties of Radical Anion Salts Derived from Styrylpyriliums and the Corresponding Photo-Dimers"Bulletin of the Chemical Society of Japan. 76. 1245-1250 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Akutsu et al.: "New BEDT-TTF-based Organic Conductor Including an Organic Anion Derived from TEMPO Radical, α-(BEDT-TTF)_3(TEMPO-NHCOCH_2SO_3)_2・6H_2)"Chemistry Letters. 32. 1118-1119 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Kaneko et al.: "Photochromic Radical Compounds Based on a Naphthopyran System"Organic Letters. 5. 2127-2129 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Akutsu et al.: "Tetrathiafulvalenium 4-oxo-2,2,6,6-tetramethylpiperidinyloxy-4-sulfate"Acta Crystallographica. Acta. o1441-o1443 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Akutsu et al.: "Superstructures of donor packing arrangements in a series of molecular charge transfer salts"Chemical Communications. 18-19 (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] S.Nakatsuji: "Organic Multifunctional Spin Systems Based on Aminoxyl Radicals"Adv.Mater.. 13. 1719-1724 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Ikemoto, H.Akutsu, J.Yamada, S.Nakatsuji: "Aminoxyl Radicals Bearing a Mesogenic Core"Tetrahedron Lett.. 42. 6873-6875 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Akutsu, J.Yamada, S.Nakatsuji: "A New Organic Anion Consisting of the TEMPO Radical for Charge-Transfer Salts: 2,2,6,6-Tetramethylpiperidinyloxy-4-Sulfamate (TEMPO-NHSO_<3^-> )"Chem.Lett.. 208-209 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] S.Nakatsuji, S.Takeuchi, T.Ojima, Y.Ogawa, H.Akutsu, J.Yamada: "Preparation and Properties of Photo-Functional Systems with Nitroxide Radicals"Mol.Cryst.Liq.Cryst.. 356. 23-32 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] S.Nakatsuji, M.Mizumoto, K.Kitamura, H.Akutsu, J.Yamada: "Preparation and Properties of Biphenyl and Cholesterol Derivatives with Nitroxide Radicals"Mol.Cryst.Liq.Cryst.. 356. 33-40 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Ojima, H.Akutsu, J.Yamada, S.Nakatsuji: "Magnetic Properties of Anthracene Derivatives and the Corresponding Photo-Dimers with Stable Radical Substituents"Polyhedron. 20. 1335-1338 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Mizumoto, H.Ikemoto, H.Akutsu, J.Yamada, S.Nakatsuji: "Preparation and Properties of Novel Mesogenic Spin System"Mol.Cryst.Liq.Cryst.. 363. 149-156 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Akutsu, J.Yamada, S.Nakatsuji: "Preparation and Characterization of Novel Organic Radical Anions for Organic Conductors : TEMPO-NHSO_<3^-> and TEMPO-OSO_<3^->"Synth.Met.. 120. 871-872 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Mito, T.Tanimoto, T.Kawase, M.Hitaka, S.Nakatsuji, H.Morimoto, H.Anzai: "Measurements of Magnetic Susceptibility of a Genuine Organic Bulk-Ferromagnet at High Pressures in DAC"Polyhedron. 20. 1505-1508 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] S.Nakatsuji, T.Ojima, H.Akutsu, J.Yamada: "Anthracene Derivatives and the Corresponding Dimers with TEMPO Radicals"J.Org.Chem.. 67. 916-921 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] S.Nakatsuji, M.Mizumoto, H.Ikemoto, H.Akutsu, J.Yamada: "Preparation and Properties of Organic Radical Compounds with Mesogenic Cores"Eur.J.Org.Chem.. 1912-1918 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] S.Nakatsuji, H.Ikemoto, H.Akutsu, J.Yamada, A.Mori: "Novel radical Compounds Bearing Mesogenic Cores with Long Alkyl Substituents"J.Org.Chem.. 68. 1708-1714 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] S.Nakatsuji, Y.Ogawa, J.Yamada: "Preparation and Magnetic Properties of Radical Anion Salts Derived from Styrylpyryliums and the Corresponding Photo-Dimers"Bull.Chem.Soc.Jpn.. 76. 1245-1250 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Kaneko, H.Akutsu, J.Yamada, S.Nakatsuji: "Photochromic Radical Compounds Based on a Naphthopyran System"Org.Lett.. 5. 2127-2129 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] 中辻慎一: "複合機能スピン系を指向した有機ラジカル化合物類の合成と性質"有機合成化学協会誌. 61. 670-681 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Akutsu, J.Yamada, S.Nakatsuji: "New BEDT-TTF-based Organic Conductor Including an Organic Anion Derived from the TEMPO Radical, α-(BEDT-TTF)_3(TEMPO-NHCOC_2SO_3)_2・6H_2O"Chem.Lett.. 32. 1118-1119 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Akutsu, J.Yamada, S.Nakatsuji: "Tetraphenylphosphonium 4-hydroxy-2,2,6,6-tetramethylpiperidin-piperidinloxy-4-sulfonate"Acta Cryst. C59. o433-o434 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Akutsu, J.Yamada, S.Nakatsuji: "Tetrathiafulvalenium 4-oxo-2,2,6,6-tetramethylpiperidin-1-sulfate"Acta Cryst. E59. o1441-o1443 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Mito, H.Deguchi, T.Tanimoto, T.Kawase, S.Nakatsuji, H.Morimoto, H.Anzai, H.Nakano, Y.Murakami, K.Takeda: "Pressure effects on an organic radical ferromagnet : 2,5-difluorophenyl-α-nitronyl nitroxide"Phys.Rev.. B67. 