Zr-Based Metal−Organic Frameworks with Phosphoric Acids for the Photo-Oxidation of Sulfides
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis and Characterization
2.2. Photo-Oxidation of Thioanisol
2.3. Photocatalytic Mechanism
2.4. Substrate Compatibility and Recyclability
3. Materials and Methods
3.1. Instruments
3.2. Synthesis
3.3. Electrochemical Characterization
3.4. Photocatalytic Reaction
3.5. EPR Measurements
3.6. ROS Detection with Probe Molecules
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
- Wang, S.S.; Yang, G.Y. Recent Advances in Polyoxometalate-Catalyzed Reactions. Chem. Rev. 2015, 115, 4893–4962. [Google Scholar] [CrossRef] [PubMed]
- Mansir, N.; Taufiq-Yap, Y.H.; Rashid, U.; Lokman, I.M. Investigation of heterogeneous solid acid catalyst performance on low grade feedstocks for biodiesel production: A review. Energy Convers. Manag. 2017, 141, 171–182. [Google Scholar] [CrossRef]
- Doustkhah, E.; Lin, J.; Rostamnia, S.; Len, C.; Luque, R.; Luo, X.; Bando, Y.; Wu, K.C.; Kim, J.; Yamauchi, Y.; et al. Development of Sulfonic-Acid-Functionalized Mesoporous Materials: Synthesis and Catalytic Applications. Chem. Eur. J. 2019, 25, 1614–1635. [Google Scholar] [CrossRef] [PubMed]
- Buru, C.T.; Farha, O.K. Strategies for Incorporating Catalytically Active Polyoxometalates in Metal−Organic Frameworks for Organic Transformations. ACS Appl. Mater. Interfaces 2020, 12, 5345–5360. [Google Scholar] [CrossRef]
- Gong, W.; Liu, Y.; Li, H.; Cui, Y. Metal-organic frameworks as solid Brønsted acid catalysts for advanced organic transformations. Coord. Chem. Rev. 2020, 420, 213400. [Google Scholar] [CrossRef]
- Chen, Y.; Guerin, S.; Yuan, H.; O’Donnell, J.; Xue, B.; Cazade, P.A.; Haq, E.U.; Shimon, L.J.W.; Rencus-Lazar, S.; Tofail, S.A.M.; et al. Guest Molecule-Mediated Energy Harvesting in a Conformationally Sensitive Peptide-Metal Organic Framework. J. Am. Chem. Soc. 2022, 144, 3468–3476. [Google Scholar] [CrossRef]
- Zheng, M.; Liu, Y.; Wang, C.; Liu, S.; Lin, W. Cavity-induced enantioselectivity reversal in a chiral metal–organic framework Brønsted acid catalyst. Chem. Sci. 2012, 3, 2623–2627. [Google Scholar] [CrossRef]
- Zhang, Z.; Ji, Y.R.; Wojtas, L.; Gao, W.Y.; Ma, S.; Zaworotko, M.J.; Antilla, J.C. Two homochiral organocatalytic metal organic materials with nanoscopic channels. Chem. Commun. 2013, 49, 7693–7695. [Google Scholar] [CrossRef]
- Chen, X.; Jiang, H.; Li, X.; Hou, B.; Gong, W.; Wu, X.; Han, X.; Zheng, F.; Liu, Y.; Jiang, J.; et al. Chiral Phosphoric Acids in Metal–Organic Frameworks with Enhanced Acidity and Tunable Catalytic Selectivity. Angew. Chem. Int. Ed. 2019, 58, 14748–14757. [Google Scholar] [CrossRef]
