Electrochemical hydrogenation of perylene: dihydro- and tetrahydro-perylene

Rampazzo, Liliana; Zeppa, A.

doi:10.1016/s0022-0728(79)80353-8

Cited by 7 publications

(6 citation statements)

References 18 publications

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“…2) exhibited four new bands at 352, 334, 319, and 305 nm. These bands are similar to those reported in the literature for H2PE (see Table I) (20), however, the wavelength maxima are red-shifted by approximately 8 nm. These results suggest that the dianion of PE (PE 2-) is being formed, and that it is complexed to a Lewis acid resulting in a UV/visible spectrum similar to that of H2PE.…”

Section: Perylene In Basic Aici3-emic (444 M/o Aici~)--pe Wassupporting

confidence: 89%

“…dissolved in the basic A1C13-EMIC mixture at a concentration of 4.63 mM to give a yellow solution with blue fluorescence. The UV/visible spectrum was similar to that reported in the literature for PE in other solvents (Table I) (19,20). Cyclic voltammetry at a tungsten electrode (Fig.…”

Section: Perylene In Basic Aici3-emic (444 M/o Aici~)--pe Wassupporting

confidence: 81%

“…340 mV) was considerably less than that reported in the literature for the two step reduction of PE in aprotic solvents (approx. 550 mV) (20). This type of shift has been reported for the reduction of aromatic compounds in the presence of a protic source (21).…”

Section: Perylene In Basic Aici3-emic (444 M/o Aici~)--pe Wassupporting

confidence: 73%

“…Electrochemical and spectroscopic data suggest that the reduction of PE in basic A1C13-EMIC proceeds via two successive reduction/complexation steps (ECEC) with the radical anion being the product of the first reduction step. When reduced in the presence of a protic source, PE has been shown to form H2PE via an ECEC mechanism (20,(29)(30)(31). However, the low concentration of protic impurities cannot account for the observed results.…”

Section: Perylene In Basic Aici3-emic (444 M/o Aici~)--pe Wasmentioning

confidence: 92%

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Reduction of Aromatic Compounds in Organic Chloroaluminate Melts: II . Perylene

Coffield

Mamantov

Zingg

et al. 1992

J. Electrochem. Soc.

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The electroreduction of perylene in basic mixtures of AiCI~ and 1-ethyl-3-methyl-lH-imidazolium chloride (44.4 mol % A1C13) as well as 1,2-dimethyl-3-propyl-lH-imidazolium chloride (47.4 mol % A1C13) has been investigated by electrochemical, spectroscopic, and spectroelectrochemical techniques. The reduction of perylene proceeds through an ECEC process with the likely product being the aluminum chloride adduct of the dianion of perylene. In addition, a radical anion intermediate has been identified and its rate of decay measured.

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Section: Perylene In Basic Aici3-emic (444 M/o Aici~)--pe Wassupporting

confidence: 89%

Section: Perylene In Basic Aici3-emic (444 M/o Aici~)--pe Wassupporting

confidence: 81%

Section: Perylene In Basic Aici3-emic (444 M/o Aici~)--pe Wassupporting

confidence: 73%

Section: Perylene In Basic Aici3-emic (444 M/o Aici~)--pe Wasmentioning

confidence: 92%

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Reduction of Aromatic Compounds in Organic Chloroaluminate Melts: II . Perylene

Coffield

Mamantov

Zingg

et al. 1992

J. Electrochem. Soc.

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“…A more significant secondary product under MW or prolonged reflux conditions was assigned as 2,3-dihydroperylene ( 15 ). This has been reported previously as a product of electrochemical reduction of 11 . The same product could be produced in ca.…”

Section: Resultsmentioning

confidence: 99%

Scholl Cyclizations of Aryl Naphthalenes: Rearrangement Precedes Cyclization

et al. 2015

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In 1910, Scholl, Seer, and Weitzenbock reported the AlCl3-catalyzed cyclization of 1,1'-binaphthyl to perylene. We provide evidence that this classic organic name reaction proceeds through sequential and reversible formation of 1,2'- and 2,2'-binaphthyl isomers. Acid-catalyzed isomerization of 1,1'-binaphthyl to 2,2'-binaphthyl has been noted previously. The superacid trifluoromethanesulfonic acid (TfOH), 1 M in dichloroethane, catalyzes these rearrangements, with slower cyclization to perylene. Minor cyclization products are benzo[k]fluoranthene and benzo[j]fluoranthene. At ambient temperature, the observed equilibrium ratio of 1,1'-binaphthyl, 1,2'-binaphthyl, and 2,2'-binaphthyl is <1:3:97. DFT calculations with the inclusion of solvation support a mechanistic scheme in which ipso-arenium ions are responsible for rearrangements; however, we cannot distinguish between arenium ion and radical cation mechanisms for the cyclization steps. Under similar reaction conditions, 1-phenylnaphthalene interconverts with 2-phenylnaphthalene, with the latter favored at equilibrium (5:95 ratio), and also converts slowly to fluoranthene. Computations again support an arenium ion mechanism for rearrangements.

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Molecular Catalysis of Electrochemical Reactions: Competition between Reduction of the Substrate and Deactivation of the Catalyst by a Cosubstrate Application to N₂O Reduction

2021

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In the context of molecular catalysis of electrochemical reactions, the competition between reduction of the substrate and deactivation of the catalyst by a cosubstrate is investigated. It is a frequent situation because proton donors are ubiquitous cosubstrates in reductive electrochemical reactions and molecular catalysts, either transition metal complexes or organic aromatic molecules, and are often prone to electrohydrogenation. We provide a formal kinetic analysis in the framework of cyclic voltammetry, and we show that the response is governed by two parameters and that the competition does not depend on the scan rate. From this analysis a methodology is proposed to analyze such systems and then illustrated via the study of N2O to N2 electroreduction catalyzed by 4‐cyanopyridine in acetonitrile electrolyte with water as proton donor. Incidentally, new insights into the mechanism of 4‐cyanopyridine radical anion protonation are revealed.

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Electrochemical hydrogenation of perylene: dihydro- and tetrahydro-perylene

Cited by 7 publications

References 18 publications

Reduction of Aromatic Compounds in Organic Chloroaluminate Melts: II . Perylene

Reduction of Aromatic Compounds in Organic Chloroaluminate Melts: II . Perylene

Scholl Cyclizations of Aryl Naphthalenes: Rearrangement Precedes Cyclization

Molecular Catalysis of Electrochemical Reactions: Competition between Reduction of the Substrate and Deactivation of the Catalyst by a Cosubstrate Application to N₂O Reduction

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Electrochemical hydrogenation of perylene: dihydro- and tetrahydro-perylene

Cited by 7 publications

References 18 publications

Reduction of Aromatic Compounds in Organic Chloroaluminate Melts: II . Perylene

Reduction of Aromatic Compounds in Organic Chloroaluminate Melts: II . Perylene

Scholl Cyclizations of Aryl Naphthalenes: Rearrangement Precedes Cyclization

Molecular Catalysis of Electrochemical Reactions: Competition between Reduction of the Substrate and Deactivation of the Catalyst by a Cosubstrate Application to N2O Reduction

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Molecular Catalysis of Electrochemical Reactions: Competition between Reduction of the Substrate and Deactivation of the Catalyst by a Cosubstrate Application to N₂O Reduction