With peripheral fluorination and chlorination known to significantly influence the solubility, fluorescence quantum yield and redox properties of boron subphthalocyanines (BsubPcs), it is the intent of this study to further expand a matrix of BsubPcs to correlate structural changes to properties. Here, we have adapted previous synthetic methodologies for accessing axially substituted BsubPcs with a variety of alkyne substituents along with incorporating various peripheral halogens. While axial substitution of BsubPcs results in minimal shifts of longest‐wavelength absorptions, relative fluorescence quantum yields decrease with the increasing number of axial carbon–carbon triple bonds. Cyclic voltammetry studies reveal that BsubPcs can form a radical anion more easily with each additional carbon–carbon triple bond, the most significant change happening when going from one to two triple bonds. Also, the reduction profile is influenced by peripheral halogenation as well as by the radical‐stabilizing ability of an axial arylethynyl group. In all, axial alkyne‐based substituents have influential impact on the characteristics of BsubPcs.

中文翻译：

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探索具有碳基官能团的轴向取代的硼亚酞菁硼的合成和电子性质

已知周围的氟化和氯化作用会显着影响硼亚酞菁硼（BsubPcs）的溶解度，荧光量子产率和氧化还原特性，因此本研究的目的是进一步扩展BsubPcs的基质以使结构变化与性能相关。在这里，我们已经调整了以前的合成方法，以获取带有各种炔烃取代基的轴向取代的BsubPcs以及掺入各种外围卤素。虽然BsubPcs的轴向取代导致最长波长吸收的位移最小，但相对荧光量子产率却随轴向碳-碳三键数量的增加而降低。循环伏安法研究表明，每个额外的碳-碳三键，BsubPcs都可以更轻松地形成自由基阴离子，从一键到两个三键时发生的变化最大。同样，还原分布受外围卤化以及轴向芳基乙炔基自由基稳定能力的影响。总之，基于轴向炔烃的取代基对BsubPcs的特性有影响。