Visible-light photoredox catalysis with organic polymers

The development of photocatalysts to drive organic reactions is a frontier research topic. Organic polymers can be well tuned in terms of structural and photophysical properties and, therefore, constitute a promising class of photocatalysts in photoredox catalysis for organic synthesis. In this review article, we provide an overview of the concept of photoredox catalysis and recent developments in organic polymers as photocatalysts including porous organic polymers, graphitic carbon nitride, carbon dots, and polymer dots with adjustable reactivity that have undergone state-of-the-art advancement in different photoredox catalytic organic reactions.

[1]  A. Saravanan,et al.  Recent advances in polymer composite, extraction, and their application for wastewater treatment: A review. , 2022, Chemosphere.

[2]  W. Gao,et al.  Alkali metal modified carbon nitride enhance photocatalytic performance for highly selective oxidation of benzyl C(sp)-H bonds , 2022, Applied Catalysis B: Environmental.

[3]  T. Swager,et al.  Solution-processable microporous polymer platform for heterogenization of diverse photoredox catalysts , 2022, Nature Communications.

[4]  C. Turro,et al.  Two-photon-absorbing ruthenium complexes enable near infrared light-driven photocatalysis , 2022, Nature Communications.

[5]  Hongwei Huang,et al.  Solar Energy Catalysis , 2022, Angewandte Chemie.

[6]  Reiner Sebastian Sprick,et al.  Reconstructed covalent organic frameworks , 2022, Nature.

[7]  Xiaozhou Huang,et al.  Phenylphenothiazine-Based Porous Organic Polymers as Visible-Light Heterogeneous Photocatalysts for Switchable Bromoalkylation and Cyclopropanation of Unactivated Terminal Alkenes , 2022, ACS Sustainable Chemistry & Engineering.

[8]  H. Tian,et al.  Efficient Generation of Hydrogen Peroxide and Formate by an Organic Polymer Dots Photocatalyst in Alkaline Conditions , 2022, Angewandte Chemie.

[9]  R. Sougrat,et al.  Generation of long-lived charges in organic semiconductor heterojunction nanoparticles for efficient photocatalytic hydrogen evolution , 2022, Nature Energy.

[10]  Hui Song,et al.  Solar-Driven Hydrogen Production: Recent Advances, Challenges, and Future Perspectives , 2022, ACS Energy Letters.

[11]  Y. Liao,et al.  Macroscale Conjugated Microporous Polymers: Controlling Versatile Functionalities Over Several Dimensions , 2022, Advanced materials.

[12]  O. Farha,et al.  Porous materials for hydrogen storage , 2022, Chem.

[13]  Shufang Liu,et al.  Multifunctional covalent organic frameworks for photocatalytic oxidative hydroxylation of arylboronic acids and fluorescence sensing for Cu2+ , 2022, Microporous and Mesoporous Materials.

[14]  Wenping Hu,et al.  2D Covalent Organic Frameworks: From Synthetic Strategies to Advanced Optical‐Electrical‐Magnetic Functionalities , 2022, Advanced materials.

[15]  J. Mondal,et al.  Nanoarchitectonics of Metal-Free Porous Polyketone as Photocatalytic Assemblies for Artificial Photosynthesis. , 2021, ACS applied materials & interfaces.

[16]  Xianjun Lang,et al.  Selective photocatalytic formation of sulfoxides by aerobic oxidation of sulfides over conjugated microporous polymers with thiazolo[5,4‑d]thiazole linkage , 2021 .

[17]  H. Tan,et al.  Design of porous organic polymer photocatalysts based on heptazine for efficient photocatalytic aerobic oxidation , 2021, Chemical Engineering Journal.

[18]  S. Ott,et al.  Catalytic systems mimicking the [FeFe]-hydrogenase active site for visible-light-driven hydrogen production , 2021, Coordination Chemistry Reviews.

[19]  Jianfeng Ping,et al.  Recent Advances in g-C3 N4 -Based Photocatalysts for Pollutant Degradation and Bacterial Disinfection: Design Strategies, Mechanisms, and Applications. , 2021, Small.

[20]  Dengxu Wang,et al.  Fluorescent Hybrid Porous Polymers as Sustainable Heterogeneous Photocatalysts for Cross-Dehydrogenative Coupling Reactions. , 2021, ACS applied materials & interfaces.

