Benzimidazole-based covalent organic framework embedding single-atom Pt sites for visible-light-driven photocatalytic hydrogen evolution

doi:10.1016/S1872-2067(23)64422-5

Abstract

Abstract:

Visible-light-driven photocatalytic hydrogen evolution reaction (HER) over a semiconductor provides an effective avenue to produce renewable clean energy and alleviate energy and environmental crises. However, the HER efficiency is still limited by the sluggish electron transfer process. Herein, a highly active covalent organic framework (COF) was constructed from the unusual benzimidazole monomer in a microwave-assisted solvothermal pathway. With single-atom Pt sites as cocatalyst, the catalyst exhibited an HER rate up to 115 mmol g^-1 h^-1 and a high turnover frequency of 4475.1 h^-1 under visible-light irradiation. The above performance relied on the combination of benzimidazole moieties and COF framework, which, on the one hand, stabilized photogenerated electrons to prolong the electron lifetime, and on the other hand provided a strong host-guest interaction that resulted in the creation of single-atom Pt sites and the acceleration of the electron-transfer to the active sites for proton reduction. This work demonstrates the perspective of electron stabilization and interfacial charge transfer avenue construction in the HER process, which can be reached by a molecular-level design of COF-based organic semiconductors by using structural and functional diverse asymmetric building blocks.

Key words: Covalent organic framework, Photocatalysis, Hydrogen evolution reaction, Single-atom catalysis, Renewable energy

Fangpei Ma, Qingping Tang, Shibo Xi, Guoqing Li, Tao Chen, Xingchen Ling, Yinong Lyu, Yunpeng Liu, Xiaolong Zhao, Yu Zhou, Jun Wang. Benzimidazole-based covalent organic framework embedding single-atom Pt sites for visible-light-driven photocatalytic hydrogen evolution[J]. Chinese Journal of Catalysis, 2023, 48: 137-149.

×
share this article

Add to citation manager EndNote|Ris|BibTeX

URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(23)64422-5

https://www.cjcatal.com/EN/Y2023/V48/I5/137

Figures/Tables 4

Fig. 1. (a) Schematic illustration of the molecular structure for PABZ-Tp with the synthetic procedure. (b) Lattice structure at the top and side view (yellow: carbon; white: hydrogen; blue: nitrogen; red: oxygen; red: sulfur). (c) Experimentally observed (red) and Pawley refined (black) PXRD patterns with their refinement difference (gray), the reflections and the simulated one (blue) for ideal AA-stacking mode. (d) Solid-state 13C CP-MAS NMR spectrum of PABZ-Tp. (e) N2 sorption isotherms and the corresponding pore size distribution profiles of PABZ-Tp; HR-TEM (f) and Fourier transform (FFT) (g) images. HAADF-STEM (h) and the corresponding elemental mapping (i-k) images for C, N, and O atoms. Scale bars: f: 5 nm; g: 1 nm; h-k: 100 nm.

Fig. 2. UV-vis diffuse reflection absorption spectra (a), energy band gap (b) determined from the Kubelka-Munk-transformed reflectance spectra, transient photocurrent responses (c), electrochemical impedance spectra (d), steady-state Photoluminescence spectra (e), and time-resolved fluorescence decay spectra (f) of PABZ-Tp, PABZ-Tp-A, and Tp-BD.

Fig. 3. (a) Time-resolved HER activity of PABZ-Tp, PABZ-Tp-A, and Tp-BD. (b) TOF comparisons of PABZ-Tp (red pentastar) and other representative photocatalysts (entries 1-21 in Table S14; the circle is COF-based photocatalyst, the square is TiO2-based photocatalyst, the pentagon is MOF-based photocatalyst, and the diamond is amorphous polymer photocatalyst). (c) Cycling HER behavior of PABZ-Tp. (d) Wavelength-dependent AQE of PABZ-Tp. (e) The photocatalytic H2 evolution rate of PABZ-Tp, PABZ-Tp-A, and Tp-BD in the absence of Pt additive. (f) HR-TEM, AC HAADF-STEM images of Pt/PABZ-Tp, and corresponding electron lattice diffraction diagram; Pt L3-edge X-ray absorption near-edge structure (g) and corresponding k3-weighted Fourier transform spectra (h) at R space of Pt/PABZ-Tp, PtO2, and Pt foil.

