Organic conjugated polymers and polymer dots as photocatalysts for hydrogen production

Abstract

Owing to the outstanding characteristics of tailorable electronic and optical properties, semiconducting polymers have attracted considerable attention in recent years. Among them, organic polymer dots process large breadth of potential synthetic diversity are the representative of photocatalysts for hydrogen production, which presents both an opportunity and a challenge. In this mini-review, first, the organic polymer photocatalysts were introduced. Then, recent reports on polymer dots which showed a superior photocatalytic activity and a robust stability under visible-light irradiation, for hydrogen production were summarized. Finally, challenges and outlook on using organic polymer dots-based photocatalysts from hydrogen production were discussed.

Graphical abstract

Keywords

polymer dots (Pdots) / photocatalysis / hydrogen production

References

[1] Wang Y, Vogel A, Sachs M, . Current understanding and challenges of solar-driven hydrogen generation using polymeric photocatalysts. Nature Energy, 2019, 4(9): 746–760

[2] Kudo A, Miseki Y. Heterogeneous photocatalyst materials for water splitting. Chemical Society Reviews, 2009, 38(1): 253–278

[3] Fujishima A, Honda K. Electrochemical photolysis of water at a semiconductor electrode. Nature, 1972, 238(5358): 37–38

[4] Zou Z, Ye J, Sayama K, Arakawa H. Direct splitting of water under visible light irradiation with an oxide semiconductor photocatalyst. Nature, 2001, 414(6864): 625–627

[5] Turner J A. Sustainable hydrogen production. Science, 2004, 305(5686): 972–974

[6] Chen C, Ma W, Zhao J. Semiconductor-mediated photodegradation of pollutants under visible-light irradiation. Chemical Society Reviews, 2010, 39(11): 4206–4219

[7] Fajrina N, Tahir M. A critical review in strategies to improve photocatalytic water splitting towards hydrogen production. International Journal of Hydrogen Energy, 2019, 44(2): 540–577

[8] Zeng L, Guo X, He C, . Metal–organic frameworks: versatile materials for heterogeneous photocatalysis. ACS Catalysis, 2016, 6(11): 7935–7947

[9] Maeda K, Teramura K, Lu D, . Photocatalyst releasing hydrogen from water. Nature, 2006, 440(7082): 295

[10] Xie J, Shevlin S A, Ruan Q, . Efficient visible light-driven water oxidation and proton reduction by an ordered covalent triazine-based framework. Energy & Environmental Science, 2018, 11(6): 1617–1624

[11] Schultz D M, Yoon T P. Solar synthesis: prospects in visible light photocatalysis. Science, 2014, 343(6174): 1239176

[12] Xiao J D, Han L, Luo J, . Integration of plasmonic effects and schottky junctions into metal-organic framework composites: steering charge flow for enhanced visible-light photocatalysis. Angewandte Chemie International Edition, 2018, 57(4): 1103–1107

[13] Jin H, Liu X, Chen S, . Heteroatom-doped transition metal electrocatalysts for hydrogen evolution reaction. ACS Energy Letters, 2019, 4(4): 805–810

[14] Lu Q, Yu Y, Ma Q, . 2D transition-metal-dichalcogenide-nanosheet-based composites for photocatalytic and electrocatalytic hydrogen evolution reactions. Advanced Materials, 2016, 28(10): 1917–1933

[15] Zhang N, Wang L, Wang H, . Self-assembled one-dimensional porphyrin nanostructures with enhanced photocatalytic hydrogen generation. Nano Letters, 2018, 18(1): 560–566

[16] Kargar A, Jing Y, Kim S J, . ZnO/CuO heterojunction branched nanowires for photoelectrochemical hydrogen generation. ACS Nano, 2013, 7(12): 11112–11120

[17] Tao X, Zhao Y, Mu L, . Bismuth tantalum oxyhalogen: a promising candidate photocatalyst for solar water splitting. Advanced Energy Materials, 2018, 8(1): 1701392

[18] Woods D J, Sprick R S, Smith C L, . A solution-processable polymer photocatalyst for hydrogen evolution from water. Advanced Energy Materials, 2017, 7(22): 1700479

[19] Kuecken S, Acharjya A, Zhi L, . Fast tuning of covalent triazine frameworks for photocatalytic hydrogen evolution. Chemical Communications, 2017, 53(43): 5854–5857

