Synthesis and Molecular Structure of a Copper Octaiodocorrole
| Autor: | Ivar Kristian Thomassen, Laura J. McCormick, Abhik Ghosh |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
VDP::Mathematics and natural science: 400::Chemistry: 440
010405 organic chemistry General Chemical Engineering Condensation chemistry.chemical_element Materials Engineering General Chemistry Chemical Engineering 010402 general chemistry 01 natural sciences Copper Combinatorial chemistry Article 0104 chemical sciences lcsh:Chemistry chemistry.chemical_compound lcsh:QD1-999 chemistry VDP::Matematikk og Naturvitenskap: 400::Kjemi: 440 Yield (chemistry) Electronic effect Trifluoroacetic acid Molecule Corrole Dichloromethane |
| Zdroj: | ACS omega, vol 3, iss 5 Thomassen, IK; Mccormick, LJ; & Ghosh, A. (2018). Synthesis and Molecular Structure of a Copper Octaiodocorrole. ACS Omega, 3(5), 5106-5110. doi: 10.1021/acsomega.8b00616. Lawrence Berkeley National Laboratory: Retrieved from: http://www.escholarship.org/uc/item/8576p12c ACS Omega, Vol 3, Iss 5, Pp 5106-5110 (2018) ACS Omega |
| ISSN: | 2470-1343 |
| Popis: | Source at https://doi.org/10.1021/acsomega.8b00616. Although rather delicate on account of their propensity to undergo deiodination, β-octaiodoporphyrinoids are of considerable interest as potential precursors to novel β-octasubstituted macrocycles. Presented herein are early results of our efforts to synthesize β-octaiodocorrole derivatives. Oxidative condensation of 3,4-diiodopyrrole and aromatic aldehydes failed to yield free-base octaiodocorroles. Treatment of copper meso-tris(p-cyanophenyl)corrole with N-iodosuccinimide and trifluoroacetic acid over several hours, however, yielded the desired β-octaiodinated product in ∼22% yield. Single-crystal X-ray structure determination of the product revealed a strongly saddled corrole macrocycle with metrical parameters very close to those of analogous Cu octabromocorrole complexes. The compound was also found to exhibit an exceptionally red-shifted Soret maximum (464 nm in dichloromethane), underscoring the remarkable electronic effect of β-octaiodo substitution. |
| Databáze: | OpenAIRE |
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