[21]  I. Pinnau,et al.  Recent Progress on Polymers of Intrinsic Microporosity and Thermally Modified Analogue Materials for Membrane‐Based Fluid Separations , 2021, Small Structures.

[22]  S. Pal,et al.  A Dual-Function Highly Crystalline Covalent Organic Framework for HCl Sensing and Visible-Light Heterogeneous Photocatalysis , 2021, Macromolecules.

[23]  I. Hussain,et al.  Immobilized covalent triazine frameworks films as effective photocatalysts for hydrogen evolution reaction , 2021, Nature Communications.

[24]  Xuanjun Zhang,et al.  Enhanced reduction of p-nitrophenol by zerovalent iron modified with carbon quantum dots , 2021 .

[25]  G. Zeng,et al.  Recent progress in conjugated microporous polymers for clean energy: Synthesis, modification, computer simulations, and applications , 2021 .

[26]  Z. Wang,et al.  Covalent Triazine Frameworks as Emerging Heterogeneous Photocatalysts , 2021 .

[27]  Siyu Lu,et al.  Efficient Combination of G-C3 N4 and CDs for Enhanced Photocatalytic Performance: A Review of Synthesis, Strategies, and Applications. , 2021, Small.

[28]  Bao-hang Han,et al.  Porous Organic Polymers for Photocatalytic Carbon Dioxide Reduction , 2021 .

[29]  R. Leblanc,et al.  A deep investigation into the structure of carbon dots , 2021, Carbon.

[30]  Fei Zhao,et al.  Eosin Y as a direct hydrogen-atom transfer photocatalyst for the C3-H acylation of quinoxalin-2(1H)-ones , 2021 .

[31]  K. Edwards,et al.  Panchromatic Ternary Polymer Dots Involving Sub-Picosecond Energy and Charge Transfer for Efficient and Stable Photocatalytic Hydrogen Evolution , 2021, Journal of the American Chemical Society.

[32]  S. Neogi,et al.  Dual-catalyst engineered porous organic framework for visible-light triggered, metal-free and aerobic sp3 C H activation in highly synergistic and recyclable fashion , 2021 .

[33]  C. Petit,et al.  Hypercrosslinked Polymers as a Photocatalytic Platform for Visible‐Light‐Driven CO2 Photoreduction Using H2O , 2020, ChemSusChem.

[34]  Renjith S Pillai,et al.  Structural engineering in pre-functionalized, imine-based covalent organic framework via anchoring active Ru(II)-complex for visible-light triggered and aerobic cross-coupling of α-amino esters with indoles , 2021 .

[35]  Vijay K. Tomer,et al.  State-of-the-art review of morphological advancements in graphitic carbon nitride (g-CN) for sustainable hydrogen production , 2021 .

[36]  F. Marken,et al.  Polymers of Intrinsic Microporosity in the Design of Electrochemical Multicomponent and Multiphase Interfaces. , 2020, Analytical chemistry.

[37]  Dengxu Wang,et al.  Phenazine Radical Cations as Efficient Homogeneous and Heterogeneous Catalysts for the Cross‐Dehydrogenative Aza‐ Henry Reaction , 2020 .

[38]  Yanjun Xie,et al.  Visible-light-enabled regioselective aerobic oxidative C(sp2)-H thiocyanation of aromatic compounds by Eosin-Y photocatalyst , 2020 .

[39]  M. Antonietti,et al.  Photocatalytic (Het)arylation of C(sp3)–H Bonds with Carbon Nitride , 2020, ACS Catalysis.

[40]  Hongbing Ji,et al.  Covalent Triazine Frameworks Obtained from Task-Specific Nitrile Monomers for Sustainable CO2 Catalysis. , 2020, ChemSusChem.

[41]  K. Domen,et al.  Visible-Light-Driven Photocatalytic Water Splitting: Recent Progress and Challenges , 2020 .

[42]  S. Phanichphant,et al.  Photocatalytic activity enhancement of g-C3N4/BiOBr in selective transformation of primary amines to imines and its reaction mechanism , 2020 .

[43]  Ye Yuan,et al.  Multifunctional porous aromatic frameworks: State of the art and opportunities , 2020 .

[44]  Huan‐Tsung Chang,et al.  Recent Advances and Sensing Applications of Carbon Dots , 2020 .

