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분자활성 촉매반응 연구단
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Directing Foldamer Self-Assembly with a Cyclopropanoyl Cap

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Title
Directing Foldamer Self-Assembly with a Cyclopropanoyl Cap
Author(s)
Danim Lim; Hyunjoong Kim; Jintaek Gong; Jae-Hoon Eom; Eunyoung Yoon; Russell W. Driver; Mu-Hyun Baik; Hee-Seung Lee
Publication Date
2019-02
Journal
CHEMISTRY-A EUROPEAN JOURNAL, v.25, no.9, pp.2226 - 2233
Publisher
WILEY-V C H VERLAG GMBH
Abstract
The rational design of self-assembling organic materials is extremely challenging due to the difficulty in precisely predicting solid-state architectures from first principles, especially if synthons are conformationally flexible. A tractable model system to study self-assembly was constructed by appending cyclopropanoyl caps to the N termini of helical α/β-peptide foldamers, designed to form both N−H⋅⋅⋅O and C α −H⋅⋅⋅O hydrogen bonds, which then rapidly self-assembled to form foldectures (foldamer architectures). Through a combined analytical and computational investigation, cyclopropanoyl capping was observed to markedly enhance self-assembly in recalcitrant substrates and direct the formation of a single intermolecular N−H⋅⋅⋅O/C α −H⋅⋅⋅O bonding motif in single crystals, regardless of peptide sequence or foldamer conformation. In contrast to previous studies, foldamer constituents of single crystals and foldectures assumed different secondary structures and different molecular packing modes, despite a conserved N−H⋅⋅⋅O/C α −H⋅⋅⋅O bonding motif. DFT calculations validated the experimental results by showing that the N−H⋅⋅⋅O/C α −H⋅⋅⋅O interaction created by the cap was sufficiently attractive to influence self-assembly. This versatile strategy to harness secondary noncovalent interactions in the rational design of self-assembling organic materials will allow for the exploration of new substrates and speed up the development of novel applications within this increasingly important class of materials. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
URI
https://pr.ibs.re.kr/handle/8788114/5723
ISSN
0947-6539
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
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