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Conformational disorder in conjugated macrocycles impacts exciton behavior. Larger macrocyclic thiophenes deform into acyclic structures, hindering cyclic exciton formation.

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Area of Science:

  • Photophysics
  • Supramolecular Chemistry
  • Organic Electronics

Background:

  • Conformational disorder is crucial for exciton delocalization in conjugated macrocycles.
  • Cyclic excitons, fully delocalized over a cyclic framework, are influenced by molecular structure.
  • Understanding structure-property relationships in macrocycles is key for advanced materials.

Purpose of the Study:

  • Investigate the impact of ring size on the conformation and photophysical properties of macrocyclic thiophenes (CnT).
  • Determine how structural changes in macrocycles affect the formation of cyclic excitons.
  • Elucidate the relationship between molecular structure and exciton behavior in conjugated systems.

Main Methods:

  • Single-molecule fluorescence spectroscopy to measure modulation depth (M) and fluorescence intensity.
  • Molecular dynamics simulations to analyze conformational changes and torsional defects.
  • Analysis of fluorescence intensity trajectories and photon coincidence measurements.

Main Results:

  • Bimodal distributions in correlation plots of modulation depth and fluorescence intensity were observed for larger macrocycles.
  • Increased ring size leads to extremely congested linear structures in macrocyclic thiophenes.
  • Evidence of multiple acyclic chromophores in larger macrocycles due to complete deformation of circular structures.

Conclusions:

  • The ring size of macrocyclic thiophenes significantly influences their conformation and photophysical properties.
  • Larger macrocycles tend to deform into acyclic structures, preventing the formation of cyclic excitons.
  • Conformational disorder and structural deformation are critical factors governing exciton behavior in conjugated macrocycles.