[45]  Jianrong Chen,et al.  Recent developments of doped g-C3N4 photocatalysts for the degradation of organic pollutants , 2020 .

[46]  G. Zhu,et al.  Porous Aromatic Frameworks (PAFs). , 2020, Chemical reviews.

[47]  R. Sougrat,et al.  Enhanced photocatalytic hydrogen evolution from organic semiconductor heterojunction nanoparticles , 2020, Nature Materials.

[48]  A. Cooper,et al.  Advances in Conjugated Microporous Polymers , 2020, Chemical reviews.

[49]  T. He,et al.  Covalent Organic Frameworks: Design, Synthesis, and Functions. , 2020, Chemical reviews.

[50]  Bing Liu,et al.  Carbon quantum dots @ Pd-SnS2 nanocomposite: The role of CQDs @ Pd nanoclusters in enhancing photocatalytic reduction of aromatic nitro compounds. , 2019, Journal of colloid and interface science.

[51]  Xue-Bo Yin,et al.  Carbon Dots, Unconventional Preparation Strategies, and Applications Beyond Photoluminescence. , 2019, Small.

[52]  Reiner Sebastian Sprick,et al.  Current understanding and challenges of solar-driven hydrogen generation using polymeric photocatalysts , 2019, Nature Energy.

[53]  S. Basu,et al.  Graphitic carbon nitride (g–C3N4)–based metal-free photocatalysts for water splitting: A review , 2019, Carbon.

[54]  A. Habibi-Yangjeh,et al.  Fabrication of novel ZnO/BiOBr/C-Dots nanocomposites with considerable photocatalytic performances in removal of organic pollutants under visible light , 2019, Advanced Powder Technology.

[55]  Eun Ho Choi,et al.  Hyper-Cross-Linked Polymer on the Hollow Conjugated Microporous Polymer Platform: A Heterogeneous Catalytic System for Poly(caprolactone) Synthesis. , 2019, ACS macro letters.

[56]  F. R. Pomilla,et al.  Photoelectrochemical and EPR features of polymeric C3N4 and O-modified C3N4 employed for selective photocatalytic oxidation of alcohols to aldehydes , 2019, Catalysis Today.

[57]  Hong Xia,et al.  Construction of donor-acceptor type conjugated microporous polymers: A fascinating strategy for the development of efficient heterogeneous photocatalysts in organic synthesis , 2019, Applied Catalysis B: Environmental.

[58]  Wenjun Jiang,et al.  Three-dimensional porous g-C3N4 for highly efficient photocatalytic overall water splitting , 2019, Nano Energy.

[59]  R. Banerjee,et al.  Triazine Functionalized Porous Covalent Organic Framework for Photo-organocatalytic E- Z Isomerization of Olefins. , 2019, Journal of the American Chemical Society.

[60]  Ling Zhang,et al.  High Selective Oxidation of Benzyl Alcohol to Benzylaldehyde and Benzoic Acid with Surface Oxygen Vacancies on W18O49/Holey Ultrathin g-C3N4 Nanosheets , 2019, ACS Sustainable Chemistry & Engineering.

[61]  Rui Wang,et al.  Synthesis of silica@C-dots/phosphotungstates core-shell microsphere for effective oxidative-adsorptive desulfurization of dibenzothiophene with less oxidant , 2018, Applied Catalysis B: Environmental.

[62]  M. Antonietti,et al.  Heterogeneous Organocatalysis for Photoredox Chemistry , 2018, ACS Catalysis.

[63]  Shaoming Huang,et al.  Carbon quantum dots/Zn2+ ions doped-CdS nanowires with enhanced photocatalytic activity for reduction of 4-nitroaniline to p-phenylenediamine , 2018, Applied Surface Science.

[64]  Weijie Zhang,et al.  Visible Light-Driven C-3 Functionalization of Indoles over Conjugated Microporous Polymers , 2018, ACS Catalysis.

[65]  Qianqian Liu,et al.  Insights into the Relationship of the Heterojunction Structure and Excellent Activity: Photo-Oxidative Coupling of Benzylamine on CeO2-rod/g-C3N4 Hybrid under Mild Reaction Conditions , 2018, ACS Sustainable Chemistry & Engineering.

[66]  K. Kailasam,et al.  Natural Sunlight Driven Oxidative Homocoupling of Amines by a Truxene-Based Conjugated Microporous Polymer , 2018, ACS Catalysis.

