Mizrahi Amir, Bukuroshi Esmeralda, Vestfrid Jenya, Bender Timothy P, Gross Zeev
Schulich Faculty of Chemistry, Technion-Israel Institute of Technology, Haifa 3200008, Israel.
Chemistry Department, Nuclear Research Centre Negev, Beer-Sheva 84190, Israel.
Inorg Chem. 2020 Mar 2;59(5):2641-2645. doi: 10.1021/acs.inorgchem.9b03529. Epub 2020 Feb 20.
Chloroboron subphthalocyanines (Cl-BsubPc) are robust compounds that can be readily modified at the axial and peripheral positions. Peripherally chlorinated derivatives were recently found to be advantageous regarding integration into organic electronic devices. We now report on the effects of fluorides introduced on both the peripheral and axial positions of BsubPcs. Specific attention on the reduction of these compounds revealed that the much fewer electronegative chlorides still shift the redox potentials as much as fluorides. The main advantage of the fluorinated derivatives was deduced to be their stability, allowing for the spectroscopic characterization of mono-anionic and even bis-anionic subphthalocyanines. This study sets the precedence for further tuning of the electrochemical properties of BsubPcs through molecular design, thus increasing their applicability regarding organic electronic devices that undergo multiple redox cycles during operational lifetime.
氯硼亚酞菁（Cl-BsubPc）是一类稳定的化合物，其轴向和周边位置易于修饰。最近发现，周边氯化衍生物在集成到有机电子器件方面具有优势。我们现在报告在BsubPc的周边和轴向位置引入氟化物的影响。对这些化合物还原的特别关注表明，电负性小得多的氯化物仍然能像氟化物一样大幅改变氧化还原电位。推断氟化衍生物的主要优势在于其稳定性，这使得单阴离子甚至双阴离子亚酞菁的光谱表征成为可能。这项研究为通过分子设计进一步调节BsubPc的电化学性质奠定了基础，从而提高了它们在工作寿命期间经历多个氧化还原循环的有机电子器件中的适用性。
