Synthesis and properties of fused-ring-expanded porphyrins that were core-modified with Group 16 heteroatoms

Hai Jun Xu, John MacK, Di Wu, Zhao Li Xue, Ana B. Descalzo, Knut Rurack, Nagao Kobayashi, Zhen Shen

Research output: Contribution to journalArticlepeer-review

32 Citations (Scopus)

Abstract

The synthesis of a series of novel core-modified and fused-ring-expanded tetraphenylporphyrins is reported. Theoretical calculations and magnetic circular dichroism (MCD) and fluorescence spectroscopic measurements were used to analyze the effect of core modification with Group 16 oxygen, sulfur, selenium, and tellurium atoms on the optical properties and electronic structures of the porphyrins. Marked redshifts of the Q and B bands and accelerated intersystem-crossing rates were observed, thus making these compounds potentially suitable for use in a variety of applications. The scope for further fine-tuning of these optical properties based on additional structural modifications, such as the incorporation of fused benzene rings to form ABAB structures by using a thiophene precursor with a fused bicyclo[2.2.2]octadiene ring and the introduction of various substituents onto the meso-phenyl rings, is also examined. Core-modified porphyrinoids: The synthesis of a series of novel core-modified and fused-ring-expanded tetraphenylporphyrins is reported (see figure). Theoretical calculations, magnetic circular dichroism (MCD), and fluorescence emission spectroscopy are used to analyze the effect of core modification with Group 16 oxygen, sulfur, selenium, and tellurium atoms on the optical properties and electronic structures.

Original languageEnglish
Pages (from-to)16844-16867
Number of pages24
JournalChemistry - A European Journal
Volume18
Issue number52
DOIs
Publication statusPublished - 2012

Keywords

  • MCD spectroscopy
  • density functional calculations
  • fluorescence
  • porphyrinoids
  • ring expansion

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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