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meso-Ester Corroles.

Gabriel Canard1, Di Gao, Anthony D'Aléo

  • 1Aix Marseille Université, CNRS UMR 7325, Centre Interdisciplinaire de Nanosciences de Marseille (CINaM), 13288 Marseille (France), Fax: (+33) 491-41-8916 http://www.cinam.univ-mrs.fr. gabriel.canard@univ-amu.fr.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|March 20, 2015
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Summary

Introducing ester groups to corroles enhances their stability and shifts their spectra. This study explores 16 different diester corroles, revealing how substituents influence their photophysical and electrochemical properties.

Keywords:
corroleselectrochemistryestersluminescenceporphyrinoids

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Area of Science:

  • Organic Chemistry
  • Photochemistry
  • Materials Science

Background:

  • Corroles are macrocyclic compounds with unique electronic and optical properties.
  • Modifying corrole structures can tune their stability and spectral characteristics.
  • Ester groups are known electron-withdrawing substituents that can impact molecular properties.

Purpose of the Study:

  • To investigate the effect of ester groups at the 5- and 15-meso positions of corroles.
  • To understand how these ester substituents influence corrole stability and spectral properties.
  • To explore the impact of different substituents at the third meso position on these effects.

Main Methods:

  • Synthesis and characterization of 16 different 5,15-diester corroles.
  • Photophysical characterization (absorption and emission spectra).
  • Electrochemical characterization.
  • Single-crystal X-ray structure analysis.
  • Density Functional Theory (DFT) and time-dependent DFT calculations.

Main Results:

  • Ester groups at the 5- and 15-meso positions stabilize corroles against oxidation.
  • These substituents cause a redshift in absorption and emission spectra.
  • DFT calculations confirm the electron-withdrawing nature of ester groups and their π-overlap with the corrole system.
  • Crystal packing analysis reveals close chromophore stacking in certain diester corroles due to low steric hindrance.
  • Intermolecular interactions involving inner hydrogen and nitrogen atoms stabilize a specific corrole tautomeric form.

Conclusions:

  • 5,15-diester substitution is an effective strategy for stabilizing corroles and tuning their optical properties.
  • The electronic and structural features of meso-substituents significantly impact corrole behavior.
  • Close π-π stacking in the solid state can be achieved, potentially useful for materials applications.