ChemInform Abstract: RK. AROMATISCHER POLYFLUORKETONE MIT ANILIN

Vasilevskaya, T. N.; Baturina, I. I.; Kollegova, M. I.; Gerasimova, T. N.; Barkhash, V. A.

doi:10.1002/chin.197141336

Cited by 4 publications

(3 citation statements)

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“…1,2,3,4-tetrafluoroacridine was synthesized for the first time in the late 1960s, through a multistep reaction from bromobenzene involving a modified Lehmsted−Tananescu rearrangement, with the aim of studying the effect of fluorination on the pharmacological effects of some acridine derivatives. 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 .…”

Section: Resultsmentioning

confidence: 99%

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

et al. 2003

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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.

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Section: Resultsmentioning

confidence: 99%

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

et al. 2003

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“…2 Since this route involved both 1,2,3,4-tetrafluoro-9(10H)-acridone and 9-chloro-1,2,3,4-tetrafluoroacridine as intermediates, it possessed potential as a source of several other derivatives of 1,2,3,4-tetrafluoroacridine; however, this opportunity seems not to have been pursued, although the development of other routes to 1,2,3,4-tetrafluoro-9(10H)-acridone (electrochemical oxidation of 2-amino-3,4,5,6-tetrafluorobenzophenone; KF-driven cyclization of 2-amino-2,3,4,5,6-pentafluorobenzophenone) was undertaken, and this led to the synthesis of octafluoro-9(10H)-acridone. 3,4 Of more relevance to the work described in detail 1 here are reports concerning fluorinated acridones from Russian researchers in the 1970s, notably that (i) thermal treatment of methyl pentafluorophenyl ketone with aniline affords, inter alia, 3-anilino-1,2,4-trifluoro-9-methylacridine 5 (a reaction extended later to derivatives of aniline 6 ) and (ii) the preparation of 1,2,3,4-tetrafluoroacridine (1a) from pentafluorobenzaldehyde and the Grignard reagent PhNHMgBr. 7 The work reported here stemmed from a serenedipitous discovery, made during mass spectrometric studies on fluorinated Schiff bases, 8,9 that condensation of pentafluorobenzaldehyde with p-anisidine under forcing conditions yields 4-methoxy-N-(pentafluorobenzylidene)aniline (4b) contaminated with, inter alia, a product of molecular formula C 14 H 7 F 4 NO.…”

mentioning

confidence: 95%

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

Adamson¹,

Banks²,

Fields³

et al. 1997

J. Chem. Res.

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“…107 The formation of 9 methyl 3 phenylamino or 3 phenyl amino 9 trifluoromethylacridine on heating of penta fluoroacetophenone 234 or perfluoroacetophenone with aniline was reported in Ref. 108.…”

Section: Scheme 70mentioning

confidence: 96%