Polymerization using palladium (II) salts: Homopolymers and copolymers from phenylethynyl compounds and aromatic bromides

Trumbo, David L.; Marvel, C. S.

doi:10.1002/pola.1986.080240924

Cited by 122 publications

(51 citation statements)

References 11 publications

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“…Several other groups have also employed the Heck reaction for the synthesis of novel polymers including, for example, polycinnamamides of rather high molecular weights (M -n = 93 000) 92) , cinnamoyl skeleton polyesters 93) , or main-chain liquid-crystalline polymers with distyrylbenzene mesogenic groups 94) . The Pd-catalyzed Heck-Cassar-Sonogashira-Hagihara coupling reaction of aryl dibromides or -iodides with ethynylenes is also widely used, and represents a versatile method for the synthesis of conjugated poly(arylene ethynylene)s. In general, dihalogenated aryl or heteroaryl compounds can react with terminal diethynyl compounds and form polymers according to Scheme 3 a 59,[95][96][97][98] . It is not surprising that scientists carrying out research in the field of conjugated polymers have been stimulated by the excellent yields and the mild reaction conditions; most prominently, poly(p-phenylene ethynylene)s (PPEs) are routinely synthesized with this procedure 99) and PPEs with number-average degrees of polymerization of up to 125 are readily prepared by this method 100) .…”

Section: Indirect Methods For the Synthesis Of Poly(p-phenylene Alkylmentioning

confidence: 99%

Poly(p-phenylene alkylene)s – A forgotten class of polymers

Steiger

Tervoort

Weder³

et al. 2000

Macromol. Rapid Commun.

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Within the wealth of hydrocarbon polymers, poly(p‐phenylene alkylene)s (“alkarotics”) hold a special position since they have been a long forgotten class of hydrophobic polymers. This is somewhat surprising, since the cornerstones of this polymer family cover extremely broad materials properties and the few known representatives attract attention with very favorable characteristics. In the course of this article, four new representatives of this family are presented. Whereas poly(p‐phenylene octylene) (PPPO; 90°C), poly(p‐phenylene hexylene) (PPPH; 120°C) and poly(p‐phenylene propylene) (PPPPr; 110–130°C) have surprisingly low melting temperatures, the highly crystalline poly(p‐phenylene butylene) (PPPB), melting between 200 and 225°C, meets many of the requirements that are essential for a novel, hydrophobic, processable, engineering polymer. In connection with the efforts to tailor the melting temperature of these polymers, a simple, semi‐empirical methodology to estimate melting temperatures of unknown representatives of homologous series of polymers was developed and verified. By means of this approach, the melting temperatures of PPPH and PPPB could be predicted with remarkable accuracy. In addition, it was shown that the method is not restricted to the present alkarotic polymers, but it seems to have a rather broad range of applications as shown by the successful description of the polymer series, including various liquid‐crystalline hydrocarbon polymers and different polyamides.

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Section: Indirect Methods For the Synthesis Of Poly(p-phenylene Alkylmentioning

confidence: 99%

Poly(p-phenylene alkylene)s – A forgotten class of polymers

Steiger

Tervoort

Weder³

et al. 2000

Macromol. Rapid Commun.

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“…[19] Conjugated polymers have been prepared in a diverse range of architectures, such as linear polymers, dendrimers, [20] hyperbranched polymers, [21] and networks. [22,23] Conjugated polymer chains are often rigid and inflexible, and these materials typically have poor solubility. It is therefore often necessary to introduce solubilizing side chains (or peripheral groups, in the case of dendrimers) to improve solubility in common organic solvents or in water.…”

Section: Conjugated Polymersmentioning

confidence: 99%

Conjugated Microporous Polymers

Cooper¹

2009

Advanced Materials

949

569

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Conjugated microporous polymers are of great interest because they have potential to combine high surface areas in the dry state with physical properties relevant to organic electronics. A series of recent reports has shown that materials such as poly(aryleneethynylene)s (PAEs), poly(phenyl‐ene butadiynylene)s, poly(phenylene vinylene), poly(p‐phenylene)s, polysilanes, polyanilines, and polytriazines can be produced as microporous networks with apparent Brunauer–Emmett–Teller surface areas of more than 1000 m2 g−1 in some cases. Micropore size and surface area can be synthetically fine tuned in amorphous PAE polymers and copolymers, something which was previously thought to be the preserve of ordered crystalline materials such as metal organic frameworks. We review in this Research News article recent progress made by our group and others with particular emphasis on the possible future applications of these materials.

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“…further purification a 1) 2-methyl -(3-nitrophenyl ) -3-buthyn -2-01 ( I ) [5] To the solution consisting of triethylamine (150m1) and pyridine (750ml) , 3-vitro brombenzene (40.5g ) and 2-methyl -3 -buthyn -2-01 were added and N2 -bubbled . To the mixture , triphenylphosphine (0.93g ) , copper iodide (0.4g ) and bis-triphenylphosphine palladium chloride (0.4g ) were added under N2 stream and stirred at 80°C for 1 hr .…”

Section: Experi Mentalmentioning

confidence: 99%

“…2) 3 -ni tro -ethnyl benzene ( U ) [5] To the viscous liquid, toluene (180 ml) , KOH (3g ) and methanol (20 ml ) were added and heated . Toluene was distilled out untill the peak of ( I ) disappeared on gas chromatogram.…”

Section: Experi Mentalmentioning

confidence: 99%