Fig. 4. (a) TPV curves of PABZ-Tp and Tp-BD. (b) The radical anion pathway (solid arrow) and radical cationic pathway (dotted arrows) after photoexcitation of PABZ-Tp and Tp-BD, with the difference of the adiabatic stabilization energy of the radical cation and anion state relative to the neutral state for the optimized representative fragment of PABZ-Tp and Tp-BD. Charge distribution and dipole moment of the radical anion state for the optimized representative fragment of PABZ-Tp (c) and Tp-BD (d). C gray, H white, O red, N blue.

References

[1]	Z. Wang, C. Li, K. Domen, Chem. Soc. Rev., 2019, 48, 2109-2125.
[2]	L. H. Lin, Z. Y. Lin, J. Zhang, X. Cai, W. Lin, Z. Y. Yu, X. C. Wang, Nat. Catal., 2020, 3, 649-655.
[3]	H. Nishiyama, T. Yamada, M. Nakabayashi, Y. Maehara, M. Yamaguchi, Y. Kuromiya, Y. Nagatsuma, H. Tokudome, S. Akiyama, T. Watanabe, R. Narushima, S. Okunaka, N. Shibata, T. Takata, T. Hisatomi, K. Domen, Nature, 2021, 598, 304-307.
[4]	S. Ye, W. Shi, Y. Liu, D. Li, H. Yin, H. Chi, Y. Luo, N. Ta, F. Fan, X. Wang, J. Am. Chem. Soc., 2021, 143, 12499-12508.
[5]	M. Z. Rahman, M. G. Kibria, C. B. Mullins, Chem. Soc. Rev., 2020, 49, 1887-1931.
[6]	M. Rahman, H. Tian, T. Edvinsson, Angew. Chem. Int. Ed., 2020, 59, 16278-16293.
[7]	T. Banerjee, F. Podjaski, J. Kröger, B.-P. Biswal, B.-V. Lotsch, Nat. Rev. Mater., 2021, 6, 168-190.
[8]	J. F. Sui, H. Liu, S. J. Hu, K. Sun, G. Wan, H. Zhou, X. Zheng, H. L. Jiang, Adv. Mater., 2022, 34, 2109203.
[9]	Y. Yuan, Z. Yu, D. Chen, Z. Zou, Chem. Soc. Rev., 2017, 46, 603-631.
[10]	E. Nikoloudakis, I. López-Duarte, G. Charalambidis, K. Ladomenou, M. Ince, A. G. Coutsolelos, Chem. Soc. Rev., 2022, 51, 6965-7045.
[11]	C. Y. Zhang, H. Wang, H. B. Yu, K. X. Yi, W. Zhang, X. Z. Yuan, J. H. Huang, Y. C. Deng, G. M. Zeng, Adv. Energy Mater., 2022, 12, 2200875.
[12]	Y. Wang, A. Vogel, M. Sachs, R.-S. Sprick, L. Wilbraham, S.-J.-A. Moniz, R. Godin, M.-A. Zwijnenburg, J.-R. Durrant, A.-I. Cooper, J. Tang, Nat. Energy, 2019, 4, 746-760.
[13]	L. Yang, Y. T. Peng, X. D. Luo, Y. Dan, J. H. Ye, Y. Zhou, Z. G. Zou, Chem. Soc. Rev., 2021, 50, 2147-2172.
[14]	N. Zhang, Q. Yin, S. Guo, K. K. Chen, T. F. Liu, P. Wang, Z. M. Zhang, T. B. Lu, Appl. Catal. B, 2021, 296, 120337-120343.
