TY - JOUR
T1 - Direct Near Infrared Light–Activatable Phthalocyanine Catalysts
AU - Katsurayama, Yoshino
AU - Ikabata, Yasuhiro
AU - Maeda, Hajime
AU - Segi, Masahito
AU - Nakai, Hiromi
AU - Furuyama, Taniyuki
N1 - Funding Information:
This work was partly supported by JST PRESTO grant JPMJPR18TB, JSPS KAKENHI grant 18K19071, and the Kanazawa University SAKIGAKE Project 2020. Some of the calculations were performed at the Research Center for Computational Science (RCCS), Okazaki Research Facilities, National Institutes of Natural Sciences (NINS), while other calculations were performed at the Academic Center for Computing and Media Studies (ACCMS), Kyoto University.
Funding Information:
This work was partly supported by JST PRESTO grant JPMJPR18TB, JSPS KAKENHI grant 18K19071, and the Kanazawa University SAKIGAKE Project 2020. Some of the calculations were performed at the Research Center for Computational Science (RCCS), Okazaki Research Facilities, National Institutes of Natural Sciences (NINS), while other calculations were performed at the Academic Center for Computing and Media Studies (ACCMS), Kyoto University.
Publisher Copyright:
© 2021 Wiley-VCH GmbH
PY - 2022/1/10
Y1 - 2022/1/10
N2 - 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.
AB - 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.
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U2 - 10.1002/chem.202103223
DO - 10.1002/chem.202103223
M3 - Article
C2 - 34734432
AN - SCOPUS:85121341890
SN - 0947-6539
VL - 28
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 2
M1 - e202103223
ER -