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A modular approach towards functionalized highly stable self-complementary quadruple hydrogen bonded systems.

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Area of Science:

  • Supramolecular Chemistry
  • Polymer Science
  • Organic Chemistry

Background:

  • Self-complementary quadruple hydrogen-bonding systems are crucial for supramolecular polymers.
  • Introducing multiple functionalities can expand their applications.

Purpose of the Study:

  • To develop a modular approach for introducing dual side chains into AADD-type self-complementary quadruple hydrogen-bonding systems.
  • To enhance the stability and versatility of these systems for supramolecular applications.

Main Methods:

  • Utilized dithiane-tethered ureidopyrimidinone as a reactive intermediate.
  • Attached closely aligned side chains by reacting with amines to form molecular duplexes.
  • Characterized the stability of the resulting duplexes in various solvents.

Main Results:

  • Successfully introduced two closely aligned side chains into AADD-type systems.
  • Formed highly stable molecular duplexes with strong binding constants (Kdim > 1.9 × 10^7 M^-1 in CDCl3 and Kdim > 10^5 in 10% DMSO-d6/CDCl3).
  • Demonstrated insensitivity to prototropy-related issues due to prototropic degeneracy.

Conclusions:

  • The novel modular approach enables efficient functionalization of self-complementary quadruple hydrogen-bonding systems.
  • The resulting duplexes exhibit exceptional stability in both non-polar and polar solvents.
  • Prototropic degeneracy enhances the robustness and applicability of these systems in supramolecular chemistry.