Issue 39, 2023

The acceleration of BODIPY dye-sensitized photocatalytic hydrogen production in aqueous ascorbic acid solutions using alkyl-chain formed second coordination sphere effects

Abstract

BODIPY (boron-dipyrromethene) compounds are extensively utilized in various applications. Typically, their activity is modified by altering the functional groups at the α-, β-, and meso-positions of the substituents. However, no systematic information has been provided regarding the effects of substituted F- positions and hydrophobicity on the activity of BODIPY sensitizers in photosensitizing chemistry. Dyes (7a–7c) with different alkyl chain lengths were synthesized and compared with the unsubstituted compound 3 to discuss the effects of –F position substituents and the hydrophobicity of BODIPY dyes on photocatalytic activity. Density functional theory (DFT) calculations showed that –F-substitution induced an intramolecular charge transfer (ICT) effect, enhancing visible-light absorption. Longer alkyl chains provided a favourable second coordination sphere reaction environment for hydrogen production. Experimentally, dye 7c demonstrated the highest activity, with a hydrogen production rate of 496.5 μmol gcat−1 h−1, which is 3 times higher than that of 3, and a 9.6 times higher turnover frequency (TOF) than that of 3. The apparent quantum yield (AQY) at 650 nm was 1.4%. This study highlights the importance of –F position substitution and optimizing hydrophobicity to enhance the photocatalytic activity of metal-free organic dyes through the creation of a new second coordination sphere.

Graphical abstract: The acceleration of BODIPY dye-sensitized photocatalytic hydrogen production in aqueous ascorbic acid solutions using alkyl-chain formed second coordination sphere effects

Supplementary files

Article information

Article type
Paper
Submitted
23 Jun 2023
Accepted
06 Sep 2023
First published
06 Sep 2023

J. Mater. Chem. A, 2023,11, 21153-21160

Author version available

The acceleration of BODIPY dye-sensitized photocatalytic hydrogen production in aqueous ascorbic acid solutions using alkyl-chain formed second coordination sphere effects

X. Shen, M. Watanabe, J. T. Song, A. Takagaki, T. Abe, K. Tanaka and T. Ishihara, J. Mater. Chem. A, 2023, 11, 21153 DOI: 10.1039/D3TA03682K

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