[20] Chen H, Zheng X, Li Q, . An amorphous precursor route to the conformable oriented crystallization of CH₃NH₃PbBr₃ in mesoporous scaffolds: toward efficient and thermally stable carbon-based perovskite solar cells. Journal of Materials Chemistry A, Materials for Energy and Sustainability, 2016, 4(33): 12897–12912

[21] Zhou J, Lei Y, Ma C, . A (001) dominated conjugated polymer with high-performance of hydrogen evolution under solar light irradiation. Chemical Communications, 2017, 53(76): 10536–10539

[22] Wang X, Maeda K, Chen X, . Polymer semiconductors for artificial photosynthesis: hydrogen evolution by mesoporous graphitic carbon nitride with visible light. Journal of the American Chemical Society, 2009, 131(5): 1680–1681

[23] Wang X, Maeda K, Thomas A, . A metal-free polymeric photocatalyst for hydrogen production from water under visible light. Nature Materials, 2009, 8(1): 76–80

[24] Cao S, Yu J. g-C₃N₄-based photocatalysts for hydrogen generation. Journal of Physical Chemistry Letters, 2014, 5(12): 2101–2107

[25] Chen D, Wang K, Hong W, . Visible light photoactivity enhancement via CuTCPP hybridized g-C₃N₄ nanocomposite. Applied Catalysis B: Environmental, 2015, 166–167: 366–373

[26] Schwinghammer K, Tuffy B, Mesch M B, . Triazine-based carbon nitrides for visible-light-driven hydrogen evolution. Angewandte Chemie International Edition, 2013, 52(9): 2435–2439

[27] Masih D, Ma Y, Rohani S. Graphitic C₃N₄ based noble-metal-free photocatalyst systems: a review. Applied Catalysis B: Environmental, 2017, 206: 556–588

[28] Zhang M, Xu J, Zong R, . Enhancement of visible light photocatalytic activities via porous structure of g-C₃N₄. Applied Catalysis B: Environmental, 2014, 147: 229–235

[29] Guo Y, Chu S, Yan S, . Developing a polymeric semiconductor photocatalyst with visible light response. Chemical Communications, 2010, 46(39): 7325–7327

[30] Xing W, Tu W, Han Z, . Template-induced high-crystalline g-C₃N₄ nanosheets for enhanced photocatalytic H₂ evolution. ACS Energy Letters, 2018, 3(3): 514–519

[31] Zhang G, Lan Z A, Wang X. Conjugated polymers: catalysts for photocatalytic hydrogen evolution. Angewandte Chemie International Edition, 2016, 55(51): 15712–15727

[32] Vyas V S, Lau V W, Lotsch B V. Soft photocatalysis: organic polymers for solar fuel production. Chemistry of Materials, 2016, 28(15): 5191–5204

[33] Yu J, Rong Y, Kuo C T, . Recent advances in the development of highly luminescent semiconducting polymer dots and nanoparticles for biological imaging and medicine. Analytical Chemistry, 2017, 89(1): 42–56

[34] Li K, Liu B. Polymer-encapsulated organic nanoparticles for fluorescence and photoacoustic imaging. Chemical Society Reviews, 2014, 43(18): 6570–6597

[35] Guo L, Ge J, Wang P. Polymer dots as effective phototheranostic agents. Photochemistry and Photobiology, 2018, 94(5): 916–934

[36] Feng L, Zhu C, Yuan H, . Conjugated polymer nanoparticles: preparation, properties, functionalization and biological applications. Chemical Society Reviews, 2013, 42(16): 6620–6633

[37] Shirakawa H, Louis E J, MacDiarmid A G, . Synthesis of electrically conducting organic polymers: halogen derivatives of polyacetylene, (CH)_x. Journal of the Chemical Society. Chemical Communications, 1977, (16): 578–580

[38] Chiang C K, Fincher C R, Park Y W, . Electrical conductivity in doped polyacetylene. Physical Review Letters, 1977, 39(17): 1098–1101

[39] Wu C, Chiu D T. Highly fluorescent semiconducting polymer dots for biology and medicine. Angewandte Chemie International Edition, 2013, 52(11): 3086–3109

[40] Pei Q, Yu G, Zhang C, . Polymer light-emitting electrochemical cells. Science, 1995, 269(5227): 1086–1088

[41] Friend R H, Gymer R W, Holmes A B, . Electroluminescence in conjugated polymers. Nature, 1999, 397(6715): 121–128

