Control of Helix Screw‐Sense Preference in Dynamic Foldamers of meso Symmetry Built From Chiral Monomeric Units
ABSTRACT Meso oligoureas are dynamic hydrogen‐bonded foldamers capable of reversible helix polarity inversion but have so far been limited to symmetrical meso ‐cyclohexane‐1,2‐diamine monomeric units, limiting both sequence diversity and structural modification. Here, we report the synthesis and characterization of meso and “near‐ meso ” oligoureas assembled exclusively from chiral units, thereby expanding the accessible sequence space. Despite their overall symmetry, meso oligoureas display sequence‐dependent helix‐forming propensities. Controlled desymmetrization of terminal groups induces a preferred helix screw‐sense, while binding of achiral hydrogen‐bond acceptors reverses the directionality of the intramolecular hydrogen‐bonding network, leading to sequence‐dependent screw‐sense inversion. Structural, spectroscopic, and solution studies consistently support this stimulus‐responsive folding behavior.
Authors
- Sung Hyun Yoo (ORCID: https://orcid.org/0000-0002-9247-0434)
- Stéphanie Antunes (ORCID: https://orcid.org/0000-0003-3218-3924)
- Estelle Morvan (ORCID: https://orcid.org/0000-0003-4071-7885)
- Céline Douat (ORCID: https://orcid.org/0000-0003-2678-1047)
- Mégane Bornerie (ORCID: https://orcid.org/0000-0002-9115-9791)
- Antoine Hacıhasanoğlu
- Morgane Pasco (ORCID: https://orcid.org/0000-0002-1556-2802)
- Gilles Guichard (ORCID: https://orcid.org/0000-0002-2584-7502)
- Brice Kauffmann (ORCID: https://orcid.org/0000-0002-2932-3255)
- Noor‐ul H. Khan (ORCID: https://orcid.org/0000-0002-5204-5943)
- Philippe Carbonnière (ORCID: https://orcid.org/0000-0003-0305-3231)
- Bo Li (ORCID: https://orcid.org/0000-0002-4279-4596)
- Orlando Villegas Bello (ORCID: https://orcid.org/0000-0003-2153-5840)
- Jean‐Marc Sotiropoulos
Institutions
- Chonnam National University (KR)
- Centre National de la Recherche Scientifique (FR)
- Université de Pau et des Pays de l'Adour (FR)
- Université de Bordeaux (FR)
- Inserm (FR)
- Institut Européen de Chimie et Biologie (FR)
- Institut Polytechnique de Bordeaux (FR)
- Ludwig-Maximilians-Universität München (DE)
Publication Details
- Journal
- Angewandte Chemie International Edition
- Published
- 2026-10-07
- DOI
- https://doi.org/10.1002/anie.6601433
- Primary Topic
- Supramolecular Chemistry and Complexes
- Type
- article
- Field-Weighted Citation Impact
- 0.00