Isomeric Poly(benzophenone)s: synthesis of Highly Crystalline Poly(4,4'-benzophenone) and Amorphous Poly(2,5-benzophenone), a Soluble Poly(p-phenylene) Derivative

Phillips, Ralph W.; Sheares, Valerie V.; Samulski, Edward T.; DeSimone, Joseph M.

doi:10.1021/ma00086a064

Cited by 53 publications

(47 citation statements)

References 9 publications

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“…The max numbers for the three polymers are 356, 355, and 363 nm for P1, P2, and P3, respectively. This is in good agreement with the max of 354 nm we determined for poly(2,5-benzophenone) previously 15 and the max of 352 nm of poly (2,5-benzophenone) determined by Wang and Quirk 18 indicating that P1-P3 are highly conjugated materials. The UV-vis spectrum of P2 is shown in Figure 7.…”

Section: Polymer Synthesis and Characterizationsupporting

confidence: 92%

“…DeSimone et al have previously reported on the synthesis of poly(2,5-benzophenone) from 2,5-dichlorobenzophenone utilizing this catalyst sytem. 15 Maxdem Inc. 16,17 has also reported the synthesis of poly(2,5-benzophenone) in a similar manner but with different glass transition and thermal decomposition temperatures. Wang and Quirk 18 have reported that higher glass transition temperatures, which result from a more stereoregular head-to-tail geometry in the polymer backbone, are obtained when 2,2-dipyridyl is used as a coligand in the reaction.…”

Section: Introductionmentioning

confidence: 97%

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Alkyl-substituted poly(2,5-benzophenone)s synthesized via Ni(0)-catalyzed coupling of aromatic dichlorides and their miscible blends

Pasquale

Sheares

1998

J. Polym. Sci. A Polym. Chem.

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High molecular weight poly(2,5‐benzophenone) derivatives were prepared by Ni(0)‐catalyzed coupling of 4′‐substituted 2,5‐dichlorobenzophenones. Monomers were synthesized by the Friedel–Crafts reaction of 2,5‐dichlorobenzoyl chloride and alkyl‐substituted benzenes in the presence of aluminum chloride. The resulting polymers are soluble and show no evidence of crystallinity by DSC. Number average molecular weights are in the range of 9.2 × 103–11.7 × 103 g/mol by multiple angle laser light scattering (MALLS). Molecular weights obtained by MALLS are only slightly lower (∼90%) than those obtained by GPC (polystyrene standards). These polymers exhibit high thermal stability with glass transition temperatures ranging from 173 to 225°C and weight loss occurring above 450°C in nitrogen and 430°C in air. Additionally, the polymers were blended and the resulting polymer films appear to be miscible by DSC results. © 1998 John Wiley & Sons, Inc. J. Polym. Sci. A Polym. Chem. 36: 2611–2618, 1998

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Section: Polymer Synthesis and Characterizationsupporting

confidence: 92%

Section: Introductionmentioning

confidence: 97%

Alkyl-substituted poly(2,5-benzophenone)s synthesized via Ni(0)-catalyzed coupling of aromatic dichlorides and their miscible blends

Pasquale

Sheares

1998

J. Polym. Sci. A Polym. Chem.

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“…Bandgaps observed for alkoxysubstituted PPPs are larger than that of PPP but smaller than that of alkyl-substituted analogues, because an alkoxy group is less sterically demanding than an equivalent alkyl substituent [98]. Other interesting PPP derivatives are those containing benzoyl substituents [99], which have an estimated bandgap of 2.8 eV and exhibit blue luminescence [100]. It is also worth mentioning that bandgaps measured for copolymers containing substituents only in alternate units are smaller than those of the corresponding homopolymers with substituents in all the phenyl rings, which reflects the greater planarity achievable with fewer side groups.…”

Section: Modulation Of Electronic Properties Of Conjugated Polymers Tmentioning

confidence: 99%

The chemistry of electroluminescent organic materials

Segura¹

1998

Acta Polym.

