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Peer-reviewedCC BY 4.0Angewandte Chemie (International Ed. in English)

Molecular Recognition by Halogen Bonding With Atomic Precision in a Covalent Organic Cage

  • Pierre‐Antoine Dupin1
  • Jian Yang2
  • Elise Antonetti1
  • Bastien Chatelet3
  • Xavier Bugaut4
  • Jean‐Pierre Dutasta5
  • Paola Nava1
  • Anne‐Doriane Manick6
  • David Bardelang1
  • Alexandre Martinez1
6 affiliations
  1. 1Aix Marseille Univ, CNRS, Centrale Med, iSm2 Marseille France
  2. 2State Key Laboratory of Structural Chemistry Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences Fuzhou China
  3. 3IPCM, UMR 8232 Sorbonne Univ, CNRS Paris France
  4. 4LIMA, UMR 7042 Univ Strasbourg, Univ Haute Alsace, CNRS Strasbourg France
  5. 5LCH UMR 5182 CNRS, ENS de Lyon, Lyon 1 Université Lyon France
  6. 6Aix Marseille Univ, CNRS, ICR Marseille France
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Abstract

Halogen bonding (XB) is a recognition motif of increasing importance but it remains underused in solution. Embedding a single XB motif within a molecular capsule improves both its stability and interaction strength by finely tuning inward position and orientation. In this context, a new Covalent Organic Cage (COC) was prepared sequestering a polarized P‐Cl bond. This hemicryptophane carrying a haloazaphosphatrane moiety was found to bind dimethyl methylphosphonate (DMMP), a Sarin surrogate, by halogen bonding with atomic precision. Indeed, the same cage having the chlorine atom substituted by a hydrogen atom showed no detectable recognition. Such level of discrimination definitely establishes halogen bonding COC as a new generation of efficient receptors for molecular recognition.

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Cite

BibTeXRIS
BibTeX
@article{dupin2026molecular,
  title = {{Molecular Recognition by Halogen Bonding With Atomic Precision in a Covalent Organic Cage}},
  author = {Pierre‐Antoine Dupin and Jian Yang and Elise Antonetti and Bastien Chatelet and Xavier Bugaut and Jean‐Pierre Dutasta and Paola Nava and Anne‐Doriane Manick and David Bardelang and Alexandre Martinez},
  journal = {Angewandte Chemie (International Ed. in English)},
  year = {2026},
  month = sep,
  doi = {10.1002/anie.5640364},
  url = {https://doi.org/10.1002/anie.5640364},
  note = {CC BY 4.0},
}
RIS
TY  - JOUR
TI  - Molecular Recognition by Halogen Bonding With Atomic Precision in a Covalent Organic Cage
AU  - Pierre‐Antoine Dupin
AU  - Jian Yang
AU  - Elise Antonetti
AU  - Bastien Chatelet
AU  - Xavier Bugaut
AU  - Jean‐Pierre Dutasta
AU  - Paola Nava
AU  - Anne‐Doriane Manick
AU  - David Bardelang
AU  - Alexandre Martinez
PY  - 2026
DA  - 2026/09/27
JO  - Angewandte Chemie (International Ed. in English)
DO  - 10.1002/anie.5640364
UR  - https://doi.org/10.1002/anie.5640364
AB  - Halogen bonding (XB) is a recognition motif of increasing importance but it remains underused in solution. Embedding a single XB motif within a molecular capsule improves both its stability and interaction strength by finely tuning inward position and orientation. In this context, a new Covalent Organic Cage (COC) was prepared sequestering a polarized P‐Cl bond. This hemicryptophane carrying a haloazaphosphatrane moiety was found to bind dimethyl methylphosphonate (DMMP), a Sarin surrogate, by halogen bonding with atomic precision. Indeed, the same cage having the chlorine atom substituted by a hydrogen atom showed no detectable recognition. Such level of discrimination definitely establishes halogen bonding COC as a new generation of efficient receptors for molecular recognition.
SN  - 1433-7851
SN  - 1521-3773
ER  -