Versuche zur polymerisation von fluoren

Prey, V.; Schindlbauer, H.; Cmelka, Dieter

doi:10.1002/apmc.1973.050280111

Cited by 11 publications

(7 citation statements)

References 8 publications

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“…15 As a result of this, polymerization is the dominating reaction in chloroform under the conditions of the experiments in agreement with previous reports that polymerization of 9H-fluorene occurs readily in solution in the presence of free AlCl 3 . 16,17 When acetylation was carried out in the non-polar carbon disulfide the conversion was moderate to high depending on the temperature and reaction time without notable formation of polymeric materials. In terms of the selectivity, 2-AcFl was the predominant isomer resulting from monoacetylation in most solvents except carbon disulfide, where also 2,7-DAcFl was detected in appreciable amounts (~5-13 %).…”

Section: Resultsmentioning

confidence: 99%

The synthesis of mono- and diacetyl-9H-fluorenes. Reactivity and selectivity in the Lewis acid catalyzed Friedel-Crafts acetylation of 9H-fluorene

Titinchi¹,

Kamounah²,

Abbo³

et al. 2008

Arkivoc

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Friedel-Crafts acetylation of 9H-fluorene is an effective route for the preparation of mono-and diacetyl-9H-fluorenes. Using acetylchloride as the reagent and aluminum chloride as the Lewis acid catalyst the effect of the solvent polarity, the temperature, the reaction time and the mode of addition (Perrier or Bouveault) on the reactivity-selectivity pattern was investigated. The results showed that monoacetylation of 9H-fluorene in chloroalkanes and nitromethane gives mixtures of 2-acetyl-and 4-acetyl-9H-fluorene with the former dominating. In addition to these two isomers, 2,7-diacetyl-9H-fluorene was obtained in 5-11 % yield when carbon disulfide was used as the solvent. Acetylation of 9H-fluorene in dichloroethane and carbon disulfide, using an excess of acetyl chloride and aluminum chloride at reflux temperature, gives 2,7-diacetyl-9H-fluorene exclusively in high yields (> 97%). Attempts to carry out diacetylation in nitromethane on the other hand resulted in the formation of monoacetyl derivatives only. The ketones obtained were isolated and identified by various physico-chemical techniques. The 1 H NMR spectrum of 4-acetyl-9H-fluorene is reported for the first time. Values of the total energies and the Gibbs free energies at 298K for 9H-fluorene, the five isomeric monoacetyl-9H-fluorenes and the four σ-complexes leading to 1-, 2-, 3-and 4-acetyl-9H-fluorene, respectively, were computed at the DFT B3LYP 6-31G** level of theory. The data serve as a basis for the discussion of the reactivity-selectivity pattern observed and it is concluded that the distribution of products is partly kinetically controlled.

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Section: Resultsmentioning

confidence: 99%

The synthesis of mono- and diacetyl-9H-fluorenes. Reactivity and selectivity in the Lewis acid catalyzed Friedel-Crafts acetylation of 9H-fluorene

Titinchi¹,

Kamounah²,

Abbo³

et al. 2008

Arkivoc

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“…[1][2][3] Aw ide range of conjugated macromolecules have been investigated, including derivatives of polyacetylene, [4,5] polyphenylene, [6] polyarylenevinylene, [7,8] polypyrrole, [9] polythiophene, [10] and polyfluorene backbones, [11,12] as well as numerous more complex structures. [1][2][3] Aw ide range of conjugated macromolecules have been investigated, including derivatives of polyacetylene, [4,5] polyphenylene, [6] polyarylenevinylene, [7,8] polypyrrole, [9] polythiophene, [10] and polyfluorene backbones, [11,12] as well as numerous more complex structures.…”