287

200

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Electroluminescence has been a subject of interest for several decades because of its many applications in areas such as telecommunications or information displays. Light‐emitting diodes using p‐n junctions of inorganic semiconductors have dominated the field in the last twenty years; however, efficient blue emission has only recently been achieved and inorganic semiconductors are difficult to form over large areas, making the process uneconomic. During the last decade, an explosive growth of activity in the area of organic electroluminescence has occurred in both academia and industry, stimulated by the promise of light‐emitting plastics for the fabrication of large, flexible, inexpensive and efficient screens to be used in different applications. Thus, a substantial amount of research is presently directed towards color control and improvement of manufacturability and reliability of devices in order to make their commercialization viable. A great deal of work has been carried out by physicists and materials scientists concerned with the preparation of different device structures and with the use of different techniques for device manufacture. However, all this work would not be possible without the continuous efforts of synthetic chemists to prepare materials with enhanced luminescent properties and processabilities. This article provides a review of the main types of organic materials that have been used in the fabrica‐tion of light‐emitting diodes either as emitting materials or as charge‐transport layers. Special attention will be paid to the different synthetic strategies that have been followed in order to tune the color of the emission, to increase stability of materials and to enhance their processabilities.

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“…Broad and strong absorption band at about 3 300 cm À1 was assigned to the -OH absorption band in FT-IR spectra. [6,7] In Figure 1, the FT-IR spectra of copolymers displayed no broad and strong -OH absorption band at about 3 300 cm À1 which was relative to reduction of carbonyl functionalities, which gave good proofs that no reduction of carbonyl functionalities could be observed in copolymerization. The 19 F NMR spectrum of PI-50 ( Figure 2) exhibits four peaks of fluorine atoms integrated in the ratio of 2:1:1:1.…”

Section: Copolymer Synthesis and Characterizationmentioning

confidence: 91%

“…[7] The inability to form flexible films greatly limited their applications such as gas-separation membranes and also their use in organic electronics. In order to extend the function of polyphenylenes, several methods have been developed to prepare PPPs with improved film-forming capacity.…”

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confidence: 99%

Synthesis and Properties of Novel Fluorinated Poly(phenylene‐co‐imide)s

Zhang

Chen

et al. 2007

Macro Chemistry & Physics

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A new class of high‐performance materials, fluorinated poly(phenylene‐co‐imide)s, were prepared by Ni(0)‐catalytic coupling of 2,5‐dichlorobenzophenone with fluorinated dichlorophthalimide. The synthesized copolymers have high molecular weights ($\overline M _{\rm w}$ = 5.74 × 104–17.3 × 104 g · mol−1), and a combination of desirable properties such as high solubility in common organic solvent, film‐forming ability, and excellent mechanical properties. The glass transition temperature (Tgs) of the copolymers was readily tuned to be between 219 and 354 °C via systematic variation of the ratio of the two comonomers. The tough polymer films, obtained by casting from solution, had tensile strength, elongation at break, and tensile modulus values in the range of 66.7–266 MPa, 2.7–13.5%, and 3.13–4.09 GPa, respectively. The oxygen permeability coefficients ($P_{{\rm O}_{\rm 2} }$) and permeability selectivity of oxygen to nitrogen ($P_{{\rm O}_{\rm 2} } /P_{{\rm N}_{\rm 2} }$) of these copolymer membranes were in the range of 0.78–3.01 barrer [1 barrer = 10−10 cm3 (STP) cm/(cm2 · s · cmHg)] and 5.09–6.25, respectively. Consequently, these materials have shown promise as engineering plastics and gas‐separation membrane materials.

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Isomeric Poly(benzophenone)s: synthesis of Highly Crystalline Poly(4,4'-benzophenone) and Amorphous Poly(2,5-benzophenone), a Soluble Poly(p-phenylene) Derivative

Cited by 53 publications

References 9 publications

Alkyl-substituted poly(2,5-benzophenone)s synthesized via Ni(0)-catalyzed coupling of aromatic dichlorides and their miscible blends

Alkyl-substituted poly(2,5-benzophenone)s synthesized via Ni(0)-catalyzed coupling of aromatic dichlorides and their miscible blends

The chemistry of electroluminescent organic materials

Synthesis and Properties of Novel Fluorinated Poly(phenylene‐co‐imide)s

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