Synthesis and properties of soluble, fluorescent polyesters and polyethers with substitutedm-terphenyl segments in the main chain

Mikroyannidis, John A.

doi:10.1002/1099-0518(20000701)38:13<2381::aid-pola110>3.0.co;2-u

Cited by 5 publications

(7 citation statements)

References 24 publications

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“…With 4 , polyesters and poly(alkyl ether)s with low values of η inh were reported by Mikroyannidis 22. In this work, poly(arylene ether)s were prepared by the polycondensation of 4 with various activated difluoro monomers ( 7a – 7f ).…”

Section: Resultsmentioning

confidence: 76%

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Synthesis and characterization of soluble, fluorescent poly(arylene ether)s, poly(arylene thioether)s, and poly(arylene sulfone)s containing 1,3,5‐triphenylbenzene segments

Shaikh

Hay

2002

J. Polym. Sci. A Polym. Chem.

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The bisphenol 4,4Љ-dihydroxy-5Ј-phenyl-m-terphenyl (4), containing a 1,3,5-triphenylbenzene moiety, was synthesized from a pyrylium salt obtained by the reaction of benzaldehyde with p-methoxyacetophenone with boron trifluoride etherate as a condensing agent. Polymers were obtained from 4 by a nucleophilic displacement reaction with various activated difluoro monomers and with K 2 CO 3 as a base. A series of new poly(arylene ether)s (8a-8f) were obtained that contained phenyl-substituted m-terphenyl segments in the polymer chain. Polymers with inherent viscosities of 0.41-0.99 dL/g were obtained in yields greater than 96%. The polymers were soluble in a variety of organic solvents, including nonpolar solvents such as toluene. Clear, transparent, and flexible films cast from CHCl 3 showed high glass-transition temperatures (T g ϭ 198 -270°C) and had excellent thermal stability, as shown by temperatures of 5% weight loss greater than 500°C. 4 was converted via N,N-dimethyl-Othiocarbamate into the masked dithiol 4,4Љ-bis(N,NЈ-dimethyl-S-thiocarbamate)-5Јphenyl-m-terphenyl and was polymerized with activated difluoro compounds in the presence of a mixture of Cs 2 CO 3 and CaCO 3 as a base in diphenyl sulfone as a solvent. A series of new poly(arylene thioether)s (9a-9e) were obtained with T g values similar to those of 8a-8e. 9a-9e were further oxidized into poly(arylene sulfone)s with T g values 40 -80°C higher than those for 8a-8e and 9a-9e. These polymers also had good solubility in organic solvents. A sulfonic acid group was selectively introduced onto the pendent phenyl group of polymers 8a and 8f by reaction with chlorosulfonic acid. The polymers were soluble in dipolar aprotic solvents and formed films via casting from dimethylformamide. Polymers 8a-8f, 11a, and 11f showed blue and red fluorescence under ultraviolet-visible light with emission maxima at 380 -440 nm.

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Section: Resultsmentioning

confidence: 76%

“…Compound 2 has been reported in the literature, and its melting point is 135 °C. The synthesis of 2 was reported with the same reaction scheme22 while our work was still in progress. The reported yield of 2 was 87% with a melting point of 92–94 °C, 40 °C lower than the literature value 13.…”

Section: Resultsmentioning

confidence: 94%

Synthesis and characterization of soluble, fluorescent poly(arylene ether)s, poly(arylene thioether)s, and poly(arylene sulfone)s containing 1,3,5‐triphenylbenzene segments

Shaikh

Hay

2002

J. Polym. Sci. A Polym. Chem.

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“…An analogous behavior has been observed in our previously synthesized polyethers. 26 Interestingly, all polymers were entirely insoluble in H 4 SO 4 98%, even upon heating, and their ionic nature should be responsible for this feature.…”

Section: Crystallinity Hydrophilicity and Solubility Of Polymersmentioning

confidence: 99%

“…Furthermore, it seems that the length of the aliphatic spacer in the backbone of polyethers TA1 and TA2 did not alter the emission curves, that conforms with our data. 26 The photoluminescence spectra of TA1 and TA2 showed red-shifted maxima upon going from solution to the solid state. This feature was attributed to considerable stacking interactions in solid state and the formation of aggregates.…”

Section: Optical Properties Of Polymersmentioning

confidence: 99%

“…Solubilities of Polymers our previously synthesized analogous polymers. 26 More particularly, polyester S (Chart 3) displayed in THF solution emission maxima at 401 and 420 nm, which are blue-shifted by 16 nm as compared with the present polyester SA. It is well established that the quaternization of the ring nitrogen atom increases the emission wavelengths of the polymers.…”

Section: Optical Properties Of Polymersmentioning

confidence: 99%

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Soluble, photoluminescent, ionic polymers with 2,6-bisphenyl-4-anthracenyl-N-hexadecylpyridinium tetrafluoroborate segments

Mikroyannidis

2000

J. Polym. Sci. A Polym. Chem.

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Synthesis of poly(p‐phenylene vinylene)‐ and poly(phenylene ethynylene)‐based polymers containing p‐terphenyl in the main chain with alkoxyphenyl side groups

Spiliopoulos

Mikroyannidis

2002

J. Polym. Sci. A Polym. Chem.

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Starting from the pyrylium salt and following a facile synthetic route, we synthesized and polymerized 4,4″‐diiodo‐2′,6′‐di[4‐(2′‐ethylhexyl)oxy]phenyl‐p‐terphenyl with p‐divinylbenzene or p‐diethynylbenzene. The resulting polymers had moderate molecular weights, were amorphous, and dissolved in tetrahydrofuran and chloroform, with glass‐transition temperatures of 120–131 °C. The polymers behaved as violet‐blue‐emitting materials with photoluminescence maxima around 420 and 450 nm in solution and in thin films, respectively. They possessed well‐defined chromophores resulting from steric interactions in the polymer chain. The photoluminescence quantum yields were up to 0.29. © 2002 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 40: 2591–2600, 2002

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Synthesis and properties of soluble, fluorescent polyesters and polyethers with substitutedm-terphenyl segments in the main chain

Cited by 5 publications

References 24 publications

Synthesis and characterization of soluble, fluorescent poly(arylene ether)s, poly(arylene thioether)s, and poly(arylene sulfone)s containing 1,3,5‐triphenylbenzene segments

Synthesis and characterization of soluble, fluorescent poly(arylene ether)s, poly(arylene thioether)s, and poly(arylene sulfone)s containing 1,3,5‐triphenylbenzene segments

Soluble, photoluminescent, ionic polymers with 2,6-bisphenyl-4-anthracenyl-N-hexadecylpyridinium tetrafluoroborate segments

Synthesis of poly(p‐phenylene vinylene)‐ and poly(phenylene ethynylene)‐based polymers containing p‐terphenyl in the main chain with alkoxyphenyl side groups

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