Polymer-based chromophore–catalyst assemblies for solar energy conversion
© The Author(s) 2017
Received: 8 November 2017
Accepted: 7 December 2017
Published: 22 December 2017
The synthesis of polymer-based assemblies for light harvesting has been motivated by the multi-chromophore antennas that play a role in natural photosynthesis for the potential use in solar conversion technologies. This review describes a general strategy for using polymer-based chromophore–catalyst assemblies for solar-driven water oxidation at a photoanode in a dye-sensitized photoelectrochemical cell (DSPEC). This report begins with a summary of the synthetic methods and fundamental photophysical studies of light harvesting polychormophores in solution which show these materials can transport excited state energy to an acceptor where charge-separation can occur. In addition, studies describing light harvesting polychromophores containing an anchoring moiety (ionic carboxylate) for covalent bounding to wide band gap mesoporous semiconductor surfaces are summarized to understand the photophysical mechanisms of directional energy flow at the interface. Finally, the performance of polychromophore/catalyst assembly-based photoanodes capable of light-driven water splitting to oxygen and hydrogen in a DSPEC are summarized.
Artificial photosynthesis mimics the natural process occurring in plants with specifically engineered light-harvesting systems to carry out the direct transformation of light energy to that stored in a chemical bond (i.e. a solar fuel) . The ultimate goal in artificial photosynthesis is to generate carbon-based fuels from water splitting and CO2 reduction with sunlight as shown in Eq 1 .
In natural photosynthesis, a multi-chromophore antenna system absorbs light efficiently and transmits excited-state energy rapidly to a reaction center. Related antenna strategies can be achieved with polychromophoric polymers. Ruthenium(II) polypyridyl complexes have been widely used over the last decades as light harvesting chromophores due to their high absorptivity in the visible spectrum for a strong metal-to-ligand charge transfer (MLCT) transition [11, 14–17]. Ruthenium(II) polypyridine complexes incorporated into a polymer scaffold offer a potential means of developing light-harvesting antenna systems for applications in dye-sensitized photovoltaic cells and artificial photosynthesis. According to previous studies, MLCT excitons in polymeric chromophore systems exhibit a site-to-site hoping mechanism along the polymer chains [18, 19]. In the past several decades there have been a number of reported polymeric chromophore systems containing pendant ruthenium(II) polypyridine as light harvesting units because of beneficial properties such as remarkable photo- and thermal stability and long-distance exciton and charge transport [20–25]. Recently, our research group has carried out investigations of the photophysical and electrochemical properties of novel polychromophores or polychromophore–catalyst assemblies in order to understand the photodynamics of charge and exciton transport in solution and at the interface of semiconductor materials [19, 26, 27].
Constructing films of defined molecular composition has been a priority of applied material and interface science. Layer-by-layer (LbL) polyelectrolyte self-assembly offers a simple and versatile tool to allow facile control of molecular assemblies prepared directly on substrate films . Most LbL polyelectrolyte films feature multilayers composed of positively and negatively charged polyelectrolytes and employ the electrostatic Coulomb interaction between the oppositely charged macromolecules to form stable films. LbL technology has promising applications in solid-state light-emitting devices , drug delivery , biomembrane , electrodialysis membranes , and diagnostics . Very recently, Leem et al. used the LbL approach to construct multilayers for the use in a DSPEC .
This review is focused on the synthesis, and photophysical properties of polymeric assemblies consisting of multiple Ru(II) polypyridyl complexes as well as the polyelectrolyte LbL chromophore–catalyst assembly deposited onto semiconductor substrates for use in a DSPEC. The review highlights light-driven water oxidation using a polymeric chromophore–catalyst assembly immobilized onto a semiconductor at a DSPEC photoanode.
2 Polymer-based metal complex assemblies
2.1 Synthesis and characterization of polymer-based metal complex assemblies
Our research group has been interested in developing polymerization strategies to prepare functionalized polystyrenes that feature pendant metal–organic chromophores and to investigate the photophysical and electrochemical properties of the chromophoric sites preserved in the polymer. As an early synthetic strategy, polymer assemblies containing a [tris(bipyridyl)ruthenium(II) derivatives] were considered for creating polymer assemblies that could be modified by introducing polypyridyl Ru complexes [24, 25, 34].
The polymer poly(4(2-[N,N-bis(trimethylsilyl)amino]ethyl)styrene) (4) was prepared by a living anionic polymerization method that offers well-controlled polymer chain lengths and narrow polydispersity (Mw/Mn < 1.2) compared to the previous polymer (3) that was prepared by free radical polymerization and had a PDI of 1.5 . The amide coupling reaction was carried out to link a ruthenium polypyridyl complex to the amino polymer. A major drawback of this anionic polymerization is monomer functional group tolerance under the strongly basic reaction conditions. As a key advantage, however, that aids the investigations of the photophysical properties of the polymer, the amino polymers synthesized by this method are linear and optically transparent in the visible region.
