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Influence of Positional Isomerism on the Chiroptical Properties of Functional Aromatic Oligoamide Foldamers
Author(s) -
Moreno Kevin,
Merlet Eric,
McClenaghan Nathan,
Buffeteau Thierry,
Ferrand Yann,
Olivier Céline
Publication year - 2021
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.202100051
Subject(s) - chirality (physics) , chromophore , enantiopure drug , chemistry , substituent , enantiomer , quinoline , fluorophore , circular dichroism , luminescence , structural isomer , axial chirality , stereochemistry , photochemistry , crystallography , fluorescence , materials science , enantioselective synthesis , organic chemistry , physics , chiral symmetry breaking , optoelectronics , quantum mechanics , nambu–jona lasinio model , quark , catalysis
Abstract A series of functionalized quinoline‐based aromatic oligoamide foldamers were prepared in their two enantiomeric forms, comprising an enantiopure terminal camphanyl chiral inducer, which governed the adjacent (P‐/M‐) helical‐handedness. Hierarchical chirality transfer was further investigated in chromophore‐appended variants via a range of electronic and vibrational spectroscopic techniques, including circularly polarized luminescence, vibrational circular dichroism and fluorescence. Intense total and polarized photoluminescence (up to Φ lum =0.39, g lum =1.5×10 −3 ) was observed in the visible region from these modular multicomponent architectures and a significant influence of positional isomerism was evidenced. The optimal position of a fluorophore substituent on the quinoline hexamers was determined as being position 2 over position 6, as stronger chiroptical features were systematically observed with the 2‐positioned derivatives.