Polybenzyls

Tsonis, Christos P.

doi:10.1016/b978-0-08-096701-1.00167-1

Cited by 5 publications

(3 citation statements)

References 29 publications

(22 reference statements)

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“…Besides, these reactions are widely used in polymer chemistry, and in fact, the first communication on formation of a viscous resin from the reaction of benzyl chloride and aluminum trichloride was reported more than 100 years ago by Friedel and Crafts . Since then, many reports on the preparation of polymers (first mainly via polyalkylation reactions, later via polyacylation as well) have been published. − Cheaply available monomers and the promising properties of the polymers that might be obtained have greatly stimulated interest in that field.…”

Section: Introductionmentioning

confidence: 99%

Superacid-Catalyzed Polycondensation of Acenaphthenequinone with Aromatic Hydrocarbons

et al. 2005

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A novel series of linear, high molecular weight polymers were synthesized by one-pot, superacid-catalyzed reaction of acenaphthenequinone (1) with aromatic hydrocarbons. The reactions were performed at room temperature in the Brønsted superacid CF3SO3H (trifluoromethanesulfonic acid, TFSA) and in a mixture of TFSA with methanesulfonic acid (MSA) and trifluoroacetic acid (TFA), which was used as both solvent and a medium for generation of electrophilic species from acenaphthenequinone. The polymer-forming reaction was found to be dependent greatly on the acidity of the reaction medium, as judged from the viscosity of the polymers obtained. Polycondensations of acenaphthenequinone with 4,4‘-diphenoxybenzophenone (f), 1,3-bis(4-phenoxybenzoyl)benzene (g), 1,4-bis(4-phenoxybenzoyl)benzene (h), 1,10-bis(4-phenoxyphenyl)decane-1,10-dione (i), 2,6-diphenoxybenzonitrile (j), 2,6-diphenoxybenzoic acid (k), and 2-(4-biphenylyl)-6-phenylbenzoxazole (l) proceeded in a reaction medium of wide range of acidity, including pure TFSA (Hammett acidity function H 0 of pure TFSA is −14.1), whereas condensation of 1 with biphenyl, terphenyl, diphenyl ether, and 1,4-diphenoxybenzene needed a reaction medium of acidity H 0 less than −11.5. A possible reaction mechanism is suggested. The polymers obtained were found to be soluble in the common organic solvents, and flexible transparent films could be cast from the solutions. 1H and 13C NMR analyses of the polymers synthesized revealed their linear, highly regular structure. The polymers also possess high thermostability. Char yields for polymers 3a, 3c, 3d, and 3l in nitrogen were close to 80% at 1000 °C.

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Section: Introductionmentioning

confidence: 99%

Superacid-Catalyzed Polycondensation of Acenaphthenequinone with Aromatic Hydrocarbons

et al. 2005

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“…Applying standard Friedel−Crafts conditions (e.g., AlCl 3 in methylene chloride or CS 2 ) led neither to a regioselective coupling nor to high molecular weight products. However, our recent reports on superacid-catalyzed Friedel−Crafts-type polycondensations impressively demonstrated the regioselective formation of linear, high molecular weight polymers. − Moreover, it is also important to note that this reaction scheme allows for the preparation of metal-free polymers of very high structural regularity.…”

Section: Resultsmentioning

confidence: 99%

A High Molecular Weight Aromatic PhOLED Matrix Polymer Obtained by Metal-Free, Superacid-Catalyzed Polyhydroxyalkylation

Hernández¹,

Zolotukhin²,

Maldonado

et al. 2009

Macromolecules

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“…Friedel−Crafts aromatic substitution reactions − alkylation and acylation − are some of the most fundamental reactions in organic chemistry and have been widely (first mainly via polyalkylation reactions, later via polyacylation as well) explored in polymer chemistry. , …”

Section: Introductionmentioning

confidence: 99%

Factors Enhancing the Reactivity of Carbonyl Compounds for Polycondensations with Aromatic Hydrocarbons. A Computational Study

2004

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For the first time, reactions of acetophenone, 2,2,2-trifluoroacetophenone, fluorenone, and dinitrofluorenones with diphenyl and 4,4′-diphenoxybenzophenone in trifluoromethanesulfonic acid (TFSA) have been studied theoretically at the B3LYP/cc-pvtz(-f)//B3LYP/6-31G* level of theory as a model reaction for a superelectrophile involving polycondensation. It was found that the introduction of electronwithdrawing groups into the carbonyl compound reduces activation and total reaction energies of the aromatic electrophilic substitution reaction. The enhancement of the reactivity of carbonyl compounds bearing electron-withdrawing groups is due to lowering of LUMO energy. The electrophiles having highly delocalized LUMO are less active in the reaction of electrophilic aromatic substitution due to decreases of local LUMO density at the reaction center. General rules for the design of reactive monomer are formulated on the basis of calculational results.

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Polybenzyls

Cited by 5 publications

References 29 publications

Superacid-Catalyzed Polycondensation of Acenaphthenequinone with Aromatic Hydrocarbons

Superacid-Catalyzed Polycondensation of Acenaphthenequinone with Aromatic Hydrocarbons

A High Molecular Weight Aromatic PhOLED Matrix Polymer Obtained by Metal-Free, Superacid-Catalyzed Polyhydroxyalkylation

Factors Enhancing the Reactivity of Carbonyl Compounds for Polycondensations with Aromatic Hydrocarbons. A Computational Study

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