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Undecaphenylcorroles
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DOI：10.1021/ic301388e.png)
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摘要
En 中文
A first major study of undecaphenylcorrole (UPC) derivatives is presented. Three different Cu-UPC derivatives with different para substituents X (X = CF3, H, CH3) on the beta-aryl groups were synthesized via Suzuki-Miyaura coupling of Cu[Br8TPC] and the appropriate arylboronic acid. A single-crystal X-ray structure of the X = CF3 complex revealed a distinctly saddled macrocycle conformation with adjacent pyrrole rings tilted by similar to 60-66 degrees relative to one another (within the dipyrromethane units), which is somewhat higher than that observed for beta-unsubstituted Cu-TPC derivatives but slightly lower than that observed for Cu[Br8TPC] (similar to 70 degrees) derivatives. Electrochemical and electronic absorption measurements afforded some of the first comparative insights into meso versus beta substituent effects on the copper corrole core. The Soret maxima of the Cu-UPC complexes (similar to 440-445 nm), however, are comparable to those of Cu[Br8TPC] derivatives and are considerably red-shifted relative to Cu-TPC derivatives. Para substituents on the beta-phenyl groups were found to tune the redox potentials of copper corroles more effectively than those on meso-phenyl substituents, a somewhat surprising observation given that neither the HOMO nor LUMO has significant amplitudes at the beta-pyrrolic positions.
Keyword:
ELECTRONIC-ABSORPTION
PORPHYRINS
NONPLANAR
COMPLEXES
CORROLES
BONDS
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期刊
IF:
4.7
论文数:
4.9W
被引数:
10.5W
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