[67]  Quanjun Xiang,et al.  Enhanced photocatalytic H2-production activity of C-dots modified g-C3N4/TiO2 nanosheets composites. , 2018, Journal of colloid and interface science.

[68]  Rui Cao,et al.  Solar‐to‐Hydrogen Energy Conversion Based on Water Splitting , 2018 .

[69]  Jianghong Rao,et al.  Recent progress on semiconducting polymer nanoparticles for molecular imaging and cancer phototherapy. , 2018, Biomaterials.

[70]  S. Turner,et al.  Hypercrosslinked Polymers: A Review , 2018 .

[71]  J. R. García,et al.  Selective photocatalytic oxidation of aromatic alcohols in water by using P-doped g-C3N4 , 2018 .

[72]  G. Zeng,et al.  Doping of graphitic carbon nitride for photocatalysis: A reveiw , 2017 .

[73]  Yihe Zhang,et al.  Precursor-reforming protocol to 3D mesoporous g-C3N4 established by ultrathin self-doped nanosheets for superior hydrogen evolution , 2017 .

[74]  K. Landfester,et al.  Visible-Light-Promoted Selective Oxidation of Alcohols Using a Covalent Triazine Framework , 2017 .

[75]  Wei You,et al.  Hierarchical Porous O-Doped g-C3 N4 with Enhanced Photocatalytic CO2 Reduction Activity. , 2017, Small.

[76]  O. Yaghi,et al.  The atom, the molecule, and the covalent organic framework , 2017, Science.

[77]  Wei Che,et al.  Fast Photoelectron Transfer in (Cring)-C3N4 Plane Heterostructural Nanosheets for Overall Water Splitting. , 2017, Journal of the American Chemical Society.

[78]  R. Srivastava,et al.  An Efficient, Visible Light Driven, Selective Oxidation of Aromatic Alcohols and Amines with O2 Using BiVO4/g-C3N4 Nanocomposite: A Systematic and Comprehensive Study toward the Development of a Photocatalytic Process , 2017 .

[79]  C. Tung,et al.  Smart Utilization of Carbon Dots in Semiconductor Photocatalysis , 2016, Advanced materials.

[80]  Lei Wang,et al.  Organic Polymer Dots as Photocatalysts for Visible Light-Driven Hydrogen Generation. , 2016, Angewandte Chemie.

[81]  J. Scaiano,et al.  Library of Cationic Organic Dyes for Visible-Light-Driven Photoredox Transformations , 2016, ACS omega.

[82]  David A. Nicewicz,et al.  Organic Photoredox Catalysis. , 2016, Chemical reviews.

[83]  O. Ishitani,et al.  Iridium(III) 1-Phenylisoquinoline Complexes as a Photosensitizer for Photocatalytic CO2 Reduction: A Mixed System with a Re(I) Catalyst and a Supramolecular Photocatalyst. , 2016, Inorganic chemistry.

[84]  Siang-Piao Chai,et al.  Graphitic Carbon Nitride (g-C3N4)-Based Photocatalysts for Artificial Photosynthesis and Environmental Remediation: Are We a Step Closer To Achieving Sustainability? , 2016, Chemical reviews.

[85]  Bingbing Tian,et al.  Visible-Light Photocatalysis of Aerobic Oxidation Reactions Using Carbazolic Conjugated Microporous Polymers , 2016 .

[86]  H. Zeng,et al.  Remedying Defects in Carbon Nitride To Improve both Photooxidation and H2 Generation Efficiencies , 2016 .

[87]  Zhenzhen Lin,et al.  Condensed and low-defected graphitic carbon nitride with enhanced photocatalytic hydrogen evolution under visible light irradiation , 2016 .

[88]  Jiaguo Yu,et al.  Sulfur-doped g-C3N4 with enhanced photocatalytic CO2-reduction performance , 2015 .

[89]  K. Landfester,et al.  Conjugated Microporous Poly(Benzochalcogenadiazole)s for Photocatalytic Oxidative Coupling of Amines under Visible Light. , 2015, ChemSusChem.

[90]  X. Qu,et al.  Recent advances in bioapplications of C-dots , 2015 .

[91]  Jian Zhang,et al.  Carbazolic Porous Organic Framework as an Efficient, Metal-Free Visible-Light Photocatalyst for Organic Synthesis , 2015 .

