ChemInform Abstract: ELEKTROCHEMISCHE OXIDATION VON 2,3,4,5‐TETRAPHENYL‐FURAN IN NITROMETHAN

Libert, Michel; Caullet, Claude

doi:10.1002/chin.197436071

Cited by 2 publications

(8 citation statements)

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“…[1] [note that the same spectrophotofluorometer and photomultiplier tube were employed in this study and the prevfous one (7)] Eex -~ 1.27Epa + 1.60 [1] The Epa of TPP of 0.90V vs. SCE yields an Eex of 2.73 eV (.equivalent to emission at 450 nm) with this equation, which is very close to the experimentally observed value. The observed emission consists of a band at 400 nm, where TPP fluoresces, and a longer wavelength band at 445 nm.…”

Section: Nap(--)/tpp(+)--the Reaction Enthalpy For Thesupporting

confidence: 77%

“…Recently such work has been published by Sundholm (4) and Iwakura et al (5); the residual water content was rather high (120 ppm) in the work of Iwakura, and also appreciable in the experiments reported by Sundholm. The electrooxidation of methanol in aqueous solutions has been extensively investigated since this material can be a very attractive fuel in a methanolair fuel cell (1-3).…”

Section: Introductionmentioning

confidence: 77%

“…The preparation and purification of the pyrrole, furan, and thiophene compounds has been described (1)(2)(3)(4)(5)(6). Tri-p-tolylamine (TPTA), naphthalene (NAP), benzophenone (BP), 2,5-diphenyl-1,3,4-oxadiazole (PPD), acetonitrile (ACN), and tetra-n-butylammonium perchlorate (TPAP) were obtained and treated as previously reported (7,8).…”

Section: Methodsmentioning

confidence: 99%

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Electrogenerated Chemiluminescence: XXVI . Systems Involving Tetraarylpyrroles, Tetraphenylfuran, and Tetraphenylthiophene

Libert

Bard²

1976

J. Electrochem. Soc.

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The production of light upon the electron transfer reaction of electrogenerated radical ions of tetraarylpyrroles [aryl = anisyl (TAP), phenyl (TPP), tolyl (TTP), p-chloro-phenyl (TCPP)], tetraphenylfuran (TPF), and tetraphenylthiophene (TPT) in systems containing these compounds alone in acetonitrile solutions or in mixed systems containing naphthalene, 2,5-diphenyl-l,3,4-oxadiazole, benzophenone, and tri-p-tolylamine is reported. Emission which corresponds to the fluorescence of the TAP, TPP, TTP, TPF, and TPT, as well as longer wavelength emission attributed to exciplex emission for some mixed systems, is observed. The singlet and triplet level energies of the compounds of interest are estimated and their cyclic voltammetric behavior described briefly.The usual basic requirements for a system which produces light upon the electron transfer reaction of + electrogenerated species, e.g., A-and D" (electrogenerated chemiluminescence or ECL), include the formation of stable radical ions, the fluorescence of at least one of the parent species (A and D), and sufficient free energy release in the A-/D*" reaction to form an M excited state. Moreover, efficient ECL systems, such as those involving 9,10-diphenylanthracene and rubrene, involve bulky molecules in which steric effects appear to hinder formation of complexes between the reactant species. Previous studies (1-6) have shown that tetra-aryl substituted five-member ring compounds (pyrroles, furans, and thiophenes) X = NH Ar~Ar

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Section: Nap(--)/tpp(+)--the Reaction Enthalpy For Thesupporting

confidence: 77%

Section: Introductionmentioning

confidence: 77%

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Electrogenerated Chemiluminescence: XXVI . Systems Involving Tetraarylpyrroles, Tetraphenylfuran, and Tetraphenylthiophene

Libert

Bard²

1976

J. Electrochem. Soc.

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“…This fact could explain the generation of relatively high yields (32-75%) of 4 from substrates IV-VI, when electrolysis was conducted under air atmosphere (Table 2). It is noteworthy that, in comparison with other fivemembered heterocycles, for instance, the anodic oxidation of tetraphenylfuran produced dibenzoylstilbene (1) in 90% yield [32]; under different conditions, 2,5-dihydroxylation derivatives were formed [30]. Electrolysis of tetraphenylthiophene also afforded 1 in a 40% yield [29].…”

Section: Discussion and Mechanismmentioning

confidence: 95%

“…The latter could accept an electron from e.g., the parent silacyclopentadiene to afford endoperoxide D, from which products 1 and 9 are generated after rearrangement. It is noteworthy that this type of rearrangement is known [29,30] when singlet oxygen reacts with 1,1-dimethyl-2,3,4,5-tetraphenyl-1-silacyclopentadiene, as described in Scheme 4. However, irradiation of 1-methyl-vinyl-2,3,4,5-tetraphenyl-1-silacyclo-pentadiene under a stream of air gave a mixture of oxygenated products, including 1 and its dihydro derivative, but no product containing a silicon atom was detected [5].…”

Section: Discussion and Mechanismmentioning

confidence: 98%