An Artificial Light-harvesting System Constructed from a Water-soluble Metal-organic Barrel for Photocatalytic Aerobic Reactions in Aqueous Media

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2023 Sep 22

PMID 37736644

Authors

Danyang Li

Linlin Yang

Wangjian Fang

Xinmei Fu

Hechuan Li

Jianxu Li

Xuezhao Li

Cheng He

Affiliations

Soon will be listed here.

Abstract

An artificial light-harvesting system constructed from a water-soluble host-guest complex can be regarded as a high-level conceptual model of its biological counterpart and can convert solar energy into chemical energy in an aqueous environment. Herein, a water-soluble metal-organic barrel Ga-tpe with twelve sulfonic acid units was obtained by subcomponent self-assembly between Ga ions and tetra-topic ligands with tetraphenylethylene (TPE) cores. By taking advantage of host-guest interactions, cationic dye rhodamine B (RB) was constrained in the pocket of Ga-tpe to promote the Förster resonance energy transfer (FRET) process for efficient photocatalytic aerobic oxidation of sulfides and cross-dehydrogenative coupling (CDC) reaction in aqueous media.

References

Oshovsky G, Reinhoudt D, Verboom W . Supramolecular chemistry in water. Angew Chem Int Ed Engl. 2007; 46(14):2366-93. DOI: 10.1002/anie.200602815. View

Li Y, Dong Y, Cheng L, Qin C, Nian H, Zhang H . Aggregation-Induced Emission and Light-Harvesting Function of Tetraphenylethene-Based Tetracationic Dicyclophane. J Am Chem Soc. 2019; 141(21):8412-8415. DOI: 10.1021/jacs.9b02617. View

Zhang D, Yu W, Li S, Xia Y, Li X, Li Y . Artificial Light-Harvesting Metallacycle System with Sequential Energy Transfer for Photochemical Catalysis. J Am Chem Soc. 2021; 143(3):1313-1317. DOI: 10.1021/jacs.0c12522. View

Gou X, Liu T, Wang Y, Han Y . Ultrastable and Highly Catalytically Active N-Heterocyclic-Carbene-Stabilized Gold Nanoparticles in Confined Spaces. Angew Chem Int Ed Engl. 2020; 59(38):16683-16689. DOI: 10.1002/anie.202006569. View

Xu L, Wang Z, Wang R, Wang L, He X, Jiang H . A Conjugated Polymeric Supramolecular Network with Aggregation-Induced Emission Enhancement: An Efficient Light-Harvesting System with an Ultrahigh Antenna Effect. Angew Chem Int Ed Engl. 2019; 59(25):9908-9913. DOI: 10.1002/anie.201907678. View

Cullen W, Misuraca M, Hunter C, Williams N, Ward M . Highly efficient catalysis of the Kemp elimination in the cavity of a cubic coordination cage. Nat Chem. 2016; 8(3):231-6. DOI: 10.1038/nchem.2452. View

Percastegui E, Mosquera J, Ronson T, Plajer A, Kieffer M, Nitschke J . Waterproof architectures through subcomponent self-assembly. Chem Sci. 2019; 10(7):2006-2018. PMC: 6385555. DOI: 10.1039/c8sc05085f. View

Forchetta M, Sabuzi F, Stella L, Conte V, Galloni P . KuQuinone as a Highly Stable and Reusable Organic Photocatalyst in Selective Oxidation of Thioethers to Sulfoxides. J Org Chem. 2022; 87(21):14016-14025. DOI: 10.1021/acs.joc.2c01648. View

Cook T, Zheng Y, Stang P . Metal-organic frameworks and self-assembled supramolecular coordination complexes: comparing and contrasting the design, synthesis, and functionality of metal-organic materials. Chem Rev. 2012; 113(1):734-77. PMC: 3764682. DOI: 10.1021/cr3002824. View

10.

Jing Y, Li S, Su M, Bao H, Wan W . Barbier Hyperbranching Polymerization-Induced Emission toward Facile Fabrication of White Light-Emitting Diode and Light-Harvesting Film. J Am Chem Soc. 2019; 141(42):16839-16848. DOI: 10.1021/jacs.9b08065. View

11.

Takezawa H, Shitozawa K, Fujita M . Enhanced reactivity of twisted amides inside a molecular cage. Nat Chem. 2020; 12(6):574-578. DOI: 10.1038/s41557-020-0455-y. View

12.

Cook T, Stang P . Recent Developments in the Preparation and Chemistry of Metallacycles and Metallacages via Coordination. Chem Rev. 2015; 115(15):7001-45. DOI: 10.1021/cr5005666. View

13.

Howlader P, Mondal B, Purba P, Zangrando E, Mukherjee P . Self-Assembled Pd(II) Barrels as Containers for Transient Merocyanine Form and Reverse Thermochromism of Spiropyran. J Am Chem Soc. 2018; 140(25):7952-7960. DOI: 10.1021/jacs.8b03946. View

14.

Cullen W, Takezawa H, Fujita M . Demethylenation of Cyclopropanes via Photoinduced Guest-to-Host Electron Transfer in an M L Cage. Angew Chem Int Ed Engl. 2019; 58(27):9171-9173. DOI: 10.1002/anie.201904752. View

15.

Hou Y, Zhang Z, Lu S, Yuan J, Zhu Q, Chen W . Highly Emissive Perylene Diimide-Based Metallacages and Their Host-Guest Chemistry for Information Encryption. J Am Chem Soc. 2020; 142(44):18763-18768. DOI: 10.1021/jacs.0c09904. View

16.

Kumar A, Saha R, Mukherjee P . Self-assembled metallasupramolecular cages towards light harvesting systems for oxidative cyclization. Chem Sci. 2021; 12(14):5319-5329. PMC: 8179592. DOI: 10.1039/d1sc00097g. View

17.

Lian Z, He J, Liu L, Fan Y, Chen X, Jiang H . [2,2] Paracyclophanes-based double helicates for constructing artificial light-harvesting systems and white LED device. Nat Commun. 2023; 14(1):2752. PMC: 10182020. DOI: 10.1038/s41467-023-38405-9. View

18.

Taylor L, Riddell I, Smulders M . Self-Assembly of Functional Discrete Three-Dimensional Architectures in Water. Angew Chem Int Ed Engl. 2018; 58(5):1280-1307. DOI: 10.1002/anie.201806297. View

19.

Jia P, Hu Y, Peng Z, Song B, Zeng Z, Ling Q . Construction of an Artificial Light-Harvesting System with Efficient Photocatalytic Activity in an Aqueous Solution Based on a FRET-Featuring Metallacage. Inorg Chem. 2022; 62(5):1950-1957. DOI: 10.1021/acs.inorgchem.2c01869. View

20.

Zhang Z, Zhao Z, Hou Y, Wang H, Li X, He G . Aqueous Platinum(II)-Cage-Based Light-Harvesting System for Photocatalytic Cross-Coupling Hydrogen Evolution Reaction. Angew Chem Int Ed Engl. 2019; 58(26):8862-8866. PMC: 6854906. DOI: 10.1002/anie.201904407. View