Development of three-dimensional pi-electronic compounds originated from tripyrrin subunits

2014 Fiscal Year Final Research Report

• Project/Area Number: 24750034
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Organic chemistry
• Research Institution: Shimane University (2014); Chiba University (2012-2013)
• Principal Investigator: SUZUKI Masaaki 島根大学, 総合理工学研究科(研究院), 講師 (90506891)
• Project Period (FY): 2012-04-01 – 2015-03-31
• Keywords: ポルフィリノイド / 環拡張ポルフィリン / ペンタフィリン / 芳香族性 / トリフルオロメチル化

Outline of Final Research Achievements

The major target of this project utilizing tripyrrine precursors was switched to development of a wide variety of three-dimensional π-systems. As a result, it was successfully achieved that novel three-dimensionalπ-electronic modes bearing a branchedπ-plane had been constructed based on peculiar nucleophilic substitution reactions onto recombined N-fused pentaphyrin bromide. In the meantime, meso-trifluoromethyl substituted octaalkylporphyrins were obtained by scrambling side reactions of oligo-pyrrolic precursors. The strongly electron-withdrawing nature and the spatial steric hindrance of trifluoromethyl group caused a large distortion of the macrocyclic plane and improvement of the absorption property. Furthermore, the trifluoromethyl groups undertook solvolysis when the centeral metal ion was zinc, affording meso-methoxycarbonyl derivatives.

Free Research Field

有機化学