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Structure‐Dependent Guest Recognition with Flexible Ferrocene‐Based Aromatic Oligoamide β‐Sheet Mimics
Author(s) -
Liu YaZhou,
Wang Hu,
Chan ChiehKai,
Mu Xiao,
Robeyns Koen,
Wang ChengChung,
Singleton Michael L.
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201904719
Subject(s) - ferrocene , molecular recognition , molecule , chemistry , aromaticity , modular design , selectivity , materials science , organic chemistry , computer science , catalysis , electrode , electrochemistry , operating system
A series of aromatic oligoamides incorporating an inherently flexible ferrocene dicarboxylic acid unit was synthesized. Solid state, solution, and computational studies on these systems indicated that the aromatic strands can adopt a syn parallel stacked conformation. This results in modular β‐sheet‐like molecular clefts that display structure‐dependent recognition of small polar molecules. NMR and theoretical studies of the host–guest interaction support an in cleft binding mode and allowed the selectivity of the oligomers to be rationalized on the basis of minor changes in functional‐group presentation on the edge of the aromatic strands.