[15]	S. Guo, L. H. Kong, P. Wang, S. Yao, T. B. Lu, Z. M. Zhang, Angew. Chem. Int. Ed., 2022, 61, e202206193.
[16]	C. X. Zhang, C. F. Xie, Y. Y. Gao, X. P Tao, C. M. Ding, F. T. Fan, H. L. Jiang, Angew. Chem. Int. Ed., 2022, 61, e202204108.
[17]	P. Y. Dong, A. C. Zhang, T. Cheng, J. K. Pan, J. Song, L. Zhang, R. F. Guan, X. G. Xi, J. L. Zhang, Chin. J. Catal., 2022, 43, 2592-2605.
[18]	M. Liu, Y. F. Mu, S. Yao, S. Guo, X. W. Guo, Z. M. Zhang, T. B. Lu, Appl. Catal. B, 2019, 245, 496-501.
[19]	A. Li, Q. Cao, G. Zhou, B.-V.-K.-J. Schmidt, W. J. Zhu, X. T. Yuan, H. L. Huo, J. L. Gong, M. Antonietti, Angew. Chem. Int. Ed., 2019, 58, 14549-14555.
[20]	L. Xie, S. Zhou, J. Liu, B. Qiu, T. Liu, Q. Liang, X. Zheng, B. Li, J. Zeng, M. Yan, J. Am. Chem. Soc., 2021, 143, 6922-6932.
[21]	J. Kosco, M. Bidwell, H. Cha, T. Martin, C.-T. Howells, M. Sachs, D.-H. Anjum, S. Gonzalez Lopez, L. Zou, A. Wadsworth, W. Zhang, L. Zhang, J. Tellam, R. Sougrat, F. Laquai, D.-M. DeLongchamp, J.-R. Durrant, I. McCulloch, Nat. Mater., 2020, 19, 559-565.
[22]	C.-S. Diercks, O.-M. Yaghi, Science, 2017, 355, 923.
[23]	R. Liu, K. T. Tan, Y. Gong, Y. Chen, Z. Li, S. Xie, T. He, Z. Lu, H. Yang, D. Jiang, Chem. Soc. Rev., 2021, 50, 120-242.
[24]	Q. Sun, B. Aguila, J.-A. Perman, T. Butts, F. Xiao, S. Ma, Chem, 2018, 4, 1726-1739.
[25]	X.-Y. Guan, H. Li, Y.-C. Ma, M. Xue, Q.-R. Fang, Y.-S. Yan, V. Valtchev, S.-L. Qiu, Nat. Chem., 2019, 11, 587-594.
[26]	H. Wang, H. Wang, Z. W. Wang, L. Tang, G. M. Zeng, P. Xu, M. Chen, T. Xiong, C. Y. Zhou, X. Y. Li, D. L. Huang, Y. Zhu, Z. X. Wang, J. W. Tang, Chem. Soc. Rev., 2020, 49, 4135-4165.
[27]	Q. H. Zhu, Z. H. Xu, B. C. Qiu, M. Y. Xing, J. L. Zhang, Small, 2021, 17, 2101070.
[28]	J. H. Yang, D. E. Wang, H. X. Han, C. Li, Acc. Chem. Res., 2013, 46, 1900-1909.
[29]	D. Wang, X. Q. Gong, Nat. Commun., 2021, 12, 158.
[30]	T. Banerjee, K. Gottschling, G. Savasci, C. Ochsenfeld, B.-V. Lotsch, ACS Energy Lett., 2018, 3, 400-409.
[31]	L. Stegbauer, K. Schwinghammer, B.-V. Lotsch, Chem. Sci., 2014, 5, 2789-2793.
[32]	V.-S. Vyas, F. Haase, L. Stegbauer, G. Savasci, F. Podjaski, C. Ochsenfeld, B.-V. Lotsch, Nat. Commun., 2015, 6, 8508.
