One-pot Synthesis of 1,2,3,4-Tetrafluoroacridines from pentafluorobenzaldehyde1

Adamson, A. J.; Banks, R. E.; Fields, R.; Tipping, A. E.

doi:10.1039/a607642d

Cited by 6 publications

(11 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Following the synthetic procedure reported in the literature, , we have synthesized the 1,2,3,4-tetrafluoro-7-methoxyacridine ( 6 ) and the 1,2,3,4-tetrafluoro-9-methoxyacridine ( 7 ), by reacting 2-methoxy or 4-methoxyaniline with pentafluorobenzaldehyde in refluxing xylene. As expected the reactivity of the amino function is sterically hindered by the presence of the methoxy group in the ortho position and the final acridine ( 7 ) has been collected in a lower yield than 6 (see Table ).…”

Section: Resultssupporting

confidence: 68%

Synthesis and Properties of Polyfluorohydroxyacridines and Their Zn²⁺ Complexes: New Materials for Solid State Emitting Systems

et al. 2004

View full text Add to dashboard Cite

1,2,3,4-tetrafluoroacridines are easily accessible by refluxing electron-rich aromatic amines with pentafluorobenzaldehyde. This procedure, however, fails when 4-hydroxyaniline is employed for the preparation of the corresponding tetrafluorohydroxyacridine. The synthesis of this substrate, here described, has been accomplished by an indirect methodology: the synthesis of the corresponding tetrafluoromethoxyacridine was followed by the ether function cleavage by refluxing them in 47% aqueous HBr. In the case of 1,2,3,4-tetrafluoro-9-methoxyacridine a peculiar reactivity has been observed, indeed the substitution of a fluorine by a bromine atom occurs contemporaneously with the ether hydrolysis. The position of bromine on acridine moiety has been ascertained by X-ray analysis on a single crystal of this compound. The fluorine substitution did not occur when the hydrolysis was carried out employing the ionic liquid triethylammonium eptachloro alluminate. The synthesized polifluorohydroxyacridines have been fully optically and spectroscopically characterized. 1,2,3,4-Tetrafluoro-9-hydroxyacridine and 2-bromo-1,3,4-trifluoro-9-hydroxyacridine were employed to prepare complexes with Zn2+. These complexes were optically characterized by optical absorption and photoluminescence both in solution and in the solid state, and a preliminary discussion about the photophysics of these complexes is presented.

show abstract

Section: Resultssupporting

confidence: 68%

Synthesis and Properties of Polyfluorohydroxyacridines and Their Zn²⁺ Complexes: New Materials for Solid State Emitting Systems

et al. 2004

View full text Add to dashboard Cite

show abstract

“…The molecular structure of e is reported in Figure , and Table lists selected bond distances and angles . The molecular and solid-state structure of e is strictly related to those observed for the other 1,2,3,4-tetrafluoroacridines characterized in the solid state by X-ray diffraction analysis, namely the 7-methoxy 12c (compound c ) and 7-fluoro derivatives 12c. In particular, comparison of the bonding features of c and e shows a close similarity between the acridinic unit, with partial localization of double bonds (C(1)−C(2), C(3)−C(4), C(8)−C(9) and C(10)−C(11) for e , see Table ).…”

Section: Resultsmentioning

confidence: 55%

“…The flexibility and the feasibility of this synthesis, together with the availability of a large number of different anilines, open the possibility of preparing a large pool of these substrates. First, we have repeated some of the synthesis of tetrafluoroacridine in refluxing toluene, as described in the literature, obtaining similar results. However, the use of refluxing xylene (bp 138−140 °C) as solvent and increasing the amount of aniline to 3 equiv allowed us to improve the yields.…”

Section: Resultsmentioning

confidence: 87%

“…Later on, fluoroacridines were produced by heating fluorinated acetophenones with aniline . The most interesting way to prepare fluoroacridines was reported by Banks et al in the early 1990s when the synthesis of these substrates was performed by reacting the pentafluorobenzaldehyde with p - anisidine . Banks also investigated the mechanism of this reaction.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and Properties of Some Derivatives of 1,2,3,4-Tetrafluoroacridine for Solid State Emitting Systems

et al. 2003

View full text Add to dashboard Cite

The resonant energy transfer (RET) between fluorescent organic molecules is a very important phenomenon widely investigated for its potential in developing devices such as light-emitting diodes and lasers. Energy transfer processes take place between two different molecules and they are usually observed when the emission spectrum of the first molecule (called donor) overlaps with the absorption spectrum of the other one (called acceptor). The individuation of this kind of molecule inside a common structural motif represents an interesting approach aimed at simplifying the modeling of their synthetic procedure; indeed the desired couple can be obtained simply acting on the electronic properties of substituents present on the molecule and helps the understanding of the energy transfer processes. The tetrafluoroacridines, readily accessible from aniline and pentafluorobenzaldehyde, have been selected as a structural motif because their absorption and emission properties can be easily tuned by acting on the nature of substituents present on the starting aniline. The synthesis of new terms of these molecules along with a preliminary study on their optical, electrochemical, and structural properties, in solution and in the solid state, is described. We present here a study on the optical properties of a molecular crystal of donor doped with molecules of acceptor, both chosen among the prepared tetrafluoroacridines; the temperature dependence of luminescence spectrum allowed us to take a glance upon the energy transfer and excitation migration phenomena occurring in this system.

show abstract

“…This condensation products undergo S N Ar reactions of ortho-and para-fluorine in the presence of excess arylamine (Scheme 76 [611][612][613][614][615][616][617]). The ratio of two forming product (85, 86a-g) changes depended on the substituents and on amount aniline utilized.…”

Section: Cyclization Reactions Of Pentafluorobenzaldehyde Utilizing Tmentioning

confidence: 99%

Pentafluorobenzaldehyde and its utilizing in organic synthesis

Pažitný

Solčan

Végh

2009

Journal of Fluorine Chemistry

View full text Add to dashboard Cite

One-pot Synthesis of 1,2,3,4-Tetrafluoroacridines from pentafluorobenzaldehyde1

Cited by 6 publications

References 6 publications

Synthesis and Properties of Polyfluorohydroxyacridines and Their Zn²⁺ Complexes: New Materials for Solid State Emitting Systems

Synthesis and Properties of Polyfluorohydroxyacridines and Their Zn²⁺ Complexes: New Materials for Solid State Emitting Systems

Synthesis and Properties of Some Derivatives of 1,2,3,4-Tetrafluoroacridine for Solid State Emitting Systems

Pentafluorobenzaldehyde and its utilizing in organic synthesis

Contact Info

Product

Resources

About

One-pot Synthesis of 1,2,3,4-Tetrafluoroacridines from pentafluorobenzaldehyde1

Cited by 6 publications

References 6 publications

Synthesis and Properties of Polyfluorohydroxyacridines and Their Zn2+ Complexes: New Materials for Solid State Emitting Systems

Synthesis and Properties of Polyfluorohydroxyacridines and Their Zn2+ Complexes: New Materials for Solid State Emitting Systems

Synthesis and Properties of Some Derivatives of 1,2,3,4-Tetrafluoroacridine for Solid State Emitting Systems

Pentafluorobenzaldehyde and its utilizing in organic synthesis

Contact Info

Product

Resources

About

Synthesis and Properties of Polyfluorohydroxyacridines and Their Zn²⁺ Complexes: New Materials for Solid State Emitting Systems

Synthesis and Properties of Polyfluorohydroxyacridines and Their Zn²⁺ Complexes: New Materials for Solid State Emitting Systems