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Visible Light-Driven Suzuki-Miyaura Reactions by Self-Supported Pd Nanocatalysts in the Formation of Stille Coupling-Based Photoactive Microporous Organic Polymers

Abstract

Stille coupling was applied to synthesize microporous organic polymers (MOPs). Metallic Pd was in situ self-supported during the networking of 1,3,6,8-tetrabromopyrene with 1,4-bis(tributylstannyl)benzene to form Stille coupling-based MOP(St-MOP)@Pd. The size of St-MOP particles and the amount of metallic Pd in the St-MOP@Pd depended on the amount of a Pd catalyst. As the amount of a Pd catalyst increased, the size of St-MOP particles decreased with an increase of metallic Pd, due to the increased St-MOP nuclei in the early growth stage of St-MOP. The St-MOP bearing pyrenes showed absorption and emission of visible light and the St-MOP@Pd showed excellent catalytic performance in the visible light-driven Suzuki-Miyaura coupling. The optimal St-MOP@Pd-2 (0.14 mol% Pd) showed a TON of 657 and a TOF of 219 h-1 in the visible light-driven Suzuki-Miyaura coupling of 1-acetyl-4-bromobenzene and phenyl boronic acid at 25oC. The optimal amount of St-MOP and metallic Pd in the St-MOP@Pd was critical to achieve excellent catalytic performance. The overall photocatalytic principles of St-MOP@Pd were rationalized by computational simulation.

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Supplementary files

Article information


Submitted
15 May 2020
Accepted
29 Jun 2020
First published
29 Jun 2020

Catal. Sci. Technol., 2020, Accepted Manuscript
Article type
Paper

Visible Light-Driven Suzuki-Miyaura Reactions by Self-Supported Pd Nanocatalysts in the Formation of Stille Coupling-Based Photoactive Microporous Organic Polymers

S. U. Son, S. H. Ryu, S. J. Choi, J. H. Seon, B. Jo, S. M. Lee, H. J. Kim, Y. Ko, K. C. Ko and T. K. Ahn, Catal. Sci. Technol., 2020, Accepted Manuscript , DOI: 10.1039/D0CY00997K

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