024427-1-024427-8 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Ogawa, T.Ojima, H.Akutsu, J.Yamada, S.Nakatsuji: "Structures and Properties of Organic Photo-responsive Spin Systems"Mol.Cryst.Liq.Cryst.. 390. 97-104 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Akutsu, A.Akutsu-Sato, S.S.Turner, P.Day, E.Canadell, S.Firth, R.J.H.Clark, J.Yamada, S.Nakatsuji: "Superstructures of donor packing arrangements in a series of molecular charge transfer salts"Chem.Commun.. 18-19 (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.amano, H.Akutsu, J.Yamada, S.Nakatsuji: "Structures and Magnetic Properties of Organic Radical Compounds with an Aromatic Core and Long alkyl Groups"Chem.Lett.. 33. 382-383 (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] 中辻慎一: "複合機能性スピン系を指向した有機ラジアル化合物類の合成と性質"有機合成化学協会誌. 61. 670-681 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] S.Nakatsuji et al.: "Preparation and Magnetic Properties of Radical Anion Salts Derived from Styrylpyriliums and the Corresponding Photo-Dimers"Bulletin of the Chemical Society of Japan. 76. 1245-1250 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] H.Akutsu et al.: "New BEDT-TTF-based Organic Conductor Including an Organic Anion Derived from TEMPO Radical,α-(BEDT-TTF)_3(TEMPO-NHCOCH_2SO_3)_2・6H_2O"Chemistry Letters. 32. 1118-1119 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] T.Kaneko et al.: "Photochromic Radical Compounds Based on a Naphthopyran System"Organic Letters. 5. 2127-2129 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] H.Akutsu et al.: "Tetrathiafulvalenium 4-oxo-2,2,6,6-tetramethylpiperidinyloxy-4-sulfate"Acta Crystallography. E59. o1441-o1443 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] H.Akutsu et al.: "Superstructures of donor packing arrangements in a series of molecular charge transfer salts"Chemical Communications. 18-19 (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] S.Nakatsuji et al.: "Preparation and Properties of Organic Radical Compounds with Mesogenic Cores"European Journal of Organic Chemistry. 1912-1918 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] S.Nakatsuji: "Recent progress in the development of organic spin systems with multi-property"Recent Research Developments in Organic & Bioorganic Chemistry. 6. 1-26 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] J.Yamada et al.: "2-(1,3-Dithiolan-2-ylidene)-5-(1,3-dithian-2-ylidene)-1,3,4,6-tetrathiapentalene (DHDA-TTP), a hybrid of BDH-TTP and BDA, and its metallic cation-radical salts"Chemical Communications. 1118-1119 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] J.Yamada et al.: "New Organic Superconductors from a Non-TTF Donor, BDA-TTP"Molecular Crystals & Liquid Crystal. 380. 145-150 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] H.Yoshino et al.: "Electrical Properties of Organic Conductors at High Temperature"Molecular Crystals & Liquid Crystal. 380. 239-244 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] S.Nakatsuji et al.: "Novel Radical Compounds Bearing Mesogenic Cores with Long Alkyl Substituer"Journal of Organic Chemistry. 68. 1708-1714 (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] T.Ojima et al.: "Magnetic Properties of Anthracene Derivatives and the Corresponding Photo-Dimers with Stable Radical Substituents"Polyhedron. 20. 1505-1508 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] H.Akutsu et al.: "A New Organic Anion Consisting of the TEMPO Radical for Organic Charge-Transfer Salts"Chemistry Letters. 208-209 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] M.Mizumoto et al.: "Preparation and Properties of Novel Mesogenic Spin Systems"Molecular Crystal & Liquid Crystals. 363. 149-156 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] H.Ikemoto et al.: "Aminoxyl Radicals Bearing a Mesogenic Core"Tetrahedron Letters. 42. 6873-6875 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] S.Nakatsuji: "Organic Multifunctional Spin Systems Based on Aminoxyl Radicals"Advanced Materials. 13. 1719-1724 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] S.Nakatsuji et al.: "Anthracene Derivatives and the Corresponding Dimers with TEMPO Radicals"Journal of Organic Chemistry. 67. 916-921 (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] 安西弘行, 中辻慎一: "有機電子物性"培風館. 141 (2001)

    • Related Report
      2001 Annual Research Report

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Published: 2001-04-01   Modified: 2016-04-21  

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