Abstract
AbstractA new boron subphthalocyanine (SubPc) derivative with a terminal alkyne substituent on the central boron atom was prepared by substitution of a triflate at the boron atom with but‐3‐yn‐1‐ol. This compound was shown to be a versatile building block for metal‐catalyzed coupling reactions, such as modified Glaser–Hay, Cadiot–Chodkiewicz, and Sonogashira reactions as well as the copper(I)‐catalyzed azide‐alkyne cycloaddition (CuAAC). For example, metal‐catalyzed reactions provided access to a SubPc dimer containing a butadiyne bridging unit, two different SubPc‐fullerene dyads as well as two cross‐conjugated SubPc‐tetraethynylethene (TEE) scaffolds. These TEEs containing two silyl‐protected alkyne units are potential building blocks for further acetylenic scaffolding. The work shows how the axial position is post‐functionalized in steps not involving a substitution reaction at the central boron atom, which is otherwise often used as the terminal step in axial functionalization of SubPcs.
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