Section: Conjugated Polymers Have Attracted Tremendous Attentionmentioning

confidence: 99%

“…Conjugated polymers have attracted tremendous attention in both academia and industry as ac onsequence of their unique properties. [1][2][3] Aw ide range of conjugated macromolecules have been investigated, including derivatives of polyacetylene, [4,5] polyphenylene, [6] polyarylenevinylene, [7,8] polypyrrole, [9] polythiophene, [10] and polyfluorene backbones, [11,12] as well as numerous more complex structures. [13] This structural variability,combined with post-polymerization modification (i.e., doping), allows manipulation of the optoelectronic and physical properties,i ncluding absorption/ emission wavelengths,b and gap,H OMO/LUMO levels, conjugation length, and solubility.…”

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confidence: 99%

Click Functionalization of a Dibenzocyclooctyne‐Containing Conjugated Polyimine

2015

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A conjugated poly(phenyl-co-dibenzocyclooctyne) Schiff-base polymer, prepared through polycondensation of dibenzocyclooctyne bisamine (DIBO-(NH2)2) with bis(hexadecyloxy)phenyldialdehyde, is reported. The resulting polymer, which has a high molecular weight (M(n)>30 kDa, M(w)>60 kDa), undergoes efficient strain-promoted alkyne-azide cycloaddition reactions with a series of azides. This enables quantitative modification of each repeat unit within the polymer backbone and the rapid synthesis of a conjugated polymer library with widely different substituents but a consistent degree of polymerization (DP). Kinetic studies show a second-order reaction rate constant that is consistent with monomeric dibenzocyclooctynes. Grafting with azide-terminated polystyrene and polyethylene glycol monomethyl ether chains of varying molecular weight resulted in the efficient syntheses of a series of graft copolymers with a conjugated backbone and maximal graft density.

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“…Conjugated polymers have attracted tremendous attention in both academia and industry as a consequence of their unique properties . A wide range of conjugated macromolecules have been investigated, including derivatives of polyacetylene, polyphenylene, polyarylenevinylene, polypyrrole, polythiophene, and polyfluorene backbones, as well as numerous more complex structures . This structural variability, combined with post‐polymerization modification (i.e., doping), allows manipulation of the optoelectronic and physical properties, including absorption/emission wavelengths, band gap, HOMO/LUMO levels, conjugation length, and solubility .…”

Section: Methodsmentioning

confidence: 99%

Click Functionalization of a Dibenzocyclooctyne‐Containing Conjugated Polyimine

2015

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A conjugated poly(phenyl‐co‐dibenzocyclooctyne) Schiff‐base polymer, prepared through polycondensation of dibenzocyclooctyne bisamine (DIBO‐(NH2)2) with bis(hexadecyloxy)phenyldialdehyde, is reported. The resulting polymer, which has a high molecular weight (Mn>30 kDa, Mw>60 kDa), undergoes efficient strain‐promoted alkyne–azide cycloaddition reactions with a series of azides. This enables quantitative modification of each repeat unit within the polymer backbone and the rapid synthesis of a conjugated polymer library with widely different substituents but a consistent degree of polymerization (DP). Kinetic studies show a second‐order reaction rate constant that is consistent with monomeric dibenzocyclooctynes. Grafting with azide‐terminated polystyrene and polyethylene glycol monomethyl ether chains of varying molecular weight resulted in the efficient syntheses of a series of graft copolymers with a conjugated backbone and maximal graft density.

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Versuche zur polymerisation von fluoren

Cited by 11 publications

References 8 publications

The synthesis of mono- and diacetyl-9H-fluorenes. Reactivity and selectivity in the Lewis acid catalyzed Friedel-Crafts acetylation of 9H-fluorene

The synthesis of mono- and diacetyl-9H-fluorenes. Reactivity and selectivity in the Lewis acid catalyzed Friedel-Crafts acetylation of 9H-fluorene

Click Functionalization of a Dibenzocyclooctyne‐Containing Conjugated Polyimine

Click Functionalization of a Dibenzocyclooctyne‐Containing Conjugated Polyimine

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