Spectroscopic study on enantiomeric Ni(II) complexes of porphyrin-porphyrin Troger's base and porphyrin-chlorin spiro-Troger's base derivatives supported by DFT calculations
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY（2024）
Abstract
The chiral properties of nickel(II) complexes of porphyrin-porphyrin Troger's base and porphyrin-chlorin spiroTroger's base with phenyl or 3-methoxyphenyl substitutions in their meso-positions were studied. Enantioseparation of racemic mixtures was investigated via high-performance liquid chromatography (HPLC) on an analytical ReproSil Chiral-NR column. The optimal conditions were utilized for a multimilligram scale isolation with a semipreparative column. The purity of the isolated enantiomers was determined by HPLC and UV-Vis spectroscopy. The absolute configurations of the isolated enantiomers were determined by evaluating the Cotton effect in electronic circular dichroism spectra. The determination was supported by TDDFT calculations, in which good agreement was achieved between the experimental and simulated spectra. The maximum molar ellipticity values, [theta 1 lambda max given in deg center dot cm2 center dot dmol 1, were [theta 1435 = 1.73 center dot 107 for phenyl spiroTB and [theta 1436 = 1.24 center dot 107 and [theta 1436 = 2.15 center dot 107 for 3-methoxyphenyl TB and spiroTB, respectively.
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Key words
Tro <spacing diaeresis>ger's Base,Spiro-Tro <spacing diaeresis>ger's Base,Enantioseparation,ECD,DFT Calculation,Absolute Configuration
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