- Gong, W.; Chen, X.; Jiang, H.; Chu, D.; Cui, Y.; Liu, Y. Highly Stable Zr(IV)-Based Metal–Organic Frameworks with Chiral Phosphoric Acids for Catalytic Asymmetric Tandem Reactions. J. Am. Chem. Soc. 2019, 141, 7498–7508. [Google Scholar] [CrossRef] [PubMed]
- Dorneles de Mello, M.; Kumar, G.; Tabassum, T.; Jain, S.K.; Chen, T.H.; Caratzoulas, S.; Li, X.; Vlachos, D.G.; Han, S.I.; Scott, S.L.; et al. Phosphonate-Modified UiO-66 Brønsted Acid Catalyst and Its Use in Dehydra-Decyclization of 2-Methyltetrahydrofuran to Pentadienes. Angew. Chem. Int. Ed. 2020, 59, 13260–13266. [Google Scholar] [CrossRef] [PubMed]
- Fang, X.; Shang, Q.; Wang, Y.; Jiao, L.; Yao, T.; Li, Y.; Zhang, Q.; Luo, Y.; Jiang, H.L. Single Pt Atoms Confined into a Metal–Organic Framework for Efficient Photocatalysis. Adv. Mater. 2018, 30, 1705112. [Google Scholar] [CrossRef] [PubMed]
- Wu, X.P.; Gagliardi, L.; Truhlar, D.G. Cerium Metal–Organic Framework for Photocatalysis. J. Am. Chem. Soc. 2018, 140, 7904–7912. [Google Scholar] [CrossRef] [PubMed]
- Xiao, Y.; Qi, Y.; Wang, X.; Wang, X.; Zhang, F.; Li, C. Visible-Light-Responsive 2D Cadmium–Organic Framework Single Crystals with Dual Functions of Water Reduction and Oxidation. Adv. Mater. 2018, 30, 1803401. [Google Scholar] [CrossRef] [PubMed]
- Zuo, Q.; Liu, T.; Chen, C.; Ji, Y.; Gong, X.; Mai, Y.; Zhou, Y. Ultrathin Metal-Organic Framework Nanosheets with Ultrahigh Loading of Single Pt Atoms for Efficient Visible-Light-Driven Photocatalytic H2 Evolution. Angew. Chem. Int. Ed. Engl. 2019, 58, 10198–10203. [Google Scholar] [CrossRef]
- Xiao, J.D.; Han, L.; Luo, J.; Yu, S.H.; Jiang, H.L. Integration of Plasmonic Effects and Schottky Junctions into Metal-Organic Framework Composites: Steering Charge Flow for Enhanced Visible-Light Photocatalysis. Angew. Chem. Int. Ed. 2018, 57, 1103–1107. [Google Scholar] [CrossRef]
- Qin, J.S.; Yuan, S.; Zhang, L.; Li, B.; Du, D.Y.; Huang, N.; Guan, W.; Drake, H.F.; Pang, J.; Lan, Y.Q.; et al. Creating Well-Defined Hexabenzocoronene in Zirconium Metal–Organic Framework by Postsynthetic Annulation. J. Am. Chem. Soc. 2019, 141, 2054–2060. [Google Scholar] [CrossRef]
- Wang, X.-K.; Liu, J.; Zhang, L.; Dong, L.-Z.; Li, S.-L.; Kan, Y.-H.; Li, D.-S.; Lan, Y.-Q. Monometallic Catalytic Models Hosted in Stable Metal-Organic Frameworks for Tunable CO2 Photoreduction. ACS Catal. 2019, 9, 1726–1732. [Google Scholar] [CrossRef]
- Kong, X.J.; He, T.; Zhou, J.; Zhao, C.; Li, T.C.; Wu, X.Q.; Wang, K.; Li, J.R. In Situ Porphyrin Substitution in a Zr(IV)-MOF for Stability Enhancement and Photocatalytic CO2 Reduction. Small 2021, 17, 2005357. [Google Scholar] [CrossRef]
- Gao, Y.; Li, S.; Li, Y.; Yao, L.; Zhang, H. Accelerated photocatalytic degradation of organic pollutant over metal-organic framework MIL-53(Fe) under visible LED light mediated by persulfate. Appl. Catal. B 2017, 202, 165–174. [Google Scholar] [CrossRef]