[33]	K. W. Wang, Z. F. Jia, Y. Bai, X. Wang, S.-E. Hodgkiss, L. J. Chen, S. Y. Chong, X. Y. Wang, H. F. Yang, Y. J. Xu, F. Feng, J. W. Ward, A.-I. Cooper, J. Am. Chem. Soc., 2020, 142, 11131-11138.
[34]	X. Y. Wang, L. J. Chen, S. Y. Chong, M.-A. Little, Y. Z. Wu, W. H. Zhu, R. Clowes, Y. Yan, M.-A. Zwijnenburg, R.-S. Sprick, A.-I. Cooper, Nat. Chem., 2018, 10, 1180-1189.
[35]	J. Yang, A. Acharjya, M.-Y. Ye, J. Rabeah, S. Li, Z. Kochovski, S. Youk, J. Roeser, J. Grüneberg, C. Penschke, M. Schwarze, T. Wang, Y. Lu, R. Krol, M. Oschatz, R. Schomäcker, P. Saalfrank, A. Thomas, Angew. Chem. Int. Ed., 2021, 60, 19797-19803.
[36]	Y. L. Zhu, S. Wan, Y. H. Jin, W. Zhang, J. Am. Chem. Soc., 2015, 137, 13772-13775.
[37]	K. Y. Geng, T. He, R. Y. Liu, S. Dalapati, K. T. Tan, Z. P. Li, S. S. Tao, Y. F. Gong, Q. H. Jiang, D. L. Jiang, Chem. Rev., 2020, 120, 8814-8933.
[38]	A. Legrand, Z. Wang, J. Troyano, S. Furukawa, Chem. Sci., 2020, 12, 18-33.
[39]	W. B. Chen, P. Chen, D. Chen, Y. Liu, G. Zhang, L. Wang, L. Chen, Adv. Sci., 2022, 9, 2105517.
[40]	S. Mondal, B. Mohanty, M. Nurhuda, S. Dalapati, R. Jana, M. Addicoat, A. Datta, B. K. Jena, A. Bhaumik, ACS Catal., 2020, 10, 5623-5630.
[41]	D. H. Li, C. Y. Li, L. J. Zhang, H. Li, L. K. Zhu, D. J. Yang, Q. R. Fang, S. L. Qiu, X. D. Yao, J. Am. Chem. Soc., 2020, 142, 8104-8108.
[42]	S. L. Cai, K. Zhang, J. B. Tan, S. Wang, S. R. Zheng, J. Fan, Y. Yu, W. G. Zhang, Y. Liu, ACS Macro Lett., 2016, 5, 1348-1352.
[43]	S. Altarawneh, L. Nahar, I.-U. Arachchige, A.-O. El-Ballouli, K.-M. Hallal, B.-R. Kaafarani, M.-G. Rabbani, R.-K. Arvapally, H.-M. El-Kaderi, J. Mater. Chem. A, 2015, 3, 3006-3010.
[44]	A. Roy, S. Mondal, A. Halder, A. Banerjee, D. Ghoshal, A. Paul, S. Malik, Eur. Polym. J., 2017, 93, 448-457.
[45]	B.-C. Patra, S. Khilari, L. Satyanarayana, D. Pradhan, A. Bhaumik, Chem. Commun., 2016, 52, 7592-7595.
[46]	A. Wang, J. Li, T. Zhang, Nat. Rev. Chem., 2018, 2, 65-81.
[47]	C. Gao, J. X. Low, R. Long, T. T. Kong, J. F. Zhu, Y. J. Xiong, Chem. Rev., 2020, 120, 12175-12216.
[48]	M. Lu, M. Zhang, C. G. Liu, J. Liu, L. J. Shang, M. Wang, J. N. Chang, S. L. Li, Y. Q. Lan, Angew. Chem. Int. Ed., 2021, 60, 4864-4871.
[49]	R.-R. Liang, S.-Y. Jiang, R.-H. A, X. Zhao, Chem. Soc. Rev., 2020, 49, 3920-3951.
