title: Locking Interconversion of Aromatic Oligoamide Foldamers by Intramolecular Side-chain Crosslinking: toward Absolute Control of Helicity in Synthetic Aromatic Foldamers.
abstract: A series of foldamers of 8-amino-2-quinoline carboxylic acid were stapled by intramolecular ring-closing olefin metathesis to generate the constrained aromatic foldamers with varying lengths of hydrocarbon side-chains. Investigations clearly revealed that the side-chain crosslinkers are capable of completely locking the interconversions of the stapled aromatic foldamers over a wide range of temperatures in CDCl3, even in C2D2Cl4. Hence, the stapled foldamers with the short hydrocarbon crosslinker can be easily separated by silica-gel chromatography to generate foldamers with stable, absolute one-handed helicity. But the stapled foldamer with the longer crosslinker is inseparable even by chiral HPLC presumably due to the fortuitous identical polarity of the diastereomer.
authors.affiliation: Key Laboratory of Theoretical and Computational Photochemistry, and Key Laboratory of Radiopharmaceuticals, Ministry of Education, College of Chemistry, Beijing Normal University, Beijing, 100875, P. R. China.
authors.forename: Lu
authors.initials: L
authors.lastname: Zheng
authors.affiliation: Key Laboratory of Theoretical and Computational Photochemistry, and Key Laboratory of Radiopharmaceuticals, Ministry of Education, College of Chemistry, Beijing Normal University, Beijing, 100875, P. R. China.
authors.forename: Chengyuan
authors.initials: C
authors.lastname: Yu
authors.affiliation: Key Laboratory of Theoretical and Computational Photochemistry, and Key Laboratory of Radiopharmaceuticals, Ministry of Education, College of Chemistry, Beijing Normal University, Beijing, 100875, P. R. China.
authors.forename: Yulin
authors.initials: Y
authors.lastname: Zhan
authors.affiliation: Key Laboratory of Theoretical and Computational Photochemistry, and Key Laboratory of Radiopharmaceuticals, Ministry of Education, College of Chemistry, Beijing Normal University, Beijing, 100875, P. R. China.
authors.forename: Xuebin
authors.initials: X
authors.lastname: Deng
authors.affiliation: Key Laboratory of Theoretical and Computational Photochemistry, and Key Laboratory of Radiopharmaceuticals, Ministry of Education, College of Chemistry, Beijing Normal University, Beijing, 100875, P. R. China.
authors.forename: Ying
authors.initials: Y
authors.lastname: Wang
authors.affiliation: Key Laboratory of Theoretical and Computational Photochemistry, and Key Laboratory of Radiopharmaceuticals, Ministry of Education, College of Chemistry, Beijing Normal University, Beijing, 100875, P. R. China.
authors.forename: Hua
authors.identifier: http://orcid.org/0000-0002-9917-2683
authors.initials: H
authors.lastname: Jiang
keywords: aromatic foldamers; interconversion; one-handed helicity; ring-closing olefin metathesis; side-chain crosslinking