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Substituent Effect on Porphyrin Ring Distortion

Research Project

Project/Area Number 10672026
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Physical pharmacy
Research InstitutionTeikyo University

Principal Investigator

TAKEDA Jun  Teikyou University, Faculty of Pharmaceutical Science, Lecturer, 薬学部, 講師 (40197306)

Project Period (FY) 1998 – 1999
Project Status Completed (Fiscal Year 1999)
Budget Amount *help
¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1999: ¥500,000 (Direct Cost: ¥500,000)
KeywordsPorphyrin / Nonplanar Porphyrin / Distortion / Substituent Effect / 非平面構造
Research Abstract

A series of porphyrin with meso-(2,6-difluoro- or dichlorophenyl) substituents has been synthesized by mixed condensation of pyrrole, diphenylpyrrole, and 2,6-difluoro- or 2,6-dichlorobenzaldehyde. The porphyrins reported here are abbreviated as follows: tetraaryl-lporphrins (TXPP), hexaarylporphyrins (HXPP), trans-octarylporphyrins (trans-OXPP), cis-octarylporphyrins (cis-OXPP), decaarylporphyrins (DecXPP), and dodecaarylporphyrins (DXPP), where X=F or Cl.
Increase of the phenyl substituents have large effect on the UV-visible spectra, gradually red-shifting the Soret bands in the order of TXPP<HXPP<trans-OXPP,cis-OXPP<DecXPP<DXPP. However, the magnitude of the red shift is different between X=F series and X=Cl series. It is tempting to suppose that the magnitude of porphyrin ring distortion is different between X=F seris and X=Cl seris. It is possible that interaction between lone pair of fluorin atoms and porphyrin π orbitals reduce the porphyrin ring distortion.
From the acid-base properties of these porphyrins, it is supposed that conjugation between porphyrin ring and meso-phenyl ring has influence upon the porphyrin ring distortion. Furthermore, an unusual stability in the acid monocation state of TXPP (X=F and X=Cl) is observed from the acid-base titration experiments.

Report

(3 results)
  • 1999 Annual Research Report   Final Research Report Summary
  • 1998 Annual Research Report

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

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