Optical Resolution of Carboxylic Acid Derivatives of Homoleptic Cyclometalated Iridium(III) Complexes Via Diastereomers Formed with Chiral Auxiliaries

Overview

Journal Inorg Chem

Specialty Chemistry

Date 2023 Jul 11

PMID 37432912

Authors

Azusa Kanbe

Kenta Yokoi

Yasuyuki Yamada

Makoto Tsurui

Yuichi Kitagawa

Yasuchika Hasegawa

Daiji Ogata

Junpei Yuasa

Shin Aoki

Affiliations

Soon will be listed here.

Abstract

We report on a facile method for the optical resolution of cyclometalated iridium(III) (Ir(III)) complexes via diastereomers formed with chiral auxiliaries. The racemic carboxylic acids of Ir(III) complexes (- (-Ir(ppyCOH) (ppy: 2-phenylpyridine)), - (-Ir(tpyCOH) (tpy: 2-(4'-tolyl)pyridine)), and - (-Ir(mpiqCOH) (mpiq: 1-(4'-methylphenyl)isoquinoline))) were converted into the diastereomers, Δ- and Λ-forms of - (from -), - (from -), - (from -), and - (from -), respectively, by the condensation with (12)-1,2-diaminocyclohexane or (12)-2-aminocyclohexanol. The resulting diastereomers were separated by HPLC (with a nonchiral column) or silica gel column chromatography, and their absolute stereochemistry was determined by X-ray single-crystal structure analysis and CD (circular dichroism) spectra. Spectra of all diastereomers of the Ir(III) complexes are reported. Hydrolysis of the ester moieties of Δ- and Λ-forms of -, -, and - gave both enantiomers of the corresponding carboxylic acid derivatives in the optically pure forms, Δ- and Λ--, -, and -, respectively.

Citing Articles

Synthesis and Performance of Deep-Red Phosphorescent Iridium Complexes with Pyrone as an Auxiliary Ligand.

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PMID: 38999135 PMC: 11242998. DOI: 10.3390/molecules29133183.

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