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. 2020 Jun 22;59(26):10363-10367.
doi: 10.1002/anie.202001231. Epub 2020 Apr 30.

Consecutive Charging of a Perylene Bisimide Dye by Multistep Low-Energy Solar-Light-Induced Electron Transfer Towards H2 Evolution

Yucheng Xu  1 , Jiaxin Zheng  1 , Joachim O Lindner  2 , Xinbo Wen  1 , Nianqiang Jiang  1 , Zhicheng Hu  1 , Linlin Liu  1 , Fei Huang  1 , Frank Würthner  2 , Zengqi Xie  1
Affiliations

Consecutive Charging of a Perylene Bisimide Dye by Multistep Low-Energy Solar-Light-Induced Electron Transfer Towards H2 Evolution

Yucheng Xu et al. Angew Chem Int Ed Engl. .

Abstract

A photocatalytic system containing a perylene bisimide (PBI) dye as a photosensitizer anchored to titanium dioxide (TiO2 ) nanoparticles through carboxyl groups was constructed. Under solar-light irradiation in the presence of sacrificial triethanolamine (TEOA) in neutral and basic conditions (pH 8.5), a reaction cascade is initiated in which the PBI molecule first absorbs green light, giving the formation of a stable radical anion (PBI.- ), which in a second step absorbs near-infrared light, forming a stable PBI dianion (PBI2- ). Finally, the dianion absorbs red light and injects an electron into the TiO2 nanoparticle that is coated with platinum co-catalyst for hydrogen evolution. The hydrogen evolution rates (HERs) are as high as 1216 and 1022 μmol h-1 g-1 with simulated sunlight irradiation in neutral and basic conditions, respectively.

Keywords: electron transfer; hydrogen evolution; nanoparticles; perylene bisimides; solar energy.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Illustration of the charging processes of cp‐PBI by multistep photo‐induced electron transfer, and the subsequent charge transfer from cp‐PBI2− to TiO2 nanoparticle for hydrogen evolution. The positions of the energy levels for radical anionic and dianionic states are estimated based on the CV results since they cannot be directly derived from our experiments. NHE=normal hydrogen electrode.
Figure 2
Figure 2
a) Chemical structure of cp‐PBI. b) UV/Vis absorption spectra of cp‐PBI (10−5  m) in deoxygenated DMSO in the presence of TEOA (0.1 m) in the dark, and its anion forms (cp‐PBI.− and cp‐PBI2−) prepared by light irradiation in the presence of TEOA (0.1 m). Inset in (b) shows the photographs of the solutions in cells.
Figure 3
Figure 3
a) Photocatalytic activity of Pt/TiO2/cp‐PBI for hydrogen evolution in 5 hours. Conditions: 20 mg of sample in 50 mL of TEOA (0.1 m) aqueous solution. A 300 W Xe lamp (AM 1.5 filter, 100 mW cm−1−2) was used as a light source. b) Long term experiment of Pt/TiO2/cp‐PBI using TEOA (0.1 m) as sacrificial agent (pH 7.0). Samples were degassed every five hours. c) Photograph of the reaction mixture of Pt/TiO2/cp‐PBI during hydrogen evolution experiment.
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