- Li, M.; Zheng, Z.; Zheng, Y.; Cui, C.; Li, C.; Li, Z. Controlled Growth of Metal-Organic Framework on Upconversion Nanocrystals for NIR-Enhanced Photocatalysis. ACS Appl. Mater. Interfaces 2017, 9, 2899–2905. [Google Scholar] [CrossRef] [PubMed]
- Buru, C.T.; Majewski, M.B.; Howarth, A.J.; Lavroff, R.H.; Kung, C.W.; Peters, A.W.; Goswami, S.; Farha, O.K. Improving the Efficiency of Mustard Gas Simulant Detoxification by Tuning the Singlet Oxygen Quantum Yield in Metal–Organic Frameworks and Their Corresponding Thin Films. ACS Appl. Mater. Interfaces 2018, 10, 23802–23806. [Google Scholar] [CrossRef] [PubMed]
- Gómez-Avilés, A.; Peñas-Garzón, M.; Bedia, J.; Dionysiou, D.D.; Rodríguez, J.J.; Belver, C. Mixed Ti-Zr metal-organic-frameworks for the photodegradation of acetaminophen under solar irradiation. Appl. Catal. B 2019, 253, 253–262. [Google Scholar] [CrossRef]
- Yuan, S.; Liu, T.F.; Feng, D.; Tian, J.; Wang, K.; Qin, J.; Zhang, Q.; Chen, Y.P.; Bosch, M.; Zou, L.; et al. A single crystalline porphyrinic titanium metal-organic framework. Chem. Sci. 2015, 6, 3926–3930. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Nguyen, H.L.; Vu, T.T.; Le, D.; Doan, T.L.H.; Nguyen, V.Q.; Phan, N.T.S. A Titanium–Organic Framework: Engineering of the Band-Gap Energy for Photocatalytic Property Enhancement. ACS Catal. 2016, 7, 338–342. [Google Scholar] [CrossRef]
- Zeng, L.; Guo, X.; He, C.; Duan, C. Metal–Organic Frameworks: Versatile Materials for Heterogeneous Photocatalysis. ACS Catal. 2016, 6, 7935–7947. [Google Scholar] [CrossRef]
- Zhu, Y.Y.; Lan, G.; Fan, Y.; Veroneau, S.S.; Song, Y.; Micheroni, D.; Lin, W. Merging Photoredox and Organometallic Catalysts in a Metal–Organic Framework Significantly Boosts Photocatalytic Activities. Angew. Chem. Int. Ed. 2018, 57, 14090–14094. [Google Scholar] [CrossRef]
- Chen, Y.; Yang, Y.; Orr, A.A.; Makam, P.; Redko, B.; Haimov, E.; Wang, Y.; Shimon, L.J.W.; Rencus-Lazar, S.; Ju, M.; et al. Self-Assembled Peptide Nano-Superstructure towards Enzyme Mimicking Hydrolysis. Angew. Chem. Int. Ed. 2021, 60, 17164–17170. [Google Scholar] [CrossRef]
- Maji, R.; Mallojjala, S.C.; Wheeler, S.E. Chiral phosphoric acid catalysis: From numbers to insights. Chem. Soc. Rev. 2018, 47, 1142–1158. [Google Scholar] [CrossRef]
- Xia, Z.L.; Xu-Xu, Q.F.; Zheng, C.; You, S.L. Chiral phosphoric acid-catalyzed asymmetric dearomatization reactions. Chem. Soc. Rev. 2020, 49, 286–300. [Google Scholar] [CrossRef]
- Padalkar, V.S.; Seki, S. Excited-state intramolecular proton-transfer (ESIPT)-inspired solid state emitters. Chem. Soc. Rev. 2016, 45, 169–202. [Google Scholar] [CrossRef] [PubMed]