[92]  Kyoung-Shin Choi,et al.  Combined biomass valorization and hydrogen production in a photoelectrochemical cell. , 2015, Nature chemistry.

[93]  M. Tan,et al.  Presence of photoluminescent carbon dots in Nescafe® original instant coffee: applications to bioimaging. , 2014, Talanta.

[94]  Qihua Wang,et al.  Amorphous covalent triazine frameworks for high performance room temperature ammonia gas sensing , 2014 .

[95]  Xiujian Zhao,et al.  Thermodynamic and kinetic analysis of heterogeneous photocatalysis for semiconductor systems. , 2014, Physical Chemistry, Chemical Physics - PCCP.

[96]  Changqin Ding,et al.  Functional surface engineering of C-dots for fluorescent biosensing and in vivo bioimaging. , 2014, Accounts of chemical research.

[97]  A. Cooper,et al.  Post-synthetic modification of conjugated microporous polymers , 2014 .

[98]  Jianhua Wang,et al.  Growth and stabilization of silver nanoparticles on carbon dots and sensing application. , 2013, Langmuir : the ACS journal of surfaces and colloids.

[99]  A. Nagai,et al.  Conjugated microporous polymers: design, synthesis and application. , 2013, Chemical Society reviews.

[100]  J. Scaiano,et al.  Mechanistic insights and kinetic analysis for the oxidative hydroxylation of arylboronic acids by visible light photoredox catalysis: a metal-free alternative. , 2013, Journal of the American Chemical Society.

[101]  D. MacMillan,et al.  Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis. , 2013, Chemical reviews.

[102]  M. Antonietti,et al.  Facilitating room-temperature Suzuki coupling reaction with light: Mott-Schottky photocatalyst for C-C-coupling , 2013, Scientific Reports.

[103]  Hui Huang,et al.  Near-infrared light controlled photocatalytic activity of carbon quantum dots for highly selective oxidation reaction. , 2013, Nanoscale.

[104]  Choon‐Hong Tan,et al.  Organic Dye‐Photocatalyzed Acylnitroso Ene Reaction , 2013 .

[105]  H. Ming,et al.  Large scale electrochemical synthesis of high quality carbon nanodots and their photocatalytic property. , 2012, Dalton transactions.

[106]  Yong Wang,et al.  Polymeric graphitic carbon nitride as a heterogeneous organocatalyst: from photochemistry to multipurpose catalysis to sustainable chemistry. , 2012, Angewandte Chemie.

[107]  P. Lianos,et al.  Photocatalysis and photoelectrocatalysis using (CdS-ZnS)/TiO2 combined photocatalysts , 2011 .

[108]  Markus Antonietti,et al.  mpg-C(3)N(4)-Catalyzed selective oxidation of alcohols using O(2) and visible light. , 2010, Journal of the American Chemical Society.

[109]  Ya‐Ping Sun,et al.  Bandgap-like strong fluorescence in functionalized carbon nanoparticles. , 2010, Angewandte Chemie.

[110]  M. A. Ischay,et al.  Visible light photocatalysis as a greener approach to photochemical synthesis. , 2010, Nature chemistry.

[111]  M. Antonietti,et al.  Fe-g-C3N4-catalyzed oxidation of benzene to phenol using hydrogen peroxide and visible light. , 2009, Journal of the American Chemical Society.

[112]  M. Antonietti,et al.  A metal-free polymeric photocatalyst for hydrogen production from water under visible light. , 2009, Nature materials.

[113]  R. Schlögl,et al.  Graphitic carbon nitride materials: variation of structure and morphology and their use as metal-free catalysts , 2008 .

[114]  Saad Makhseed,et al.  Polymers of intrinsic microporosity (PIMs): robust, solution-processable, organic nanoporous materials. , 2004, Chemical communications.

[115]  D. Frąckowiak.  The Jablonski diagram , 1988 .

[116]  E. C. Franklin.  THE AMMONO CARBONIC ACIDS , 1922 .

[117]  J. Liebig.  Uber einige Stickstoff ‐ Verbindungen , 1834 .

[118]  Jingsan Xu,et al.  Enhanced support effects in single-atom copper-incorporated carbon nitride for photocatalytic suzuki cross-coupling reactions , 2022, Applied Catalysis B: Environmental.