Synthesis and chiroptical properties of cylindrical macrocycles comprising two calix[3]aramide moieties†
Misaki
Okayasu, 
a
Hyuma
Masu,
b
Masahide
Tominaga,
c
Kosuke
Katagiri,
d
Kentaro
Yamaguchi,
c
Shoko
Kikkawa,
a
Hidemasa
Hikawa
a
and
Isao
Azumaya
*a
a
Hyuma
Masu,
b
Masahide
Tominaga,
c
Kosuke
Katagiri,
d
Kentaro
Yamaguchi,
c
Shoko
Kikkawa,
a
Hidemasa
Hikawa
a
and
Isao
Azumaya
*a
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](/en/Image/Get?imageInfo.ImageType=GA&imageInfo.ImageIdentifier.ManuscriptID=C9OB02022E&imageInfo.ImageIdentifier.Year=2020)
- This article is part of the themed collection: Supramolecular chemistry in OBC
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