Photo-induced Friedel-Crafts acylation of anthracene with aroyl chlorides.

doi:10.1246/BCSJ.51.1145

Paper

Photo-induced Friedel-Crafts acylation of anthracene with aroyl chlorides.

Published Apr 1, 1978 · T. Tamaki

Bulletin of the Chemical Society of Japan

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Abstract

The photo-excitation of anthracene (1) in the presence of benzoyl chloride and its p- or m-substituted compounds (2) gave the corresponding 2- and 9-aroylanthracenes. No isomeric 1-aroylanthracenes (3) were detected. The aroyl chlorides (2) were found to quench the fluorescence of 1. The quenching constants obtained increased with increasing electron-withdrawing ability of the substituents and are in agreement with those independently obtained from the quantum yield determinations. The efficiency of the photoaroylation was dependent on the solvent polarity. The results suggest a plausible photochemical mechanism, which involves a CT complex formed from 1 in the excited singlet state and 2 in the ground state. This complex formation is supported by the positional selectivity exhibited in the product distribution.

Study Snapshot

Photo-induced Friedel-Crafts acylation of anthracene with aroyl chlorides produces 2- and 9-aroylanthracenes, with the efficiency depending on solvent polarity and electron-withdrawing ability of the substituents.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Photo-induced Friedel-Crafts acylation of anthracene with aroyl chlorides.

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References

Absorption and Emission Spectra of Anthracene Dimers

Anthracene dimers show different absorption and fluorescence spectra, revealing their geometry and resonance splittings in the 1B2u and 1B3u states.

Electronic Spectra of Acridine and Phenazine

The electronic spectra of acrylin and phenazine are generally consistent with observed excitation energies and oscillator strengths, with a detailed discussion of electronic transition mechanisms.

Photochemical ethoxycarbonylmethylation of benzene with ethyl haloacetate in the presence of metallic halides

Photochemical ethoxycarbonylmethylation of benzene with ethyl haloacetate in the presence of metallic halides produces ethyl phenylacetate as a sole photoproduct, with no detectable diethyl succinate.

Topochemistry. Part XXXIII. The Solid‐State Photochemistry of Some Anthracene Derivatives

Solid-state photochemistry of 9-substituted anthracenes yields centrosymmetric dianthracenes, with some monomers crystallizing in parallel-stack type with a 4 A axis, yielding non-topochemical head-to-tail dimers.

Citations

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Thioxanthone based one-component polymerizable visible light photoinitiator for free radical polymerization

TX-PA is an effective one-component polymerizable visible light photoinitiator with excellent migration stability, offering potential for use in food packaging and biomedical fields.

Fluorescence quenching of para‐substituted styrenes by tetramethylethylene. Correlation analysis of the quenching coefficient KSV and the quenching rate constant kq by the dual‐parameter equation with polar and spin‐delocalization substituent constants

There may be no need to use excited-state substituent constants for fluorescence quenching of excited states of styrenes, as the correlation between KSV and xx shows excellent results.

Phenanthrene-olefin exciplexes. Substituent effects

Substituted phenanthrenes exhibit fluorescent exciplexes in benzene, with linear correlations between fluorescence energies and quenching constants.

Triplet sensitization of anthracene photodimerization in γ-cyclodextrin

Anthracene photodimerization in -cyclodextrin can be successfully photosensitized using xanthene dyes, enabling host-assisted photoreaction.