Supramolecular Capsules: Strong versus Weak Chalcogen Bonding

DOI Web Site Web Site Web Site 被引用文献11件
  • Leslie‐Joana Riwar
    Laboratorium für Organische Chemie ETH Zurich Vladimir-Prelog-Weg 3 8093 Zurich Switzerland
  • Nils Trapp
    Laboratorium für Organische Chemie ETH Zurich Vladimir-Prelog-Weg 3 8093 Zurich Switzerland
  • Katharina Root
    Laboratorium für Organische Chemie ETH Zurich Vladimir-Prelog-Weg 3 8093 Zurich Switzerland
  • Renato Zenobi
    Laboratorium für Organische Chemie ETH Zurich Vladimir-Prelog-Weg 3 8093 Zurich Switzerland
  • François Diederich
    Laboratorium für Organische Chemie ETH Zurich Vladimir-Prelog-Weg 3 8093 Zurich Switzerland

書誌事項

公開日
2018-11-27
権利情報
  • http://onlinelibrary.wiley.com/termsAndConditions#vor
DOI
  • 10.1002/anie.201812095
公開者
Wiley

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説明

<jats:title>Abstract</jats:title><jats:p>Resorcin[4]arene cavitands containing either 2,1,3‐benzotelluradiazole or 2,1,3‐benzothiadiazole motifs were dimerized to supramolecular capsules by chalcogen bonding. Their respective behavior varied depending on the interaction strength of the chalcogen bonds with Te forming strong interactions and S weak interactions. The tremendous strength of multiple 2Te–2N square interactions led to formation of a chalcogen‐bonded dimeric capsule in all solvents, as shown by X‐ray crystal structures with 16 short Te⋅⋅⋅N distances (≤2.9 Å) and confirmed by native electrospray ionization mass spectrometry (ESI‐MS). With the S cavitand, solvent‐dependent crystallization resulted in different arrangements: either a shifted 2S–2N square‐bonded capsule or an interlocked 1D polymer with an infinite π–π stacking array. The association constant to form the dimeric capsule in [D<jats:sub>8</jats:sub>]THF at 283 K, solely based on weak 2S–2N square interactions, was determined as <jats:italic>K</jats:italic><jats:sub>a</jats:sub>=786 <jats:sc>m</jats:sc><jats:sup>−1</jats:sup>.</jats:p>

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