- Wang, W.; Marshall, M.; Collins, E.; Marquez, S.; Mu, C.; Bowen, K.H.; Zhang, X. Intramolecular electron-induced proton transfer and its correlation with excited-state intramolecular proton transfer. Nat. Commun. 2019, 10, 1170. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Man, Z.; Lv, Z.; Xu, Z.; Liu, M.; He, J.; Liao, Q.; Yao, J.; Peng, Q.; Fu, H. Excitation-Wavelength-Dependent Organic Long-Persistent Luminescence Originating from Excited-State Long-Range Proton Transfer. J. Am. Chem. Soc. 2022, 144, 12652–12660. [Google Scholar] [CrossRef] [PubMed]
- Rueping, M.; Kuenkel, A.; Atodiresei, I. Chiral Bronsted acids in enantioselective carbonyl activations—Activation modes and applications. Chem. Soc. Rev. 2011, 40, 4539–4549. [Google Scholar] [CrossRef] [PubMed]
- Velmurugan, K.; Nandhakumar, R. Binol based “turn on” fluorescent chemosensor for mercury ion. J. Lumin. 2015, 162, 8–13. [Google Scholar] [CrossRef]
- Reid, J.P.; Simon, L.; Goodman, J.M. A Practical Guide for Predicting the Stereochemistry of Bifunctional Phosphoric Acid Catalyzed Reactions of Imines. Acc. Chem. Res. 2016, 49, 1029–1041. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Zhang, Z.; Wang, Y.; Nakano, T. Photo Racemization and Polymerization of (R)-1,1′-Bi(2-naphthol). Molecules 2016, 21, 1541. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Posey, V.; Hanson, K. Chirality and Excited State Proton Transfer: From Sensing to Asymmetric Synthesis. ChemPhotoChem 2019, 3, 580–604. [Google Scholar] [CrossRef]
- Kaji, D.; Kitayama, M.; Hara, N.; Yoshida, K.; Wakabayashi, S.; Shizuma, M.; Tsubaki, K.; Imai, Y. Sign control of circularly polarized luminescence by substituent domino effect in binaphthyl-Eu(III) organometallic luminophores. J. Photoch. Photobio. A 2020, 397, 112490. [Google Scholar] [CrossRef]
- Pulis, A.P.; Procter, D.J. C–H Coupling Reactions Directed by Sulfoxides: Teaching an Old Functional Group New Tricks. Angew. Chem. Int. Ed. 2016, 55, 9842–9860. [Google Scholar] [CrossRef]
- Han, J.; Soloshonok, V.A.; Klika, K.D.; Drabowicz, J.; Wzorek, A. Chiral sulfoxides: Advances in asymmetric synthesis and problems with the accurate determination of the stereochemical outcome. Chem. Soc. Rev. 2018, 47, 1307–1350. [Google Scholar] [CrossRef] [PubMed]
- Wojaczyńska, E.; Wojaczyński, J. Modern Stereoselective Synthesis of Chiral Sulfinyl Compounds. Chem. Rev. 2020, 120, 4578–4611. [Google Scholar] [CrossRef] [PubMed]
- Liang, X.; Guo, Z.; Wei, H.; Liu, X.; Lv, H.; Xing, H. Selective photooxidation of sulfides mediated by singlet oxygen using visible-light-responsive coordination polymers. Chem. Commun. 2018, 54, 13002–13005. [Google Scholar] [CrossRef]
- Wei, L.Q.; Ye, B.H. Cyclometalated Ir–Zr Metal–Organic Frameworks as Recyclable Visible-Light Photocatalysts for Sulfide Oxidation into Sulfoxide in Water. ACS Appl. Mater. Interfaces 2019, 11, 41448–41457. [Google Scholar] [CrossRef] [PubMed]
