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- Title
Porphyrin‐Based Air‐Stable Helical Radicals.
- Authors
Kato, Kenichi; Osuka, Atsuhiro; Furukawa, Ko; Mori, Tadashi
- Abstract
Abstract: Stable helical radicals are promising multi‐functional molecules in light of intriguing magnetic and chiroptical properties. Attempts were made to extend diphenylmethyl‐fused NiII porphyrin radical to helical system as the first air‐stable organic neutral helical radicals. Intramolecular Pd‐catalyzed twofold C−H arylation of methyl‐ or methoxy‐introduced <italic>meso</italic>‐diphenylmethyl NiII porphyrins gave a mixture of the target and rearranged radicals. Oxidative fusion reaction of <italic>meso</italic>‐(bis(1‐naphthyl)methyl) NiII porphyrins provided doubly fused NiII porphyrin radicals. One of the helical radicals was separated into enantiomers that showed mirror‐image circular dichroism (CD) spectra up to 1300 nm. The helical dinaphthylmethyl‐fused NiII porphyrin radical displayed solid‐state magnetic property mostly arising from monomeric radicals, different from the parent diphenylmethyl‐fused NiII porphyrin radical that showed antiferromagnetic coupling due to π‐stacked pairing.
- Subjects
PORPHYRINS; SOLVENTS; SPECTROMETERS; CYCLIC voltammetry; ETHYLENE dibromide
- Publication
Chemistry - A European Journal, 2018, Vol 24, Issue 3, p572
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201705291