Silylethynyl Substituents as Porphyrin Protecting Groups for Solubilization and Selectivity Control

Silylethynyl substituents
are proposed as protecting groups for
porphyrin derivatives to enhance their solubility and enable regioselective
functionalization. After usage as protecting groups, silylethynyl
groups at the meso-positions can be efficiently removed
upon heating with aqueous H2SO4 in the presence
of a surfactant. This approach was applied to the preparation of unsymmetrically
β-substituted porphyrins and porphin–porphyrin oligomers,
which were inaccessible by conventional methods.

硅乙炔基取代基（silylethynyl substituents）被提议作为卟啉衍生物（porphyrin derivatives）的保护基，以增强其溶解性并实现区域选择性官能化。当作为保护基使用后，位于卟啉中位位点（meso-positions）的硅乙炔基可在表面活性剂存在下，通过与硫酸水溶液（aqueous H2SO4）共加热实现高效脱除。该策略已被应用于不对称β-取代卟啉以及卟吩-卟啉低聚物（porphin–porphyrin oligomers）的制备，这类产物是传统合成方法无法获取的。