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Self-Complementary Dimers Based on Zwitterionic Halogen Bond Donors.

Dana Kutzinski1, Raffaella Papagna1, Elric Engelage1

  • 1Fakultät für Chemie und Biochemie, Ruhr-Universität Bochum, Bochum, Germany.

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Summary
This summary is machine-generated.

Researchers developed novel zwitterionic halogen bond donors forming self-complementary homodimers. This breakthrough enables multipoint interactions, advancing crystal engineering and materials science.

Keywords:
halogen bondinghypervalent iodinemolecular recognitionself‐assemblyzwitterions

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Area of Science:

  • Supramolecular Chemistry
  • Crystal Engineering
  • Organic Chemistry

Background:

  • Halogen bonding is a key interaction in crystal engineering.
  • Multipoint halogen bonding motifs, especially self-complementary ones, are scarce.
  • Zwitterionic systems offer unique possibilities for designing halogen bond donors and acceptors.

Purpose of the Study:

  • To design and synthesize the first isolated homodimers based on a zwitterionic halogen bond donor.
  • To explore the potential of iodolium and sulfonate groups in creating self-complementary halogen bonding systems.
  • To investigate the structural and binding properties of these novel supramolecular assemblies.

Main Methods:

  • Synthesis of zwitterionic compounds featuring an iodolium core and a sulfonate group.
  • Crystallographic analysis to determine the structure of the isolated homodimers.
  • Spectroscopic and computational methods to characterize the halogen bonding interactions.

Main Results:

  • Successful formation of the first isolated homodimers utilizing a zwitterionic halogen bond donor.
  • Strongly bound dimers were observed with halogen bond distances up to 2.73 Å.
  • Optimization from carboxylate to sulfonate variants improved solubility and system stability.

Conclusions:

  • The developed zwitterionic iodolium-sulfonate motif represents a novel approach to self-complementary halogen bonding.
  • These homodimers demonstrate the potential for designing advanced materials with predictable multipoint interactions.
  • This work lays the foundation for developing new halogen-bonding-based linkers for various applications.