[50]	J. T. Ming, A. Liu, J. W. Zhao, P. Zhang, H. W. Huang, H. Lin, Z. T. Xu, X. M. Zhang, X. X. Wang, J. Hofkens, M.-B.-J. Roeffaers, J. L. Long, Angew. Chem. Int. Ed., 2019, 58, 18290-18294.
[51]	S. Kandambeth, A. Mallick, B. Lukose, M.-V. Mane, T. Heine, R. Banerjee, J. Am. Chem. Soc., 2012, 134, 19524-19527.
[52]	S. Nandi, S.-K. Singh, D. Mullangi, R. Illathvalappil, L. George, C.-P. Vinod, S. Kurungot, R. Vaidhyanathan, Adv. Energy Mater., 2016, 6, 1601189.
[53]	S. L. Wang, M. Xu, T. Y. Peng, C. X. Zhang, T. Li, I. Hussain, J. Y. Wang, B. E. Tan, Nat. Commun., 2019, 10, 676.
[54]	H. X. Zhong, M. C. Wang, M. Ghorbani-Asl, J. C. Zhang, K. H. Ly, Z. Q. Liao, G. B. Chen, Y. D. Wei, B.-P. Biswal, E. Zschech, I.-M. Weidinger, A.-V. Krasheninnikov, R. H. Dong, X. L. Feng, J. Am. Chem. Soc., 2021, 143, 19992-20000.
[55]	C. Y. Li, G. Yu, Small, 2021, 17, 2100918.
[56]	K. Y. Geng, T. He, R. Y. Liu, S. Dalapati, K. T. Tan, Z. P. Li, S. S. Tao, Y. F. Gong, Q. H. Jiang, D. L. Jiang, Chem. Rev., 2020, 120, 8814-8933.
[57]	Z. Xie, B. Wang, Z. F. Yang, X. Yang, X. Yu, G. L. Xing, Y. H. Zhang, L. Chen, Angew. Chem. Int. Ed., 2019, 58, 15742-15746.
[58]	J. J. Cao, W. J. Shan, Q. Wang, X. C. Ling, G. Q. Li, Y. N. Lyu, Y. Zhou, J. Wang, ACS Appl. Mater. Interfaces, 2019, 11, 6031-6041.
[59]	C. Chen, Y. Xiong, X. Zhong, P. C. Lan, Z. Wei, H. Pan, P. Su, Y. Song, Y. Chen, A. Nafady, Angew. Chem. Int. Ed., 2022, 61, 202114071.
[60]	A. Hankin, F.-E. Bedoya-Lora, J.-C. Alexander, A. Regoutz, G.-H. Kelsall, J. Mater. Chem. A, 2019, 7, 26162-26176.
[61]	R. F. Chen, Y. Wang, Y. Ma, A. Mal, X. Y. Gao, L. Gao, L. J. Qiao, X. B. Li, L. Z. Wu, C. Wang, Nat. Commun., 2021, 12, 1354.
[62]	P. Y. Dong, Y. Wang, A. C. J. Zhang, T. Cheng, X. G. Xi, J. L. Zhang, ACS Catal., 2021, 11, 13266-13279.
[63]	S. Bi, C. Yang, W. B. Zhang, J. S. Xu, L. M. Liu, D. Q. Wu, X. C. Wang, Y. Han, Q. F. Liang, F. Zhang, Nat. Commun., 2019, 10, 2467.
[64]	S. Gao, B. C. Gu, X. C. Jiao, Y. F. Sun, X. L. Zu, F. Yang, W. G. Zhu, C. M. Wang, Z. M. Feng, B. J. Ye, Y. Xie, J. Am. Chem. Soc., 2017, 139, 3438-3445.
[65]	K. L. Zhou, Z. L. Wang, C. B. Han, X. Ke, C. H. Wang, Y. H. Jin, Q. Q. Zhang, J. B. Liu, H. Wang, H. Yan, Nat. Commun., 2021, 12, 3783.
