One pot synthesis of unusual meso-dipyrrinyl corrole
| Autor: | Tejinder Kaur, Mangalampalli Ravikanth, Laxman Vamshi Krishna Kandala |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
Core-Modified Corroles
Absorption spectroscopy General Chemical Engineering One-pot synthesis Epoxidation 010402 general chemistry Photochemistry 01 natural sciences Absorption Catalysis Free-Base Corroles Metal chemistry.chemical_compound Complexes Metallocorroles Organic chemistry Molecule Noninnocent Ligands Corrole 010405 organic chemistry Chemistry General Chemistry Fluorescence Transition-Metal Centers 0104 chemical sciences visual_art visual_art.visual_art_medium Two-dimensional nuclear magnetic resonance spectroscopy Photophysical Properties |
| Zdroj: | RSC Advances. 7:19878-19884 |
| ISSN: | 2046-2069 |
| DOI: | 10.1039/c7ra02664a |
| Popis: | We have synthesized an unusual meso-dipyrrinyl corrole 1 in one pot reaction using 2 + 1 approach, by condensing pentafluorobenzaldehyde with meso-free dipyrromethane under TFA catalyzed reaction conditions followed by oxidation with a mild oxidant such as p-chloranil. The product was not obtained when we used other aldehydes such as p-nitrobenzaldehyde and p-cyanobenzaldehyde as well as when we changed the oxidant from p-chloranil to DDQ. We elucidated the molecular structure of 1 using detailed 1D and 2D NMR spectroscopy. The absorption spectrum showed typical Soret band and three Q-bands with slight shifts in the peak maxima compared to meso-free corrole. The meso-dipyrrinyl corrole was decently fluorescent and showed emission band at 678 nm. The preliminary study showed that the meso-free carbon of meso-dipyrrinyl corrole was sufficiently reactive for functionalization but the resulted functionalized meso-dipyrrinyl corroles were not stable to isolate. Our attempts to prepare metal complexes of meso-dipyrrinyl corroles remained unsuccessful because of the unstable nature of the resulted coordination complexes. |
| Databáze: | OpenAIRE |
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