دورية أكاديمية
Rapid one-pot synthesis of pyrrole-appended isocorroles.
| العنوان: | Rapid one-pot synthesis of pyrrole-appended isocorroles. |
|---|---|
| المؤلفون: | Larsen S; Department of Chemistry, UiT - The Arctic University of Norway, 9037 Tromsø, Norway. abhik.ghosh@uit.no., McCormick LJ, Ghosh A |
| المصدر: | Organic & biomolecular chemistry [Org Biomol Chem] 2019 Mar 20; Vol. 17 (12), pp. 3159-3166. |
| نوع المنشور: | Journal Article; Research Support, Non-U.S. Gov't |
| اللغة: | English |
| بيانات الدورية: | Publisher: Royal Society of Chemistry Country of Publication: England NLM ID: 101154995 Publication Model: Print Cited Medium: Internet ISSN: 1477-0539 (Electronic) Linking ISSN: 14770520 NLM ISO Abbreviation: Org Biomol Chem Subsets: PubMed not MEDLINE; MEDLINE |
| أسماء مطبوعة: | Original Publication: Cambridge, UK : Royal Society of Chemistry, c2003- |
| مستخلص: | Free-base meso-triarylcorroles have been found to undergo oxidative coupling with an excess of pyrrole in dichloromethane in the presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) affording 5/10-pyrrole-appended isocorroles in reasonable yields (35-60%) and in a matter of seconds. The free-base isocorrole ligands could all be complexed to copper with Cu(OAc)2·H2O in chloroform/methanol in 55-80% yields. Single-crystal X-ray structures of two of the new compounds (H2[5-pyr-TpOMePiC] and Cu[10-pyr-TpOMePiC]) revealed planar macrocycles with rms atomic displacements of only 0.02 and 0.06 Å relative to their respective best-fit C19N4 planes. Both free-base and Cu(ii)-complexed isocorroles exhibit richly featured UV-vis-NIR spectra with red/NIR absorption maxima at ∼650 nm and ∼725 nm for the free-bases and ∼800-850 nm for the copper complexes, suggesting potential applications in photodynamic therapy. Cyclic voltammetric analyses of five of the Cu complexes revealed fully reversible redox cycles with multiple oxidation and reduction features. |
| تواريخ الأحداث: | Date Created: 20190307 Date Completed: 20191125 Latest Revision: 20191125 |
| رمز التحديث: | 20231215 |
| DOI: | 10.1039/c9ob00168a |
| PMID: | 30838359 |
| قاعدة البيانات: | MEDLINE |
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