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Synthesis and solid state Chemistry of push-pull type substituted allene derivatives

Research Project

Project/Area Number 11640543
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionKitasato University

Principal Investigator

MAZAKI Yasuhiro  Kitasato University, School of Science, Associate Professor, 理学部, 助教授 (60199677)

Project Period (FY) 1999 – 2000
Project Status Completed (Fiscal Year 2001)
Budget Amount *help
¥3,300,000 (Direct Cost: ¥3,300,000)
Fiscal Year 2000: ¥1,800,000 (Direct Cost: ¥1,800,000)
Fiscal Year 1999: ¥1,500,000 (Direct Cost: ¥1,500,000)
Keywordsallene derivatives / synthesis / push-pull type substitution / solid state chemistry / 固体化学 / アレン誘導体 / 分極 / カルベノイド / 結晶 / 有機合成
Research Abstract

1-(4N,N-Dimethylaminophenyl)-3-(4-nitrophenyl)-1,3-diphenylallene 1 (pale yellow liquid) and 1-(4-carbomethoxyphenyl)-3-(4-N,N-dimethylarrunophenyl)-1,3- diphenylallene 2 (colorless solid) have been synthesized as push-pull type substituted allene derivatives and examined their properties caused by push-pull type polarization. 1-(4-N,N-dimethylaminophenyl)-1,3,3-triphenyl-allene 3, 1-(4-nitrophenyl)-1,3,3-triphenylallene 4, 1-(4- carbomethoxyphenyl) -1,3,3- triphenylallene 5, tetraphenylallene 6 have been also synthesized as the reference compounds.
Although it is expected the reciprocally opposite polarization effects of both substituents (push and pull) raise the contribution of "carbene like" resonance structure in allene moiety, it has been suggested that the polarization through benzene rings was little effective to allene part by the comparison of X-ray molecular structures of reference compounds 3 and 6, 13C NMR chemical shifts and electronic spectra in these series.
X-ray crystallographic analysis of push-pull derivatives, examination of enclathration for 1 and 2, solid state photoreaction of 1, 2 were prevented by low stability and poor crystallinity of 1 and 2.

Report

(3 results)
  • 2001 Final Research Report Summary
  • 2000 Annual Research Report
  • 1999 Annual Research Report
  • Research Products

    (2 results)

All Other

All Publications (2 results)

  • [Publications] Irie, S: "STM Study on Photopolymerization of 17, 19-hexatriacontadiyne Monolayer"Probe Microscopy. 2. 1-9 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Irie. S, Isoda. S, Kobayashi. T, Ozaki. H, Mzaki. Y: "STM Study on Photopolymerization of 17, 1 9-hexatriacoritadiyne Monolayer"Probe Microscopy. Vol.2. 1-9 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary

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Published: 1999-04-01   Modified: 2016-04-21  

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