Tekuri Chandra Sekhar, Singh Pargat, Nath Mahendra
Department of Chemistry, Faculty of Science, University of Delhi, Delhi 110 007, India.
Beilstein J Org Chem. 2023 Aug 11;19:1216-1224. doi: 10.3762/bjoc.19.89. eCollection 2023.
A facile one-pot four-component synthetic methodology is evolved to construct novel copper(II) benzo[]chromeno[2,3-]quinoxalinoporphyrins in good yields via a sequential reaction of copper(II) 2,3-diamino-5,10,15,20-tetraarylporphyrins, 2-hydroxynaphthalene-1,4-dione, aromatic aldehydes, and dimedone in the presence of a catalytic amount of trichloroacetic acid in chloroform at 65 °C. Further, the newly prepared copper(II) porphyrins were transformed to the corresponding free base and zinc(II) benzo[]chromeno[2,3-]quinoxalinoporphyrins under standard demetallation and zinc insertion conditions. The absorption and emission properties of the obtained porphyrins were investigated by using UV-visible and fluorescence spectroscopy. The preliminary photophysical results revealed a significant red-shift in their absorption and emission spectra as compared to the -tetrakis(4-methylphenyl)porphyrins due to the extended π-conjugation.
一种简便的一锅四组分合成方法被开发出来，通过在65℃下，在氯仿中，在催化量的三氯乙酸存在下，使2,3-二氨基-5,10,15,20-四芳基卟啉铜(II)、2-羟基萘-1,4-二酮、芳香醛和达米酮依次反应，以良好的产率构建新型苯并[]色烯并[2,3-]喹喔啉基卟啉铜(II)。此外，在标准的脱金属和锌插入条件下，新制备的卟啉铜(II)被转化为相应的游离碱和苯并[]色烯并[2,3-]喹喔啉基卟啉锌(II)。通过紫外可见光谱和荧光光谱研究了所得卟啉的吸收和发射性质。初步的光物理结果表明，由于π共轭的扩展，与四(4-甲基苯基)卟啉相比，它们的吸收和发射光谱有显著的红移。
