Dibenzothiophene-Containing Thiacarbaporphyrinoids.

Area of Science:

• Organic Chemistry
• Supramolecular Chemistry
• Materials Science

Background:

• Expanded porphyrinoids are macrocyclic compounds with unique electronic and optical properties.
• Dibenzothiophene incorporation can modulate the photophysical characteristics of macrocyclic systems.

Purpose of the Study:

• To synthesize and characterize a novel dibenzothiophene-containing thiacarbaporphyrinoid.
• To investigate the structural, spectral, and electrochemical properties of the new macrocycle.

Main Methods:

• Multi-step organic synthesis starting from dibenzothiophene.
• X-ray crystallography for structural elucidation.
• UV-Vis spectroscopy, NMR spectroscopy, and cyclic voltammetry for property analysis.

Main Results:

• Successful synthesis of a six-step dibenzothiophene-containing thiacarbaporphyrinoid.
• X-ray structure revealed a highly nonplanar macrocycle with localized π-conjugation within the thiatripyrrin moiety.
• Spectroscopic studies indicated nonaromaticity, with absorption bands in the visible and near-infrared regions.
• Electrochemical studies demonstrated the electron-rich nature of the macrocycles.

Conclusions:

• The synthesized macrocycle possesses a unique nonplanar structure influencing its electronic properties.
• The dibenzothiophene unit does not extend π-conjugation across the entire macrocycle.
• The macrocycles exhibit interesting optical properties, particularly in their diprotonated forms, suggesting potential applications in optoelectronics.