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Directing the Self-Assembly Behaviour of Porphyrin-Based Supramolecular Systems.

Rob van der Weegen1, Abraham J P Teunissen1, E W Meijer1

  • 1Laboratory of Macromolecular and Organic Chemistry, Institute for Complex Molecular Systems, Eindhoven University of Technology, P.O. Box 513, 5600 MB, Eindhoven, The Netherlands.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|January 24, 2017
PubMed
Summary

Small changes in porphyrin molecular structure dictate self-assembly into H- or J-aggregates. This study reveals parallel assembly pathways and distinct aggregation mechanisms, highlighting the sensitivity of supramolecular structures to molecular design.

Keywords:
pathway complexitypolymerizationporphyrinsself-assemblysupramolecular chemistry

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Physical Chemistry

Background:

  • Porphyrins are versatile molecules with applications in catalysis, sensing, and medicine.
  • Controlling the self-assembly of porphyrins into specific aggregates (H- or J-aggregates) is crucial for tuning their optical and electronic properties.
  • The influence of molecular architecture on porphyrin aggregation pathways remains an active area of research.

Purpose of the Study:

  • To investigate the self-assembly behavior of tetra-amidated porphyrins with varying solubilizing wedges in dilute solutions.
  • To elucidate the thermodynamic and kinetic mechanisms governing the formation of H- and J-aggregates.
  • To understand how subtle changes in molecular structure affect the balance between different aggregate types.

Main Methods:

  • Synthesis of a library of tetra-amidated porphyrins with diverse solubilizing wedges.
  • Spectroscopic analysis using Circular Dichroism (CD) and UV/Vis absorption spectroscopy.
  • Thermodynamic and kinetic studies to determine aggregation mechanisms and pathways.

Main Results:

  • Porphyrins formed co-facial H-aggregates, slip-stacked J-aggregates, or mixtures thereof, depending on the solubilizing wedge.
  • J-aggregate formation followed an isodesmic mechanism, while H-aggregate formation proceeded via a cooperative mechanism.
  • Both H- and J-aggregate formation occurred via parallel pathways, competing for monomers.
  • Even porphyrins favoring H-aggregates thermodynamically showed evidence of a competing J-aggregate pathway kinetically.

Conclusions:

  • The balance between H- and J-aggregate formation is highly sensitive to minor modifications in the solubilizing wedge architecture.
  • Understanding these assembly pathways provides critical insights for designing porphyrin-based materials with tailored properties.
  • The study demonstrates the complexity of supramolecular assembly, involving parallel pathways and distinct kinetic/thermodynamic controls.