[66]	Y. Joly, Phys. Rev. B., 2001, 63, 125120.
[67]	M.-J. Hülsey, B. Zhang, Z. Ma, H. Asakura, D.-A. Do, W. Chen, T. Tanaka, P. Zhang, Z. Wu, N. Yan, Nat. Commun., 2019, 10, 1330.
[68]	M.-Z. Alam, I. De Leon, R.-W. Boyd, Science, 2016, 352, 795-797.
[69]	L. Y. Zeng, Z. L. Zhao, F. Lv, Z. H. Xia, S. Y. Lu, J. Li, K. A. Sun, K. Wang, Y. J. Sun, Q. Z. Huang, Y. Chen, Q. H. Zhang, L. Gu, G. Lu, S. J. Guo, Nat. Commun., 2022, 13, 3822.
[70]	H. C. Hu, W. H. Guan, Y. F. Xu, X. C. Wang, L. Z. Wu, M. Chen, Q. X. Zhong, Y. Xu, Y. Y. Li, T. Sham, X. H. Zhang, L. Wang, M. Cao, Q. Zhang, ACS Nano, 2021, 15, 13129-13139.
[71]	L. Su, P. Wang, J. Wang, D. Zhang, H. Wang, Y. Li, Zhan, S. J. Gong, Adv. Funct. Mater., 2021, 31, 2104343.
[72]	H. M. Zhang, W. H. Liu, D. C. Cao, D. J. Cheng, iScience, 2022, 25, 104367.
[73]	Q. Fu, Z. Y. Xu, X. C. Tang, T. T. Liu, X. Y. Dong, X. D. Zhang, N. Zheng, Z. Q. Xie, Y. S. Liu, ACS Energy Lett., 2021, 6, 1521-1532.
[74]	L. P. Liu, H. B. Meng, Y. Q. Chai, X. J. Chen, J. Y. Xu, X. L. Liu, W. X. Liu, D.-M. Guldi, Y. F. Zhu, Angew. Chem. Int. Ed., 2023, 62, e202217897.
[75]	J. Yang, J. F. Jing, Y. F. Zhu, Adv. Mater., 2021, 33, 2101026.
[76]	W. Q. Li, X. F. Huang, T. W. Zeng, Y. A. Liu, W. B. Hu, H. Yang, Y. B. Zhang, K. Wen, Angew. Chem. Int. Ed., 2021, 60, 1869-1874.
[77]	X. W. Ruan, C. X. Huang, H. Cheng, Z. Q. Zhang, Y. Cui, Z. Y. Li, T. F. Xie, K. K. Ba, H. Y. Zhang, L. Zhang, X. Zhao, J. Leng, S. Y. Jin, W. Zhang, W. T. Zheng, S. K. Ravi, Z. F. Jiang, X. Q. Cui, J. G. Yu, Adv. Mater., 2023, 35, 2209141.
[78]	H. X. Lin, Y. Liu, Z. R. Wang, L. Y. Ling, H. Huang, Q. H. Li, L. X. Cheng, Y. B. Li, J. L. Zhou, K. F. Wu, J. Zhang, T. H. Zhou, Angew. Chem. Int. Ed., 2022, 61, e202214142.
[79]	F. Haase, T. Banerjee, G. Savasci, C. Ochsenfeld, B.-V. Lotsch, Faraday Discuss., 2017, 201, 247-264.
[80]	A.-V. Marenich, C.-J. Cramer, D.-G. Truhlar, J. Phys. Chem. B, 2009, 113, 6378-6396.
[81]	F.-M. Zhang, J.-L. Sheng, Z.-D. Yang, X.-J. Sun, H.-L. Tang, M. Lu, H. Dong, F.-C. Shen, J. Liu, Y.-Q. Lan, Angew. Chem. Int. Ed., 2018, 57, 12106-12110.
[82]	Z. F. Zhao, Y. L. Zheng, C. Wang, S. N. Zhang, J. Song, Y. F. Li, S. Q. Ma, P. Cheng, Z. J. Zhang, Y. Chen, ACS Catal., 2021, 11, 2098-2107.