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Chiral V‐shaped Pyrenes: Hexagonal Packing, Superhelix, and Amplified Chiroptical Performance
Author(s) -
Hu Song,
Hu Liangyu,
Zhu Xuefeng,
Wang Yuan,
Liu Minghua
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202107842
Subject(s) - circular dichroism , supramolecular chemistry , pyrene , intramolecular force , cyclohexane , crystallography , superhelix , supramolecular chirality , chemistry , molecule , self assembly , hexagonal crystal system , excimer , materials science , stereochemistry , fluorescence , nanotechnology , dna , crystal structure , organic chemistry , optics , biochemistry , dna replication , dna supercoil , physics
Here, we designed symmetric and dissymmetric chiral V‐shaped pyrenes by linking achiral pyrenes to trans ‐1,2‐cyclohexane diamine scaffolds with varied spacers to investigate their circular dichroism (CD) and circularly polarized excimer emission (CPEE). In molecular solution, the symmetric V‐shaped molecules ( P1 , P2 , P3 ) displayed spacer‐dependent CD and CPEE originating from the intramolecular excimers while the dissymmetric V‐shaped B was silent in CD and CPEE. Upon self‐assembly, the chiral V‐shaped conformation guided a helical hexagonal packing. Notably, P1 self‐assembled into delicate superhelices with optimum chiroptical activities and the largest g CD for pyrene derivatives to date. The dissymmetric B formed two distinct hexagonal aggregates as twists and rectangular nanotubes with greatly amplified CPEE. This work demonstrates unprecedented hexagonal superhelices from chiral V‐shaped scaffolds and provides a deep insight into the relationship between molecular conformation, supramolecular architectures, and their chiroptical performance.