- Meng, Y.; Luo, Y.; Shi, J.L.; Ding, H.; Lang, X.; Chen, W.; Zheng, A.; Sun, J.; Wang, C. 2D and 3D Porphyrinic Covalent Organic Frameworks: The Influence of Dimensionality on Functionality. Angew. Chem. Int. Ed. 2020, 59, 3624–3629. [Google Scholar] [CrossRef] [PubMed]
- Hao, Y.; Papazyan, E.K.; Ba, Y.; Liu, Y. Mechanism-Guided Design of Metal–Organic Framework Composites for Selective Photooxidation of a Mustard Gas Simulant under Solvent-Free Conditions. ACS Catal. 2021, 12, 363–371. [Google Scholar] [CrossRef]
- Liu, M.; Liu, J.; Zhou, K.; Chen, J.; Sun, Q.; Bao, Z.; Yang, Q.; Yang, Y.; Ren, Q.; Zhang, Z. Turn-On Photocatalysis: Creating Lone-Pair Donor-Acceptor Bonds in Organic Photosensitizer to Enhance Intersystem Crossing. Adv. Sci. 2021, 8, 2100631. [Google Scholar] [CrossRef]
- Sadeghfar, F.; Zalipour, Z.; Taghizadeh, M.; Taghizadeh, A.; Ghaedi, M. Photodegradation Processes. In Interface Science and Technology; Ghaedi, M., Ed.; Elsevier: Amsterdam, The Netherlands, 2021; Volume 32, pp. 55–124. [Google Scholar]
- Li, Y.; Rizvi, S.A.; Hu, D.; Sun, D.; Gao, A.; Zhou, Y.; Li, J.; Jiang, X. Selective Late-Stage Oxygenation of Sulfides with Ground-State Oxygen by Uranyl Photocatalysis. Angew. Chem. Int. Ed. 2019, 58, 13499–13506. [Google Scholar] [CrossRef]
- Furukawa, H.; Gándara, F.; Zhang, Y.B.; Jiang, J.; Queen, W.L.; Hudson, M.R.; Yaghi, O.M. Water Adsorption in Porous Metal–Organic Frameworks and Related Materials. J. Am. Chem. Soc. 2014, 136, 4369–4381. [Google Scholar] [CrossRef]
- Zhang, M.; Chen, Y.P.; Bosch, M.; Gentle, T., III; Wang, K.; Feng, D.; Wang, Z.U.; Zhou, H.C. Symmetry-Guided Synthesis of Highly Porous Metal–Organic Frameworks with Fluorite Topology. Angew. Chem. Int. Ed. 2014, 53, 815–818. [Google Scholar] [CrossRef]
- Wang, S.; Wang, J.; Cheng, W.; Yang, X.; Zhang, Z.; Xu, Y.; Liu, H.; Wu, Y.; Fang, M. A Zr metal–organic framework based on tetrakis(4-carboxyphenyl) silane and factors affecting the hydrothermal stability of Zr-MOFs. Dalton Trans. 2015, 44, 8049–8061. [Google Scholar] [CrossRef] [PubMed]
- Ma, J.; Tran, L.D.; Matzger, A.J. Toward Topology Prediction in Zr-Based Microporous Coordination Polymers: The Role of Linker Geometry and Flexibility. Cryst. Growth Des. 2016, 16, 4148–4153. [Google Scholar] [CrossRef]
- Spek, A.L. Single-crystal structure validation with the program PLATON. J. Appl. Crystallogr. 2003, 36, 7–13. [Google Scholar] [CrossRef] [Green Version]
- Zhang, J.; Chen, X.; Takanabe, K.; Maeda, K.; Domen, K.; Epping, J.D.; Fu, X.; Antonietti, M.; Wang, X. Synthesis of a Carbon Nitride Structure for Visible-Light Catalysis by Copolymerization. Angew. Chem. Int. Ed. 2010, 49, 441–444. [Google Scholar] [CrossRef]
