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Directly linked hydroporphyrin dimers.

Ruisheng Xiong1, Anna I Arkhypchuk1, Daniel Kovacs1

  • 1Department of Chemistry, Ångström Laboratory, Uppsala University, Box 523, 75120 Uppsala, Sweden. eszter.borbas@kemi.uu.se.

Chemical Communications (Cambridge, England)
|February 10, 2016
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Summary

Researchers synthesized directly linked hydroporphyrin (chlorin) dimers using regioselective methods. This study details the creation and properties of novel chlorin dimers, advancing porphyrin chemistry.

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Photochemistry

Background:

  • Hydroporphyrins, specifically chlorins, are important macrocyclic compounds with diverse applications.
  • Directly linked porphyrin dimers offer unique photophysical and electronic properties.
  • Regioselective synthesis of complex linked macrocycles remains a synthetic challenge.

Purpose of the Study:

  • To develop a regioselective synthetic route to directly linked hydroporphyrin (chlorin) dimers.
  • To prepare versatile 15-borylated chlorin intermediates for further functionalization.
  • To investigate the photophysical and electrochemical properties of the synthesized chlorin dimers.

Main Methods:

  • Regioselective synthesis of chlorin dimers starting from bromochlorins.
  • Miyaura borylation to yield 15-borylated chlorin intermediates.
  • Suzuki coupling reactions to form meso-meso, meso-β-linked homo- and heterodimers.

Main Results:

  • Successful regioselective synthesis of directly linked hydroporphyrin (chlorin) dimers.
  • Efficient preparation of versatile 15-borylated chlorins in excellent yields.
  • Suzuki coupling enabled the formation of various meso-meso and meso-β linked homo- and heterodimers.

Conclusions:

  • A robust synthetic strategy for accessing directly linked chlorin dimers has been established.
  • The developed methods provide access to a range of novel chlorin dimer architectures.
  • The reported photophysical and electrochemical data provide insights into the properties of these linked systems.