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Pyrrole-Based Zwitterionic π-Electronic Systems That Form Self-Assembled Dimers.

Hiromitsu Maeda1, Takayuki Okubo1, Yohei Haketa1

  • 1Department of Applied Chemistry, College of Life Sciences, Ritsumeikan University, Kusatsu, 525-8577, Japan.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 16, 2018
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Summary

New pyrrole-based zwitterions self-assemble into dimers through intermolecular hydrogen bonding. These dimers exist in equilibrium with monomers in DMSO, with dimerization influenced by concentration.

Keywords:
anion bindingarenesheterocyclesion pairspi-electronic moleculessolid-state assemblieszwitterions

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Zwitterionic π-electronic systems are of interest for their unique electronic and self-assembly properties.
  • Understanding intermolecular interactions is crucial for designing functional organic materials.

Purpose of the Study:

  • To synthesize novel pyrrole-based zwitterionic π-electronic systems.
  • To investigate the self-assembly behavior and intermolecular interactions of these zwitterions.
  • To determine the equilibrium between self-assembled dimers and monomers in solution.

Main Methods:

  • Synthesis of pyrrole-based zwitterions containing phenylcarboxylate (benzoate) and N-methyl pyridinium units.
  • Spectroscopic analyses (e.g., NMR, IR) to characterize the synthesized compounds.
  • Theoretical calculations to elucidate interaction mechanisms.
  • Concentration-dependent measurements in DMSO to study dimerization equilibrium.

Main Results:

  • Successful synthesis of pyrrole-based zwitterionic π-electronic systems.
  • Spectroscopic and theoretical data confirmed intermolecular hydrogen bonding between zwitterions.
  • Hydrogen bonding involves the pyrrole NH group, pyridinium, and benzoate ortho-CH moieties with a carboxylate anion, forming self-assembled dimers.
  • The self-assembled dimers exist in equilibrium with monomers in DMSO.
  • Dimerization ability is concentration-dependent.

Conclusions:

  • Pyrrole-based zwitterions can form self-assembled dimers via specific intermolecular hydrogen bonding.
  • The observed dimerization is reversible and exists in equilibrium with monomers in solution.
  • These findings provide insights into the supramolecular assembly of zwitterionic systems, relevant for molecular materials design.