[42] Müller C D, Falcou A, Reckefuss N, . Multi-colour organic light-emitting displays by solution processing. Nature, 2003, 421(6925): 829–833

[43] Wu H, Ying L, Yang W, . Progress and perspective of polymer white light-emitting devices and materials. Chemical Society Reviews, 2009, 38(12): 3391–3400

[44] Yu G, Gao J, Hummelen J C, . Polymer photovoltaic cells: enhanced efficiencies via a network of internal donor-acceptor heterojunctions. Science, 1995, 270(5243): 1789–1791

[45] Günes S, Neugebauer H, Sariciftci N S. Conjugated polymer-based organic solar cells. Chemical Reviews, 2007, 107(4): 1324–1338

[46] Burroughes J H, Jones C A, Friend R H. New semiconductor device physics in polymer diodes and transistors. Nature, 1988, 335(6186): 137–141

[47] Yang Y, Heeger A J. A new architecture for polymer transistors. Nature, 1994, 372(6504): 344–346

[48] Yan H, Chen Z, Zheng Y, . A high-mobility electron-transporting polymer for printed transistors. Nature, 2009, 457(7230): 679–686

[49] Zhang K, Monteiro M J, Jia Z. Stable organic radical polymers: synthesis and applications. Polymer Chemistry, 2016, 7(36): 5589–5614

[50] Reis M H, Leibfarth F A, Pitet L M. Polymerizations in continuous flow: recent advances in the synthesis of diverse polymeric materials. ACS Macro Letters, 2020, 9(1): 123–133

[51] Sprick R S, Jiang J X, Bonillo B, . Tunable organic photocatalysts for visible-light-driven hydrogen evolution. Journal of the American Chemical Society, 2015, 137(9): 3265–3270

[52] Maeda K, Domen K. New non-oxide photocatalysts designed for overall water splitting under visible light. Journal of Physical Chemistry C, 2007, 111(22): 7851–7861

[53] Kosco J, Sachs M, Godin R, . The effect of residual palladium catalyst contamination on the photocatalytic hydrogen evolution activity of conjugated polymers. Advanced Energy Materials, 2018, 8(34): 1802181

[54] Yanagida S, Kabumoto A, Mizumoto K, . Poly(p-phenylene)-catalysed photoreduction of water to hydrogen. Journal of the Chemical Society, Chemical Communications, 1985, (8): 474–475

[55] Schwab M G, Hamburger M, Feng X, . Photocatalytic hydrogen evolution through fully conjugated poly(azomethine) networks. Chemical Communications, 2010, 46(47): 8932–8934

[56] Shibata T, Kabumoto A, Shiragami T, . Novel visible-light-driven photocatalyst. Poly(p-phenylene)-catalyzed photoreductions of water, carbonyl compounds, and olefins. Journal of Physical Chemistry, 1990, 94(5): 2068–2076

[57] Zhang Z, Long J, Yang L, . Organic semiconductor for artificial photosynthesis: water splitting into hydrogen by a bioinspired C₃N₃S₃ polymer under visible light irradiation. Chemical Science (Cambridge), 2011, 2(9): 1826–1830

[58] Yamamoto T, Yoneda Y, Maruyama T. Ruthenium and nickel complexes of a π-conjugated electrically conducting polymer chelate ligand, poly(2,2′-bipyridine-5,5′-diyl), and their chemical and catalytic reactivity. Journal of the Chemical Society, Chemical Communications, 1992, 0(22): 1652–1654

[59] Maruyama T, Yamamoto T. Effective photocatalytic system based on chelating π-conjugated poly(2,2′-bipyridine-5,5′-diyl) and platinum for photoevolution of H₂ from aqueous media and spectroscopic analysis of the catalyst. Journal of Physical Chemistry B, 1997, 101(19): 3806–3810

[60] Kailasam K, Schmidt J, Bildirir H, . Room temperature synthesis of heptazine-based microporous polymer networks as photocatalysts for hydrogen evolution. Macromolecular Rapid Communications, 2013, 34(12): 1008–1013

[61] Kailasam K, Mesch M B, Möhlmann L, . Donor–acceptor-type heptazine-based polymer networks for photocatalytic hydrogen evolution. Energy Technology (Weinheim), 2016, 4(6): 744–750

