Peripheral vs. axial halide substituted boron subphthalocyanines: Structure-property relationship - ICS84 The 84th Annual Meeting of the Israel Chemical Society

Amir Mizrahi ¹ Esmeralda Bukuroshi ³ Zeev Gross ² Alan Lough ⁴ Timothy P. Bender ³

¹Department of Chemistry, Nuclear Research Center Negev, Beer-Sheva, Israel
²Schulich Faculty of Chemistry, Technion – Israel Institute of Technology, Haifa, Israel
³Department of Chemical Engineering and Applied Chemistry, University of Toronto, Toronto, Ontario, Canada
⁴Department of Chemistry, University of Toronto, Toronto, Ontario, Canada

Boron subphthalocyanines (BsubPcs) are semiconducting organic small molecules that are a variant from the widely studied family of phthalocyanine (Pc) macrocycles. BsubPcs are uniquely templated and formed by cyclotrimerization of phthalonitrile in the presence of boron trihalides (BCl₃ and BBr₃). Because of their unique photophysical properties, BsubPcs are applicable within organic electronic devices, such as organic photovoltaics (OPVs) and organic light emitting diodes (OLEDs).

We have now investigated the effect of peripheral and axial fluorination versus chlorination. The structure of these compounds was analyzed and confirmed by ¹H (if applicable), ¹³C and ¹⁹F NMR spectroscopy, elemental analysis, mass spectrometry and x-ray crystallography. The high purity obtained for F-F₆BsubPc and F-F₁₂BsubPc enabled direct points of comparisons against chlorinated analogs to understand the role of relative halogenation in the periphery and axial positions of BsubPcs on their physical properties; assessed and established by cyclic voltammetry, UV/Vis and photoluminescence spectrometry. This study therefore provides a comprehensive and systematic survey of the chemistry and physical properties of fluorinated BsubPcs.