Synthesis and molecular structure of a copper octaiodocorrole

Thomassen, Ivar K., Mccormick, Laura J. and Ghosh, Abhik (2018) Synthesis and molecular structure of a copper octaiodocorrole. ACS Omega, 3 (5), 5106-5110. (doi:10.1021/acsomega.8b00616).

Record type: Article

Abstract

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.

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