Photoanodes for water oxidation with visible light based on a pentacyclic quinoid organic dye enabling proton-coupled electron transfer

Volpato, Giulia Alice; Marasi, Martina; Gobbato, Thomas; Valentini, Francesca; Sabuzi, Federica; Gagliardi, Valeria; Bonetto, Alessandro; Marcomini, Antonio; Berardi, Serena; Conte, Valeria; Bonchio, Marcella; Caramori, Stefano; Galloni, Pierluca; Sartorel, Andrea

doi:10.1039/c9cc09805d

Cited by 22 publications

(45 citation statements)

References 40 publications

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“…Thus, future research strategies on molecular WOCs will move towards their immobilization on heterogeneous surfaces to avoid the limitations of conventional solution-based approaches. [144][145][146] 1.3. The importance of molecular integrity 1.3.1.…”

Section: Chem Soc Rev Review Articlementioning

confidence: 99%

Molecular and heterogeneous water oxidation catalysts: recent progress and joint perspectives

et al. 2021

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Section: Chem Soc Rev Review Articlementioning

confidence: 99%

Molecular and heterogeneous water oxidation catalysts: recent progress and joint perspectives

et al. 2021

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“…Such application demonstrated KuQ’s capability to manage proton-coupled electron transfer, thus leading to very good results in terms of faradaic efficiency of the cell. 19 …”

Section: Introductionmentioning

confidence: 99%

Unveiling KuQuinone Redox Species: An Electrochemical and Computational Cross Study

et al. 2021

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The study of the electrochemical properties of variegated quinones is a fascinating topic in chemistry. In fact, redox reactions occurring with quinoid scaffolds are essential for most of their applications in biological systems, in photoelectrochemical devices, and in many other fields. In this paper, a detailed investigation of KuQuinones’ redox behavior is presented. The distinctiveness of such molecules is the presence in the structure of two condensed naphthoquinone units, which implies the possibility to undergo multiple one-electron reduction processes. Solvent, supporting electrolyte, and hydrogen bond donor species effects have been elucidated. Changing the experimental parameters provoked significant shift of the redox potential for each reduction process. In particular, additions of 2,2,2-trifluoroethanol as a hydrogen bond donor in solution as well as Lewis acid coordination were crucial to obtain important shifts of the redox potentials toward more favorable values. UV–vis–NIR spectroelectrochemical experiments and DFT calculations are also presented to clarify the nature of the reduced species in solution.

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“…KuQ synthesis was executed following the previously reported one-pot procedure [32], in which 2-hydroxy-1,4-naphthoquinone is reacted with an excess of an appropriate alkyl bromide, in the presence of a base and ferrocene (FcH) in catalytic amount (Scheme 4). Overall, three KuQuinone phosphonate derivatives, differing in side-chain length, were synthesized with yields (7 to 11%, Table 2) that compare well with that of other KuQuinone analogues [29,30,33]. To achieve KuQuinone phosphonic acids, KuQ-phosphonate esters hydrolysis was performed [53].…”

Section: Resultsmentioning

confidence: 95%

“…With respect to photoelectrochemical applications, we have been recently involved in the use of metal-free quinoid compounds, i.e., KuQuinones (KuQs), as photosentisiz-ers on indium-tin oxide (ITO) [28], NiO [29] and on SnO 2 [30], due to their favorable electrochemical and photophysical properties [31]. In this respect, terminal hydroxy or carboxylic acid functionalities were introduced in KuQuinone structure to ensure a stable and effective metal oxide binding.…”

Section: Introductionmentioning

confidence: 99%

A Sustainable Improvement of ω-Bromoalkylphosphonates Synthesis to Access Novel KuQuinones

et al. 2021

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Owing to the attractiveness of organic phosphonic acids and esters in the pharmacological field and in the functionalization of conductive metal-oxides, the research of effective synthetic protocols is pivotal. Among the others, ω-bromoalkylphosphonates are gaining particular attention because they are useful building blocks for the tailored functionalization of complex organic molecules. Hence, in this work, the optimization of Michaelis–Arbuzov reaction conditions for ω-bromoalkylphosphonates has been performed, to improve process sustainability while maintaining good yields. Synthesized ω-bromoalkylphosphonates have been successfully adopted for the synthesis of new KuQuinone phosphonate esters and, by hydrolysis, phosphonic acid KuQuinone derivatives have been obtained for the first time. Considering the high affinity with metal-oxides, KuQuinones bearing phosphonic acid terminal groups are promising candidates for biomedical and photo(electro)chemical applications.

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Photoanodes for water oxidation with visible light based on a pentacyclic quinoid organic dye enabling proton-coupled electron transfer

Abstract: A novel pentacyclic quinoid photosensitizer with extended absorption in the visible region and enabling proton-coupled electron transfer is employed in photoelectrodes for water oxidation in combination with a ruthenium polyoxometalate catalyst.

Cited by 22 publications

References 40 publications

Molecular and heterogeneous water oxidation catalysts: recent progress and joint perspectives

Molecular and heterogeneous water oxidation catalysts: recent progress and joint perspectives

Unveiling KuQuinone Redox Species: An Electrochemical and Computational Cross Study

A Sustainable Improvement of ω-Bromoalkylphosphonates Synthesis to Access Novel KuQuinones

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