- Wang, J.; Yu, Y.; Zhang, L. Highly efficient photocatalytic removal of sodium pentachlorophenate with Bi3O4Br under visible light. Appl. Catal. B 2013, 136–137, 112–121. [Google Scholar] [CrossRef]
- Xu, H.Q.; Hu, J.; Wang, D.; Li, Z.; Zhang, Q.; Luo, Y.; Yu, S.H.; Jiang, H.L. Visible-Light Photoreduction of CO2 in a Metal–Organic Framework: Boosting Electron–Hole Separation via Electron Trap States. J. Am. Chem. Soc. 2015, 137, 13440–13443. [Google Scholar] [CrossRef]
- Colomer, I.; Chamberlain, A.E.R.; Haughey, M.B.; Donohoe, T.J. Hexafluoroisopropanol as a highly versatile solvent. Nat. Rev. Chem. 2017, 1, 1–12. [Google Scholar] [CrossRef]
- Pistritto, V.A.; Schutzbach-Horton, M.E.; Nicewicz, D.A. Nucleophilic Aromatic Substitution of Unactivated Fluoroarenes Enabled by Organic Photoredox Catalysis. J. Am. Chem. Soc. 2020, 142, 17187–17194. [Google Scholar] [CrossRef]
- Dellinger, B.; Lomnicki, S.; Khachatryan, L.; Maskos, Z.; Hall, R.W.; Adounkpe, J.; McFerrin, C.; Truong, H. Formation and stabilization of persistent free radicals. Proc. Combust. Inst. 2007, 31, 521–528. [Google Scholar] [CrossRef]
Entry | Solvent | Change in Other Conditions | Yield 2/% |
---|---|---|---|
1 | MeCN | none | 19 |
2 | MeOH | none | 58 |
3 | EtOH | none | 74 |
4 | EtOAc | none | trace |
5 | CF3CH2OH | none | 97 (95) 3 |
6 | CHCl3 | none | 56 |
7 | DMF | none | 3 |
8 | CF3CH2OH | no photocatalyst | 1 |
9 | CF3CH2OH | dark | n.d. 4 |
10 | CF3CH2OH | N2 atmosphere | n.d. 4 |
Entry | Photocatalyst | Additive | Yield 2/% |
---|---|---|---|
1 | Zr-MOF-P | none | 97 |
2 | Zr-MOF-P | DABCO | 95 |
3 | Zr-MOF-P | BQ | 96 |
4 | Zr-MOF-P | i-PrOH | 94 |
5 | Zr-MOF-P | catalase 3 | 93 |
6 | Zr-MOF-P | HQ | 10 |
7 | Zr-MOF-P | CuSO4 | 18 |
8 | Zr-MOF-P | DMB | 78 |
9 4 | L1Me4 | none | 99 |
10 4 | L1Me4 | DABCO | 91 |
11 4 | L1Me4 | BQ | 98 |
12 4 | L1Me4 | i-PrOH | 92 |
13 4 | L1Me4 | HQ | 11 |
14 4 | L1Me4 | CuSO4 | 26 |
15 4 | L1Me4 | DMB | 15 |
16 4 | L2Me4 | none | 2 |
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Zhao, Z.; Liu, M.; Zhou, K.; Gong, H.; Shen, Y.; Bao, Z.; Yang, Q.; Ren, Q.; Zhang, Z. Zr-Based Metal−Organic Frameworks with Phosphoric Acids for the Photo-Oxidation of Sulfides. Int. J. Mol. Sci. 2022, 23, 16121. https://doi.org/10.3390/ijms232416121
Zhao Z, Liu M, Zhou K, Gong H, Shen Y, Bao Z, Yang Q, Ren Q, Zhang Z. Zr-Based Metal−Organic Frameworks with Phosphoric Acids for the Photo-Oxidation of Sulfides. International Journal of Molecular Sciences. 2022; 23(24):16121. https://doi.org/10.3390/ijms232416121
Chicago/Turabian StyleZhao, Zhenghua, Mingjie Liu, Kai Zhou, Hantao Gong, Yajing Shen, Zongbi Bao, Qiwei Yang, Qilong Ren, and Zhiguo Zhang. 2022. "Zr-Based Metal−Organic Frameworks with Phosphoric Acids for the Photo-Oxidation of Sulfides" International Journal of Molecular Sciences 23, no. 24: 16121. https://doi.org/10.3390/ijms232416121