Singh Dileep Kumar, Nath Mahendra
Department of Chemistry, University of Delhi, Delhi 110 007, India.
Beilstein J Org Chem. 2015 Aug 17;11:1434-40. doi: 10.3762/bjoc.11.155. eCollection 2015.
A novel series of β-triazoloporphyrin-xanthone conjugates and xanthone-bridged β-triazoloporphyrin dyads has been synthesized in moderate to good yields through Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction of copper(II) 2-azido-5,10,15,20-tetraphenylporphyrin or zinc(II) 2-azidomethyl-5,10,15,20-tetraphenylporphyrin with various alkyne derivatives of xanthones in DMF containing CuSO4 and ascorbic acid at 80 °C. Furthermore, these metalloporphyrins underwent demetalation under acidic conditions to afford the corresponding free-base porphyrins in good to excellent yields. After successful spectroscopic characterization, these porphyrins have been evaluated for their photophysical properties. The preliminary results revealed a bathochromic shift in the UV-vis and fluorescence spectra of these porphyrin-xanthone dyads.
通过在含有硫酸铜和抗坏血酸的N,N-二甲基甲酰胺中，于80℃下，使2-叠氮基-5,10,15,20-四苯基卟啉铜(II)或2-叠氮甲基-5,10,15,20-四苯基卟啉锌(II)与呫吨酮的各种炔烃衍生物发生铜(I)催化的惠斯根1,3-偶极环加成反应，已以中等至良好的产率合成了一系列新型的β-三唑卟啉-呫吨酮共轭物和呫吨酮桥连的β-三唑卟啉二元化合物。此外，这些金属卟啉在酸性条件下进行脱金属反应，以良好至优异的产率得到相应的游离碱卟啉。在成功进行光谱表征后，对这些卟啉的光物理性质进行了评估。初步结果表明，这些卟啉-呫吨酮二元化合物的紫外可见光谱和荧光光谱发生了红移。
