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


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 (fac-4 (fac-Ir(ppyCO2H)3 (ppy: 2-phenylpyridine)), fac-6 (fac-Ir(tpyCO2H)3 (tpy: 2-(4'-tolyl)pyridine)), and fac-13 (fac-Ir(mpiqCO2H)3 (mpiq: 1-(4'-methylphenyl)isoquinoline))) were converted into the diastereomers, Δ- and Λ-forms of fac-9 (from fac-6), fac-10 (from fac-4), fac-11 (from fac-6), and fac-14 (from fac-13), respectively, by the condensation with (1R,2R)-1,2-diaminocyclohexane or (1R,2R)-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 fac-10, fac-11, and fac-14 gave both enantiomers of the corresponding carboxylic acid derivatives in the optically pure forms, Δ-fac and Λ-fac-4, -6, and -13, respectively.

SUBMITTER: Kanbe A 

PROVIDER: S-EPMC10369494 | biostudies-literature | 2023 Jul

REPOSITORIES: biostudies-literature

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

Kanbe Azusa A   Yokoi Kenta K   Yamada Yasuyuki Y   Tsurui Makoto M   Kitagawa Yuichi Y   Hasegawa Yasuchika Y   Ogata Daiji D   Yuasa Junpei J   Aoki Shin S  

Inorganic chemistry 20230711 29


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 (<i>fac</i>-<b>4</b> (<i>fac</i>-Ir(ppyCO<sub>2</sub>H)<sub>3</sub> (ppy: 2-phenylpyridine)), <i>fac</i>-<b>6</b> (<i>fac</i>-Ir(tpyCO<sub>2</sub>H)<sub>3</sub> (tpy: 2-(4'-tolyl)pyridine)), and <i>fac</i>-<b>13</b> (<i>fac</i>-Ir(mpiqCO<sub>2</sub>H)<sub>3</sub> (mpiq: 1-(4'-methylphenyl)iso  ...[more]

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