[62] Li R, Byun J, Huang W, . Poly(benzothiadiazoles) and their derivatives as heterogeneous photocatalysts for visible-light-driven chemical transformations. ACS Catalysis, 2018, 8(6): 4735–4750

[63] Stegbauer L, Schwinghammer K, Lotsch B V. A hydrazone-based covalent organic framework for photocatalytic hydrogen production. Chemical Science (Cambridge), 2014, 5(7): 2789–2793

[64] Mukherjee G, Thote J, Aiyappa H B, . A porous porphyrin organic polymer (PPOP) for visible light triggered hydrogen production. Chemical Communications, 2017, 53(32): 4461–4464

[65] Huang X, Wu Z, Zheng H, . A sustainable method toward melamine-based conjugated polymer semiconductors for efficient photocatalytic hydrogen production under visible light. Green Chemistry, 2018, 20(3): 664–670

[66] Banerjee T, Haase F, Savasci G, . Single-site photocatalytic H₂ evolution from covalent organic frameworks with molecular cobaloxime Co-catalysts. Journal of the American Chemical Society, 2017, 139(45): 16228–16234

[67] Wang K, Yang L M, Wang X, . Covalent triazine frameworks via a low-temperature polycondensation approach. Angewandte Chemie International Edition, 2017, 56(45): 14149–14153

[68] Banerjee T, Gottschling K, Savasci G, . H₂ evolution with covalent organic framework photocatalysts. ACS Energy Letters, 2018, 3(2): 400–409

[69] Kosco J, McCulloch I. Residual Pd enables photocatalytic H₂ evolution from conjugated polymers. ACS Energy Letters, 2018, 3(11): 2846–2850

[70] Zhao P, Wang L, Wu Y, . Hyperbranched conjugated polymer dots: the enhanced photocatalytic activity for visible light-driven hydrogen production. Macromolecules, 2019, 52(11): 4376–4384

[71] Weber J, Thomas A. Toward stable interfaces in conjugated polymers: Microporous poly(p-phenylene) and poly(phenyleneethynylene) based on a spirobifluorene building block. Journal of the American Chemical Society, 2008, 130(20): 6334–6335

[72] Sprick R S, Bonillo B, Clowes R, . Visible-light-driven hydrogen evolution using planarized conjugated polymer photocatalysts. Angewandte Chemie International Edition, 2016, 55(5): 1792–1796

[73] Schwarze M, Stellmach D, Schröder M, . Quantification of photocatalytic hydrogen evolution. Physical Chemistry Chemical Physics, 2013, 15(10): 3466–3472

[74] Sprick R S, Aitchison C M, Berardo E, . Maximising the hydrogen evolution activity in organic photocatalysts by co-polymerisation. Journal of Materials Chemistry A, Materials for Energy and Sustainability, 2018, 6(25): 11994–12003

[75] Sprick R S, Wilbraham L, Bai Y, . Nitrogen containing linear poly(phenylene) derivatives for photo-catalytic hydrogen evolution from water. Chemistry of Materials, 2018, 30(16): 5733–5742

[76] Ting L Y, Jayakumar J, Chang C L, . Effect of controlling the number of fused rings on polymer photocatalysts for visible-light-driven hydrogen evolution. Journal of Materials Chemistry A, Materials for Energy and Sustainability, 2019, 7(40): 22924–22929

[77] Miao J, Li H, Wang T, . Donor–acceptor type conjugated copolymers based on alternating BNBP and oligothiophene units: from electron acceptor to electron donor and from amorphous to semicrystalline. Journal of Materials Chemistry A, Materials for Energy and Sustainability, 2020, 8(40): 20998–21006

[78] Vogel A, Forster M, Wilbraham L, . Photocatalytically active ladder polymers. Faraday Discussions, 2019, 215(0): 84–97

[79] Chen X, Li R, Liu Z, . Small photoblinking semiconductor polymer dots for fluorescence nanoscopy. Advanced Materials, 2017, 29(5): 1604850

[80] Moffitt M, Khougaz K, Eisenberg A. Micellization of ionic block copolymers. Accounts of Chemical Research, 1996, 29(2): 95–102

[81] Ye F, Wu C, Jin Y, . Ratiometric temperature sensing with semiconducting polymer dots. Journal of the American Chemical Society, 2011, 133(21): 8146–8149

