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BF2- and PO2-smaragdyrins containing one five membered heterocycle such as pyrrole, thiophene and furan at one of the meso-position of corresponding 25-oxasmaragdyrins were synthesized by treating the appropriate mono meso-heterocycle substituted 25-oxasmaragdyrin with BF3.OEt2 and POCl3 respectively in CH2Cl2 under mild reaction conditions. All macrocycles were thoroughly characterized by HR-MS and 1D and 2D NMR spectroscopy. The presence of a five membered heterocycle in place of a six membered aryl group significantly alters the electronic properties of the smaragdyrin macrocycle as reflected in their spectral and electrochemical properties. The meso-pyrrole BF2-smaragdyrin was subjected to a Vilsmeier-Haack reaction to prepare meso-(α-formyl pyrrolyl) BF2-smaragdyrin which was subsequently used to prepare meso-(α-dipyrromethanyl pyrrolyl) BF2-smaragdyrin. The further use of meso-heterocycle substituted BF2- and PO2-oxasmaragdyrins was demonstrated by treating meso-pyrrolyl BF2-smaragdyrin with pentafluorobenzaldehyde in CHCl3 under mild acid catalysed conditions to afford an unusual dipyrromethanyl bridged BF2-smaragdyrin dyad which exhibits excellent photophysical properties. 相似文献
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