Cathodic t-Butylation of Pyrene.

Hansen, Poul Erik; Berg, Albert van den; Lund, Hakon; Devreux, Michel; Vialle, J.P.; Anthonsen, T.

doi:10.3891/acta.chem.scand.30b-0267

Cited by 22 publications

(11 citation statements)

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“…Surprisingly, this route has only been sparingly explored. Thus, tert-butylation 28 and isopropylation 29 have been performed by electrochemical reduction of pyrene in the presence of the corresponding alkyl chlorides. However, yields were rather modest especially for isopropyl-substituted pyrene because numerous isomers and dehydrogenated compounds were produced.…”

Section: Introductionmentioning

confidence: 99%

Towards sustainable synthesis of pyren-1-yl azoliums via electrochemical oxidative C–N coupling

et al. 2015

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Electrosynthesis of 1-methyl-3-(pyren-1-yl)-1H-imidazol-3-ium tetrafluoroborate via oxidative C-N coupling of pyrene with methylimidazole is optimized with the aim to reduce waste and simplify the experimental setup. Several parameters are tested such as cell configuration (number of compartments), pyrene concentration, amount of nucleophile, electrosynthetic method (potentiostatic/galvanostatic), 10 amount of electrons, atmosphere (Ar/air), solvent quality and presence/absence of supporting electrolyte. The optimized conditions are successfully applied to the synthesis of 1-methyl-3-(pyren-1-yl)-1Hbenzimidazol-3-ium tetrafluoroborate, 1-methyl-4-(pyren-1-yl)-1H-1,2,4-triazol-4-ium tetrafluoroborate and 3-(pyren-1-yl)-benzothiazol-3-ium tetrafluoroborate. These four pyren-1yl-azolium salts are characterized by NMR, MS, elemental analysis, UV-Vis. absorption and emission spectroscopies. The X-15 ray crystallographic structures of 1-methyl-3-(pyren-1-yl)-1H-imidazol-3-ium tetrafluoroborate and 1methyl-3-(pyren-1-yl)-1H-benzimidazol-3-ium tetrafluoroborate are presented.

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Section: Introductionmentioning

confidence: 99%

Towards sustainable synthesis of pyren-1-yl azoliums via electrochemical oxidative C–N coupling

et al. 2015

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“…However, the introduction of alkyl groups, which are the most ubiquitous substituents, to pyrene at the 1-, 3-, 6-, and 8-positions has not been performed in a systematic way. Therefore, how alkyl groups affect the PL properties of pyrene has not been discussed in detail, although alkylpyrene derivatives are often prepared and some have been studied individually. ,− Thus, in the field of organic material science in general, the introduction of alkyl groups was mostly carried out not to tune photophysical properties but to enhance the solubility and suppress π–π stacking. ,− In other words, it is often believed that alkyl groups do not significantly affect the PL properties of chromophores. On the other hand, it has been reported that in oligo- p -phenylene dyes and polycyclic aromatic hydrocarbon dyes such as naphthalene and anthracene, the introduction of a methyl group at an appropriate position sometimes changes the chromophore’s properties such as its fluorescence quantum yield and lasing properties .…”

Section: Introductionmentioning

confidence: 99%

Fluorescence Enhancement of Pyrene Chromophores Induced by Alkyl Groups through σ–π Conjugation: Systematic Synthesis of Primary, Secondary, and Tertiary Alkylated Pyrenes at the 1, 3, 6, and 8 Positions and Their Photophysical Properties

et al. 2013

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We have systematically synthesized 1-, 3-, 6-, and 8-alkyl-substituted pyrene derivatives using the latest synthesis methods and investigated the effects of alkyl substitution on the photophysical properties of the pyrene chromophore. Like the trimethylsilyl group, which is known to enhance the fluorescence properties of some chromophores through σ*-π* conjugation, alkyl groups (primary, secondary, and tertiary) enhanced the fluorescence quantum yield of the pyrene chromophore through σ-π conjugation in most cases. While these enhancements in the fluorescence quantum yield were beyond expectations, the results were supported by absolute measurements. These results also indicate that ubiquitous alkyl groups can be used to tune the photophysical properties of the pyrene chromophore, as well as to improve the solubility or prevent aggregation. In other words, they can be used to develop new photofunctional materials.

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“…For the study of mass spectra of alkyltetrahydronaphthalenes in geological samples, a series of methyl and dimethyltetrahydronaphthalenes was prepared, in analogy with cathodic butylation of naphthalene and pyrene (Simonet, Michel & Lund, 1975;and Hansen, Berg & Lund, 1976). A large series of tetrathydronaphthalenes as reported from the Green River Shale by Anders, Doolittle & Robinson (1973) is present in both samples.…”

Section: Results and Discussion•mentioning

confidence: 99%

Organic compounds from Cretaceous coals of Nûgssuaq, West Greenland

Lam¹,

Pedersen²

1978

bullggu

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Bituminous coals from the Lower Cretaceous Korne Formation and the Upper Cretaceous Atane Formation of Nûgssuaq have been analyzed for organic compounds. In the Atane Formation n-C12- to n-C31-alkanes, C19- and C20-isoprenoids (pristane and phytane) and possibly C14-, C15-, and C16-isoprenoids are present. n-C9- to n-C28-acids, norphytanic acid and phytanic acid have also been detected. In the Korne Formation n-C14- to n-C27-alkanes, C19- and Czoisoprenoids and possibly C14- and C15-isoprenoids are present. n-C8- to n-C26 -acids, in addition C8- to C20-α, ω-diacids could be detected. The difference between the Korne flora (predominantly gymnosperms and ferns) and the Atane flora (dominated by angiosperms) is not apparent in the organic chemistry. Comparisons are made with extracts from Rhaetic-Liassic coal from the Kap Stewart Formation of East Greenland where only C14- and C16-acids and aromatic acids were detected.

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Cathodic t-Butylation of Pyrene.

Cited by 22 publications

References 0 publications

Towards sustainable synthesis of pyren-1-yl azoliums via electrochemical oxidative C–N coupling

Towards sustainable synthesis of pyren-1-yl azoliums via electrochemical oxidative C–N coupling

Fluorescence Enhancement of Pyrene Chromophores Induced by Alkyl Groups through σ–π Conjugation: Systematic Synthesis of Primary, Secondary, and Tertiary Alkylated Pyrenes at the 1, 3, 6, and 8 Positions and Their Photophysical Properties

Organic compounds from Cretaceous coals of Nûgssuaq, West Greenland

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