通过钯催化交叉偶联反应高效合成荧光香豆素和含磷香豆素型杂环化合物。

Faculty of Chemistry and Pharmacy, Sofia University "St. Kliment Ohridski", 1164 Sofia, Bulgaria.

Department of Inorganic Solid-State Chemistry, Saarland University, 66123 Saarbrücken, Germany.

Molecules. 2022 Nov 7;27(21):7649. doi: 10.3390/molecules27217649.

Quantum-chemical calculations on the spectral properties of some aryl substituted 3-phosphonocoumarins were performed, and the effect of the substituents in the aryl moiety was evaluated. The structures possessing promising fluorescent properties were successfully synthesized via Suzuki and Sonogashira cross-coupling. The synthetic protocol was also applied for the phosphorous chemoisomer of 3-phosphonocoumarin, 1,2-benzoxaphosphorin, and their carboxylate analogues. The optical properties of the arylated and alkynylated products were experimentally determined. The obtained quantum-chemical and experimental results give the possibility for a fine tuning of the optical properties of phosphorous-containing coumarin systems by altering the substituent at its C-6 position.

对一些芳基取代的 3-膦酰基香豆素的光谱性质进行了量子化学计算，并评估了芳基部分取代基的影响。通过 Suzuki 和 Sonogashira 交叉偶联成功合成了具有良好荧光性质的结构。该合成方案还应用于 3-膦酰基香豆素的磷化学异构体 1,2-苯并恶磷和它们的羧酸酯类似物。对芳基化和炔基化产物的光学性质进行了实验测定。获得的量子化学和实验结果为通过改变其 C-6 位置的取代基来精细调整含磷香豆素体系的光学性质提供了可能性。