Direct Near Infrared Light–Activatable Phthalocyanine Catalysts

Yoshino Katsurayama, Yasuhiro Ikabata, Hajime Maeda, Masahito Segi, Hiromi Nakai, Taniyuki Furuyama*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

The high penetration of near-infrared (NIR) light makes it effective for use in selective reactions under light-shielded conditions, such as in sealed reactors and deep tissues. Herein, we report the development of phthalocyanine catalysts directly activated by NIR light to transform small organic molecules. The desired photocatalytic properties were achieved in the phthalocyanines by introducing the appropriate peripheral substituents and central metal. These phthalocyanine photocatalysts promote cross-dehydrogenative-coupling (CDC) under irradiation with 810 nm NIR light. The choice of solvent is important, and a mixture of a reaction-accelerating (pyridine) and -decelerating (methanol) solvents was particularly effective. Moreover, we demonstrate photoreactions under visible-light-shielded conditions through the transmission of NIR light. A combined experimental and computational mechanistic analysis revealed that this NIR reaction does not involve a photoredox-type mechanism with electron transfer, but instead a singlet-oxygen-mediated mechanism with energy transfer.

Original languageEnglish
Article numbere202103223
JournalChemistry - A European Journal
Volume28
Issue number2
DOIs
Publication statusPublished - 2022 Jan 10

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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