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2019 Fiscal Year Research-status Report

3D spatial imaging of chirality using nuclear magnetic resonance (NMR)

Research Project

Project/Area Number 19K05229
Research InstitutionNational Institute for Materials Science

Principal Investigator

Labuta Jan  国立研究開発法人物質・材料研究機構, 国際ナノアーキテクトニクス研究拠点, 主任研究員 (00720690)

Project Period (FY) 2019-04-01 – 2022-03-31
KeywordsChirality / Porphyrin / Physical chemistry / NMR imaging
Outline of Annual Research Achievements

Chirality is a key feature in many biological events. The two enantiomers of the same molecule differ when interacting with other chiral species. This is especially important in development of new pharmaceuticals where their pharmacological effect depends on identity of enantiomer. We aim to develop NMR method and porphyrin-based molecular detector for 3D spatial and temporal monitoring of chirality in ongoing chemical reactions or in living systems.
In FY2019 we have synthesized several porphyrin-based systems for chirality sensing, anion sensing and organo-catalytic applications. We have shown that the designed structures have promising applications in all three areas. Preliminary results show that several porphyrin-based candidates seem to be very effective as a chirality sensors (i.e. enantiomeric excess sensors) using nuclear magnetic resonance (NMR) spectroscopy as a probing method. We have also developed robust method based on peripherally functionalized porphyrin-derivative for enhanced anion binding and/or detection.

Current Status of Research Progress
Current Status of Research Progress

2: Research has progressed on the whole more than it was originally planned.

Reason

The research plan is in progress as scheduled.

Strategy for Future Research Activity

In FY2020 we plan to exploit and improve the sensing and catalytic potential of synthesized molecules. Moreover, more of the water soluble analogues will be made based on rational synthesis in order to ensure the sensing capabilities in water. The 3D spatial NMR chirality (enantiomeric excess) detection experiments will be carried out.

Causes of Carryover

I wanted to attend workshop(lessons) on processing of spectroscopic data, however, the event was cancelled. Therefore I would like to roll the money over to next FY.

  • Research Products

    (10 results)

All 2020 2019

All Journal Article (5 results) (of which Int'l Joint Research: 5 results,  Peer Reviewed: 5 results) Presentation (5 results) (of which Int'l Joint Research: 5 results,  Invited: 4 results)

  • [Journal Article] meso-Tetraphenylporphine as a prochiral solvating agent (pro-CSA): A physicochemical study2020

    • Author(s)
      Jan Labuta, Shinsuke Ishihara, Jonathan P. Hill
    • Journal Title

      J. Porphyrins Phthalocyanines

      Volume: 24 Pages: 320-329

    • DOI

      10.1142/S1088424619501141

    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Diporphyrin tweezer for multichannel spectroscopic analysis of enantiomeric excess2020

    • Author(s)
      Daniel T. Payne, Mandeep K. Chahal, Vaclav Brezina, Whitney A. Webre, Katsuhiko Ariga, Francis D’Souza, Jan Labuta, Jonathan P. Hill
    • Journal Title

      Front. Chem. Sci. Eng.

      Volume: 14 Pages: 28-40

    • DOI

      10.1007/s11705-019-1869-1

    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Molecular Engineering of β-Substituted Oxoporphyrinogens for Hydrogen-Bond Donor Catalysis2020

    • Author(s)
      Mandeep K. Chahal, Daniel T. Payne, Yoshitaka Matsushita, Jan Labuta, Katsuhiko Ariga, Jonathan P. Hill
    • Journal Title

      Eur. J. Org. Chem.

      Volume: - Pages: 82-90

    • DOI

      10.1002/ejoc.201901706

    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Knock-on synthesis of tritopic calix[4]pyrrole host for enhanced anion interactions2019

    • Author(s)
      Mandeep K. Chahal, Jan Labuta, Vaclav Brezina, Paul A. Karr, Yoshitaka Matsushita, Whitney A. Webre, Daniel T. Payne, Katsuhiko Ariga, Francis D’Souza, Jonathan P. Hill
    • Journal Title

      Dalton Trans.

      Volume: 48 Pages: 15583-15596

    • DOI

      10.1039/C9DT02365H

    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Increasing the complexity of oxoporphyrinogen colorimetric sensing chromophores: N-alkylation and β-substitution2019

    • Author(s)
      Mandeep K. Chahal, Nadiia Velychkivska, Whitney A. Webre, Jan Labuta, Shinsuke Ishihara, Katsuhiko Ariga, Francis D’Souza, Jonathan P. Hill
    • Journal Title

      J. Porphyrins Phthalocyanines

      Volume: 23 Pages: 1184-1194

    • DOI

      10.1142/S1088424619501463

    • Peer Reviewed / Int'l Joint Research
  • [Presentation] Porphyrins as Multi-responsive Sensors2019

    • Author(s)
      Jan Labuta
    • Organizer
      MANA International Symposium 2019
    • Int'l Joint Research
  • [Presentation] Diverse Properties of Porphyrin Derivatives2019

    • Author(s)
      Jan Labuta
    • Organizer
      The 3rd International Workshop on MEMS and Sensor System 2019 (IWMS 2019)
    • Int'l Joint Research / Invited
  • [Presentation] Multi-responsive Porphyrins for Sensing Applications2019

    • Author(s)
      Jan Labuta
    • Organizer
      The 2019 Spring Meeting of the European Materials Research Society (E-MRS)
    • Int'l Joint Research / Invited
  • [Presentation] Porphyrins as Multi-responsive Sensors2019

    • Author(s)
      Jan Labuta
    • Organizer
      The 8th Asian Conference on Colloid & Interface Science (ACCIS-2019)
    • Int'l Joint Research / Invited
  • [Presentation] From Polymers to Porphyrins and Back Again - My Research Journey in Japan2019

    • Author(s)
      Jan Labuta
    • Organizer
      9th CSJ Chemistry Festa (Chemical Society of Japan)
    • Int'l Joint Research / Invited

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Published: 2021-01-27  

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