Synthesis and chiroptical properties of cylindrical macrocycles comprising two calix[3]aramide moieties. Issue 2 (4th November 2019)

• Record Type: Journal Article
• Authors: Saito, Yuuki; Satake, Misa; Mori, Ryuichi; Okayasu, Misaki; Masu, Hyuma; Tominaga, Masahide; Katagiri, Kosuke; Yamaguchi, Kentaro; Kikkawa, Shoko; Hikawa, Hidemasa; Azumaya, Isao
• Is Part Of: Organic & biomolecular chemistry. Volume 18:Issue 2(2019)
• Page Start: 230
• Page End: 236
• Publication Date: 2019-11-04
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob02022e
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Novel chiral macrocyclic aromatic amides of medium molecular weight were synthesized by the one-step amide coupling of a bis(alkylamino)terphenyl diacid as monomer. 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.