Exploration of Excited State Properties of Heteroporphyrins

2021 Fiscal Year Final Research Report

• Project/Area Number: 17H01190
• Research Category: Grant-in-Aid for Scientific Research (A)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Nagoya University
• Principal Investigator: Shinokubo Hiroshi 名古屋大学, 工学研究科, 教授 (50281100)
• Project Period (FY): 2017-04-01 – 2022-03-31
• Keywords: ポルフィリン / ヘテロ原子 / 芳香族性 / 反芳香族性 / 光物性 / 励起状態 / π電子化合物 / 光線力学療法

Outline of Final Research Achievements

A variety of heteroatoms were introduced in the porphyrin skeleton to obtain novel heteroatom-embedded porphyrins via metal-templated synthesis. The heteroporphyrins exhibited aromaticity or antiaromaticity depending on the nature of introduced heteroatoms. The optical properties such as absorption and emission wavelengths and the excited state dynamics were also controlled by the proper choice of heteroatoms. In particular, diazaporphyrin derivatives effectively absorb near-infrared light and serve as potent photosensitizers for photodynamic therapy. An oxaporphyrin cobalt complex combined with a heme acquisition protein HasA strongly inhibited the growth of P. aeruginosa and multidrug-resistant P. aeruginosa.

Free Research Field

有機化学

Academic Significance and Societal Importance of the Research Achievements

機能性色素として多方面に応用されるポルフィリンに対してヘテロ原子を導入する方法を確立したことで、ポルフィリンの物性変調の手法を格段に拡大することができた。高性能な近赤外色素の開発につながる成果と言える。実際、窒素を導入したジアザポルフィリンが光線力学療法によるがん治療のための光増感剤として可能性をもつことを生物学的実験により示すことができた。