The Effect of Reduction Potential on the Generation 
of the Perylene Diimide Radical Anions

Zhao, Yuzhen; Li, K. X.; Ding, Siyi; Zhu, Min; Ren, Huaping; Ma, Qiang; Guo, Zhun; Tian, Shichao; Zhang, H. Q.; Miao, Zongcheng

doi:10.1134/s003602441807035x

Cited by 5 publications

(8 citation statements)

References 23 publications

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“…In particular, our PDI shows a redox potential value ( E 1/2 (PDI . − /PDI) vs. Fc/Fc + =−0.95 V (−0.57 V vs. saturated calomel electrode, SCE)) in agreement with those reported for related perylenes . Upon excitation, both the reductive and oxidative properties of PDI are enhanced and therefore, the PDI excited state (PDI*) can experience an electron transfer process with common electron donors, such as amines, forming a PDI radical anion (PDI .…”

Section: Resultssupporting

confidence: 84%

“…In particular, our PDI shows ar edox potential value (E 1/2 (PDIC À /PDI) vs. Fc/Fc + = À0.95 V( À0.57 Vv s. saturated calomel electrode, SCE)) in agreement with those reported for related perylenes. [22] Upon excitation,b oth the reductive and oxidative properties of PDI are enhanced [1d] and therefore, the PDI excited state (PDI*) can experience an electron transfer process with common electron donors, such as amines,f orming aP DI radicala nion( PDIC À , E 1/2 (PDIC À /PDI*)v s. SCE =+1.77 V). The presenceo ft his speciesi se asily detected by UV/Vis spectroscopy owing to the characteristica bsorption band of PDIC À around 700 nm.…”

Section: Sensitizedsinglet Oxygen Formationmentioning

confidence: 99%

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Perylene‐Grafted Silicas: Mechanistic Study and Applications in Heterogeneous Photoredox Catalysis

Carrillo

Elhage

Marín

et al. 2019

Chemistry A European J

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A mechanistic study is herein presented for the use of heterogeneous photocatalysts based on perylene moieties. First, the successful immobilization of perylene diimides (PDI) on silica matrices is demonstrated, including their full characterization by means of electronic microscopy, surface area measurements, powder XRD, thermogravimetric analysis, and FTIR, 29Si and 13C solid‐state NMR, fluorescence, and diffuse reflectance spectroscopies. Then, the photoredox activity of the material was tested by using two model reactions, alkene oxidation and 4‐nitrobenzylbromide reduction, and mechanistic studies were performed. The mechanistic insights into their photoredox activity show they have promising dual photocatalytic activity for both organic oxidations and reductions.

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Section: Resultssupporting

confidence: 84%

Section: Sensitizedsinglet Oxygen Formationmentioning

confidence: 99%

Perylene‐Grafted Silicas: Mechanistic Study and Applications in Heterogeneous Photoredox Catalysis

Carrillo

Elhage

Marín

et al. 2019

Chemistry A European J

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“…The proposed basis of the photocatalytic activity comes from the formation of the PBI radical anion (PBI •-) and dianion (PBI 2-) via photoreduction. 50,51 We find that using electrochemistry (Section 4.7 in the Supporting Information) that PBI-A has driving force for H2 evolution at pH 6.0 and below from PBI •and 7.0 and below from PBI 2-.Similarly, PBI-Y and others have driving force for H2 production below pH 6.0-7.0. Therefore, the onset for H2 evolution (and relative yield) is not solely due to reduction potential.…”

Section: Resultsmentioning

confidence: 89%

Controlling Activity by Self-Assembly – Tuning Perylene Bisimide Photocatalysts for the Hydrogen Evolution Reaction

McDowall¹,

Greeves²,

McAulay³

et al. 2020

Preprint

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Amino acid functionalised perylene bisimides (PBIs) form self-assembled structures in solution, the nature of which depends on the local environment. Using a high throughput photocatalysis set-up, we have studied five PBIs for the hydrogen evolution reaction (HER) under a range of conditions (pH and hole scavenger concentration) across 350 experiments to explore the relationship between supramolecular structure and photocatalytic activity. Using small angle X-ray scattering (SAXS), we show that photocatalytic activity is determined by the nature of the self-assembled aggregate that is formed with a correlation between the presence of charged flexible cylindrical aggregates and high levels of H2. Our work highlights the complexity of designing supramolecular photocatalysts, and also the power of tuning activity by the type of aggregate that is formed.

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“…This indicates that the pH dependence alone is not due to the driving force for charge transfer from the singly (PBI ○− ) and doubly reduced (PBI 2− ) species. [ 42,43 ]…”

Section: Resultsmentioning

confidence: 99%

“…This indicates that the pH dependence alone is not due to the driving force for charge transfer from the singly (PBI ○− ) and doubly reduced (PBI 2− ) species. [42,43] In addition to acting as an electron scavenger, methanol can change the solubility of PBI and its differing properties as a solvent can affect both the structure of the aggregates and the photophysics of the material. To explore the possible wider role of methanol concentration on photocatalytic activity and structure, we have expanded our study to use six methanol concentrations (0 Regardless of the methanol concentration used, we find that both PBI-A shows the maximum level of photocatalytic H 2 evolution from pH 4.0 to 5.0, in agreement with the initial screen of PBIs and pH ( Figure 4).…”

Section: (4 Of 10)mentioning

confidence: 99%

Controlling Photocatalytic Activity by Self‐Assembly – Tuning Perylene Bisimide Photocatalysts for the Hydrogen Evolution Reaction

McDowall

Greeves

Clowes

et al. 2020

Advanced Energy Materials

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usually strongly absorbing in the visible light region and many possess n-type semiconductor behavior when aggregated. [8,9] PBIs often self-assemble in solution at high concentrations or when given a suitable trigger. They typically self-assemble into 1D structures such as nanofibers or nanotubes, a process driven by non-covalent interactions such as hydrogen bonding, van der Waals interactions, and π-π stacking. [2,3,10-14] The electronic properties of PBIs can be tuned by how they are functionalized and by the type of self-assembled aggregate that is formed. [10,15] Using solar energy to generate H 2 and O 2 from water is highly desirable to form part of a "green economy". [16-18] H 2 can be used as a fuel for combustion, within fuel cells and both H 2 and O 2 are also important chemical feedstocks. [17,18] PBIs and the related perylene monoimides (PMIs) have shown promise in the utilization of solar energy to drive chemical reactions, and have been shown to be able to act as effective photocatalysts for both H 2 evolution and O 2 evolution reactions. [19-23] Some of these systems use perylene mono or bis imides in a self-assembled state, but other self-assembled photocatalysts

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The Effect of Reduction Potential on the Generation of the Perylene Diimide Radical Anions

Cited by 5 publications

References 23 publications

Perylene‐Grafted Silicas: Mechanistic Study and Applications in Heterogeneous Photoredox Catalysis

Perylene‐Grafted Silicas: Mechanistic Study and Applications in Heterogeneous Photoredox Catalysis

Controlling Activity by Self-Assembly – Tuning Perylene Bisimide Photocatalysts for the Hydrogen Evolution Reaction

Controlling Photocatalytic Activity by Self‐Assembly – Tuning Perylene Bisimide Photocatalysts for the Hydrogen Evolution Reaction

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