Visible light-driven dehydrocoupling of thiols to disulfides and H2 evolution over PdS-decorated ZnIn2S4 composites

doi:10.1016/S1872-2067(23)64481-X

Abstract

Abstract:

The simultaneous utilization of photogenerated electrons and holes in one cooperative photoredox system for the dehydrocoupling of thiols into value-added disulfides and clean hydrogen (H₂) fuel meets the development criteria of green chemistry. Herein, we report the synthesis and application of cocatalyst PdS decorated ZnIn₂S₄ (PdS-ZIS) composites for photocatalytic coupling of thiols into disulfides and H₂ evolution under visible light irradiation. The superior photocatalytic performance over PdS-ZIS composites compared with blank ZIS is attributed to the function of PdS as oxidation cocatalyst, which dramatically promotes the separation and transfer of photogenerated charge carriers due to its excellent hole trapping ability. In-situ Fourier transform infrared spectra reveal the dynamic variation of reactants on the catalyst surface. Electron paramagnetic resonance technology confirms that sulfur-centered radicals are the key reaction intermediates in this coupling process. Moreover, the application of PdS-ZIS composites to the dehydrocoupling of various thiols with different substituent groups into the corresponding S-S coupling products has been demonstrated to be practicable. This work is expected to offer insights into the rational design of cocatalyst-decorated semiconductor photocatalysts with efficient utilization of photogenerated electrons and holes for the co-production of high-value chemicals and clean H₂ energy in a cooperative photoredox catalysis process.

Key words: Oxidation cocatalyst, ZnIn2S4, Photoredox reaction, Disulfide synthesis, Hydrogen evolution

Xiao-Juan Li, Ming-Yu Qi, Jing-Yu Li, Chang-Long Tan, Zi-Rong Tang, Yi-Jun Xu. Visible light-driven dehydrocoupling of thiols to disulfides and H₂ evolution over PdS-decorated ZnIn₂S₄ composites[J]. Chinese Journal of Catalysis, 2023, 51: 55-65.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(23)64481-X

https://www.cjcatal.com/EN/Y2023/V51/I8/55

Figures/Tables 8

Scheme 1. Comparison between previous works and this work for the dehydrocoupling of thiols to disulfides.

Fig. 1. (a) Systematic illustration of the synthetic procedure of the PdS decorated ZIS composites. (b) SEM image of ZIS. SEM (c), TEM (d), HRTEM (e) and high angle annular dark field (HAADF)-scanning TEM images and the element mapping results (f) of PdS-ZIS.

Fig. 2. XPS spectra of Zn 2p (a), In 3d (b) and S 2p (c) of ZIS and PdS-ZIS. (d) Pd 3d of PdS-ZIS. XRD patterns (e) and DRS spectra (f) of ZIS and PdS-ZIS composites containing different weight ratios of PdS.

Fig. 3. (a) Graphical representation of the photocatalytic selective dehydrogenation coupling of 4-MTP into 4-MPD and H2 evolution. (b) Photocatalytic activities of blank ZIS and x%PdS-ZIS (x = 0.5, 1, 3, 5). (c) Time-yield plots over 3%PdS-ZIS. (d) DRS spectrum of 3%PdS-ZIS and AQY of 4-MPD under different monochromatic lights. (e) Recycle tests over 3%PdS-ZIS. Reaction conditions of photocatalytic activity tests and recycle tests: 10 mg catalysts, 0.1 mmol 4-MTP, 10 mL MeCN, visible light, irradiation for 8 h.

Table 1 Photocatalytic dehydrogenation coupling of thiols with different substituents into corresponding disulfides and H2 evolution a.

Entry	Substrate	Yield of disulfide^b (%)	Selectivity of disulfide^c (%)	Disulfide generation rate (μmol/g_ZIS/h)	H₂ production rate (μmol/g_ZIS/h)	Carbon balance^d (%)	e^-/h^{+ e}
1	4-NH₂C₆H₄SH	98.5	99.4	615.7	607.1	99.6	0.99
2	4-NO₂C₆H₄SH	97.3	99.7	608.2	582.3	100	0.96
3	4-CH₃C₆H₄SH	80.2	99.5	501.2	493.7	99.5	0.99
4	4-ClC₆H₄SH	59.8	99.6	373.5	353.7	100	0.95
5	4-(CH₃)₃CC₆H₄SH	54.4	99.5	339.7	334.5	99.5	0.98
6	4-CF₃C₆H₄SH	48.4	99.4	302.8	276.3	99.4	0.91
7	4-FC₆H₄SH	51.9	99.8	324.3	293.4	99.8	0.90
8	4-CH₃CH₂C₆H₄SH	52.8	99.1	330.3	327.1	99.2	0.99
9	CH₃CH₂SH	98.5	99.9	615.5	607.1	99.9	0.99
10	HOOCCH₂SH	96.0	99.8	600.3	594.7	99.8	0.99

Fig. 4. Transient photocurrent response plots (a), EIS Nyquist plots (b), polarization curves (c), electron lifetime (d), PL spectra (e) and TRPL decay spectra (f) over ZIS and 3%PdS-ZIS.

Fig. 5. (a) Controlled tests for the photocatalytic coupling of 4-MTP with H2 evolution over 3%PdS-ZIS. Reaction conditions: 10 mg catalysts, 10 mL MeCN, 0.1 mmol 4-MTP, 0.2 mmol quenchers, Ar atmosphere, visible light, 8 h. (b) In-situ FTIR spectra over 3%PdS-ZIS. (c) EPR spectra of blank ZIS and 3%PdS-ZIS using DMPO as the trapping agents (dark and light). (d) Quantitative analysis of EPR spectrum for 3%PdS-ZIS.

Fig. 6. (a) Schematic diagram of the internal electric field formed between ZIS and PdS. (b) Systematic illustration of the photoredox catalyzed mechanism for dehydrogenation coupling of 4-MTP into 4-MPD and H2 evolution over PdS-ZIS photocatalyst (λ > 420 nm).

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Visible light-driven dehydrocoupling of thiols to disulfides and H₂ evolution over PdS-decorated ZnIn₂S₄ composites

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