[82] Chan Y H, Wu C, Ye F, . Development of ultrabright semiconducting polymer dots for ratiometric pH sensing. Analytical Chemistry, 2011, 83(4): 1448–1455

[83] Jiang Y, McNeill J. Light-harvesting and amplified energy transfer in conjugated polymer nanoparticles. Chemical Reviews, 2017, 117(2): 838–859

[84] Pu K, Shuhendler A J, Jokerst J V, . Semiconducting polymer nanoparticles as photoacoustic molecular imaging probes in living mice. Nature Nanotechnology, 2014, 9(3): 233–239

[85] Wu C, Schneider T, Zeigler M, . Bioconjugation of ultrabright semiconducting polymer dots for specific cellular targeting. Journal of the American Chemical Society, 2010, 132(43): 15410–15417

[86] Huang Y C, Chen C P, Wu P J, . Coumarin dye-embedded semiconducting polymer dots for ratiometric sensing of fluoride ions in aqueous solution and bio-imaging in cells. Journal of Materials Chemistry B, Materials for Biology and Medicine, 2014, 2(37): 6188–6191

[87] Guo L, Ge J, Wang P. Polymer dots as effective phototheranostic agents. Photochemistry and Photobiology, 2018, 94(5): 916–934

[88] Hassan A M, Wu X, Jarrett J W, . Polymer dots enable deep in vivo multiphoton fluorescence imaging of microvasculature. Biomedical Optics Express, 2019, 10(2): 584–599

[89] Jayakumar J, Chou H-H. Recent advances in visible-light-driven hydrogen evolution from water using polymer photocatalysts. ChemCatChem, 2020, 12(3): 689–704

[90] Dai C, Liu B. Conjugated polymers for visible-light-driven photocatalysis. Energy & Environmental Science, 2020, 13(1): 24–52

[91] Tseng P J, Chang C L, Chan Y H, . Design and synthesis of cycloplatinated polymer dots as photocatalysts for visible-light-driven hydrogen evolution. ACS Catalysis, 2018, 8(9): 7766–7772

[92] Wang L, Fernández-Terán R, Zhang L, . Organic polymer dots as photocatalysts for visible light-driven hydrogen generation. Angewandte Chemie International Edition, 2016, 55(40): 12306–12310

[93] Pati P B, Damas G, Tian L, . An experimental and theoretical study of an efficient polymer nano-photocatalyst for hydrogen evolution. Energy & Environmental Science, 2017, 10(6): 1372–1376

[94] Kaeffer N, Morozan A, Artero V. Oxygen tolerance of a molecular engineered cathode for hydrogen evolution based on a cobalt diimine–dioxime catalyst. Journal of Physical Chemistry B, 2015, 119(43): 13707–13713

[95] Liu A, Tai C W, Holá K, . Hollow polymer dots: nature-mimicking architecture for efficient photocatalytic hydrogen evolution reaction. Journal of Materials Chemistry A, Materials for Energy and Sustainability, 2019, 7(9): 4797–4803

[96] Zhang J, Chen X, Takanabe K, . Synthesis of a carbon nitride structure for visible-light catalysis by copolymerization. Angewandte Chemie International Edition, 2010, 49(2): 441–444

[97] Chang C L, Lin W C, Jia C Y, . Low-toxic cycloplatinated polymer dots with rational design of acceptor co-monomers for enhanced photocatalytic efficiency and stability. Applied Catalysis B: Environmental, 2020, 268: 118436

[98] Hu Z, Wang Z, Zhang X, . Conjugated polymers with oligoethylene glycol side chains for improved photocatalytic hydrogen evolution. iScience, 2019, 13: 33–42

[99] Rafiq M, Chen Z, Tang H, . Water–alcohol-soluble hyperbranched polyelectrolytes and their application in polymer solar cells and photocatalysis. ACS Applied Polymer Materials, 2020, 2(1): 12–18

[100] Hu Z, Zhang X, Yin Q, . Highly efficient photocatalytic hydrogen evolution from water-soluble conjugated polyelectrolytes. Nano Energy, 2019, 60: 775–783

[101] Zhou W, Jia T, Shi H, . Conjugated polymer dots/graphitic carbon nitride nanosheet heterojunctions for metal-free hydrogen evolution photocatalysis. Journal of Materials Chemistry A, Materials for Energy and Sustainability, 2019, 7(1): 303–311

RIGHTS & PERMISSIONS

Higher Education Press