Our group reported the synthesis of a polystyrene backbone by the reversible addition-fragmentation chain transfer (RAFT) polymerization method combined with the azide-alkyne Huisgen cycloaddition as a “click chemistry” reaction . The azide-alkyne click reaction affords a high yield for grafting Ru(II) complexes containing a terminal acetylene group onto the methyl azide functionalized polystyrene backbone. This is followed by the formation of a triazole linker under mild reaction conditions at room temperature. From emission quantum yield and lifetime studies, the MLCT excited state is efficiently quenched in the RAFT PS-Ru polychromophores (5) relative to a model Ru complex chromophore in the absence of a polymer backbone. Interestingly, the thiol (–SH) end-groups on the polymers from the RAFT chain transfer agent can quench the MLCT state by a charge-transfer mechanism among the chromophore, leading to considerable reduction in the lifetime of the MLCT state.
Recently, in order to eliminate the thiol polymer end-groups we developed atom transfer radical polymerization (ATRP) and nitroxide-mediated controlled radical polymerization (NMP) methods to prepare polystyrene-based polychromophores with pendant Ru(II) polypyridyl complexes [18, 20, 21, 23]. The ATRP method allows for postpolymerization modification by incorporating –Br end group functionality . The polypyridylruthenium derivatized polystyrenes were achieved in two steps. The polystyrene backbone was prepared by ATRP of the N-hydroxyscuccinimide (NHS) derivative of 4-vinyl benzoate with methyl α-bromoisobutyrate as the initiator. Subsequently an amide coupling reaction of the NHS-polystyrene with Ru(II) complexes derivatized with aminomethyl groups ([Ru(bpy)2(CH3-bpy-CH2NH2)]2+) afforded polypyridylruthenium derivatized polystyrenes, (6).
2.2 Polymeric chromophores on metal oxide films
3 Polymer chromophore–catalyst assemblies for solar energy conversion
Using the C–G setup, it was shown that the PS-Ru/RuC LbL system could carry out light driven water oxidation at a SnO2/TiO2 core/shell electrode with the best performance observed for FTO//(SnO2/TiO2)//(PAA/PS-Ru)5/(PAA/RuC)5 . The photocurrent density of this photoanode was ca. 10 μA cm−2 after 30 s of illumination (0.44 V vs. NHE bias) and the C–G analysis showed the generation of O2 with a 22% Faradaic efficiency. This performance mirrored other DSPEC studies using the same RuC catalyst with more modest overall photocurrent densities than observed compared to the use of [Ru(bda)(L)2]-type water oxidation catalysts (bda = 2,2′-bipyridine-6,6′-dicarboxylate; L = neutral donor ligand) [51–53]. The performance of the PS-Ru/RuC LbL system did demonstrate the viability of this approach for to preparing photoelectrode interfaces and improvement will likely occur through further optimization of the LbL deposition strategy and introduction of more active molecular catalysts such as [Ru(bda)(L)2].
Electrochemical analysis of poly-2 showed behavior characteristic of both the Ru-C and Ru-Cat subunits (Fig. 8b). While the poly-2 shows an anodic wave for the RuIII/II couple of the Ru-C component at 1.2 V vs NHE and a catalytic wave at Eapp > 1.4 V vs NHE characteristic of Ru-Cat, the oxidation of the Ru-C is irreversible in the polymer. This was taken as evidence for hole transfer from Ru-C III to Ru-Cat within the polymer structure. FTO//nanoTiO2 photoanodes with 10 LbL layers of PAA/poly-2 were active for the light driven oxidation of phenol or benzyl alcohol, with the photocurrent response increasing with an increase in concentration of the organic substrate (Fig. 8c). Light driven water oxidation was investigated with 5 LbL layer thick polyacrylic acid (PAA)/poly-2 on FTO//(SnO2/TiO2) core/shell electrodes (FTO//(SnO2/TiO2)//(PAA/poly-2)5) which gave a twofold enhanced photocurrent response compared to FTO//(SnO2/TiO2)//(PAA/poly-1)5 (poly-1 containing only Ru-C with no Ru-Cat moieties present in the polymer). This was taken as likely evidence for light driven water oxidation though the generation of O2 was not quantified.
In this review, we summarize a series of polymeric assemblies consisting of multiple Ru(II) polypyridyl complexes prepared by using several polymerization methods including living anionic polymerization, RAFT, ATRP and NMP, followed by postreaction such as amidation reaction and click chemistry for the attachment of Ru(II) polypyridyl complexes to the polymer backbone. We describe the structure and dynamics of these polymer assemblies on mesoporous structure semiconductor films. Polymeric chromophore–catalyst assembly specifically containing chromophore units and an oxidation catalyst was developed to demonstrate its use in light-driven water oxidation at a photoanode-solution interface for a DSPEC application.
All authors have contributed to the writing of the manuscript. All authors read and approved the final manuscript.
The authors declare that they have no competing interests.
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This material is based on work supported solely as part of the UNC EFRC: Solar Fuels and Next Generation Photovoltaics, an Energy Frontier Research Center funded by the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences under Award Number DE-SC0001011.
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