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Synthesis and chiroptical properties of cylindrical macrocycles comprising two calix[3]aramide moieties

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Abstract

Calix[3]aramide-based cylindrical macrocycles were synthesized by the one-step amide coupling reaction of a monomer containing two meta-alkylaminobenzoic acid units linked by para-phenylene bridges. The major products included a meso-form and an enantiomeric pair, with stereochemistry derived from the direction of the amide bonds and their fixed conformation. Mirror-image ECD, VCD, and CPL spectra were observed in the enantiomeric pair and the absolute structure was determined by comparing measured and calculated ECD and VCD spectra.

Graphical abstract: Synthesis and chiroptical properties of cylindrical macrocycles comprising two calix[3]aramide moieties

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Publication details

The article was received on 17 Sep 2019, accepted on 22 Oct 2019 and first published on 23 Oct 2019


Article type: Paper
DOI: 10.1039/C9OB02022E
Org. Biomol. Chem., 2020, Advance Article

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    Synthesis and chiroptical properties of cylindrical macrocycles comprising two calix[3]aramide moieties

    Y. Saito, M. Satake, R. Mori, M. Okayasu, H. Masu, M. Tominaga, K. Katagiri, K. Yamaguchi, S. Kikkawa, H. Hikawa and I. Azumaya, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/C9OB02022E

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