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Related Experiment Videos

Bis-4,4'-biphenyl Ring Embedded Octaphyrin with Three Distinct Conformational Structures.

Sangya Chitranshi1, B Adinarayana1, Mainak Das1

  • 1National Institute of Science Education and Research (NISER), HBNI, Bhubaneswar, 752050, Odisha, India.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 15, 2019
PubMed
Summary

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Three carbaoctaphyrin structures were synthesized, revealing distinct conformations upon protonation and metalation. Local aromaticity in biphenyl units prevents overall macrocyclic aromaticity, leading to nonaromatic characteristics.

Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Carbaoctaphyrins are macrocyclic compounds with potential applications in various fields.
  • Understanding their conformational dynamics is crucial for designing novel functional materials.

Purpose of the Study:

  • To synthesize and characterize distinct conformational structures of carbaoctaphyrins.
  • To investigate the influence of protonation and metalation on their conformation and aromaticity.

Main Methods:

  • Incorporation of bis-4,4'-biphenyl units into the macrocyclic core.
  • Spectroscopic analyses (NMR, UV-Vis, etc.).
  • Theoretical calculations (DFT).
  • X-ray crystal structure determination.
Keywords:
carbaporphyrinoidscoordination chemistryexpanded porphyrinsnonaromaticityoctaphyrin

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Main Results:

  • Three distinct conformations were achieved: free-base (figure-eight), protonated (open-framework), and bis-Rh(I) metalated (singly twisted).
  • Local aromaticity of the biphenyl units dominated, resulting in nonaromatic characteristics for all structures.
  • Conformational changes were observed upon protonation and metalation.

Conclusions:

  • The conformational flexibility of carbaoctaphyrins can be controlled through external stimuli like protonation and metalation.
  • The dominance of local aromaticity over macrocyclic aromaticity influences their electronic properties.
  • These findings provide insights into the structure-property relationships of complex macrocyclic systems.