Synthesis and Characterization of Novel Polyesters and Polyurethanes Containing 9,10-Diethynylanthracene and Pyromellitic Diimide

Fomine, Serguei; Marin, Margarita; Fomina, Lioudmila; Salcedo, Roberto; Sansores, Enrique; Méndez, José Manuel Gómez y; Jimenez, Cristina Flores; Ogawa, Teiichiro

doi:10.1295/polymj.28.641

Cited by 19 publications

(25 citation statements)

References 15 publications

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“…Similar 1 H NMR spectrum was observed in the polymer prepared by the free radical polymerization of the nonsubstituted cyclic monomer, MDS. 25 The 13 C NMR spectrum of poly(MDS-Cl) obtained by the free radical polymerization is presented in Figure 2a. In addition to the peaks attributed to the aromatic carbons at 123-145 ppm, two characteristic peaks are clearly observed at 49.0 and 33.7 ppm, which are attributable to two different aliphatic carbons in the polymer backbone formed by the ring-opening process of MDS-Cl.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and Optoelectronic Properties of Alternating Copolymers Containing Anthracene Unit in The Main Chain by Radical Ring-Opening Polymerization

2010

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Novel alternating copolymers composed of anthracene moiety and halostyrene unit were synthesized by ring-opening polymerization of cyclic monomers, 10-methylene-9,10-dihydroanthryl-9-spirop-chlorophenylcyclopropane and its bromo derivative. Reversible addition-fragmentation chain transfer and conventional free radical polymerizations were employed for the purpose. In both cases, the ring-opening polymerization proceeded predominantly to afford alternating copolymer containing anthracene unit in the main chain. Incorporations of optoelectronic groups, involving diphenylamine, carbazole, and phenothiazine, on the halostyrene moieties of the alternating copolymers were conducted by palladium-catalyzed reactions. Novel nonconjugated copolymers having perfect alternating structures were obtained, in which the alternate arrangement of two distinct electronic functionalities is formed owing to the ring-opening polymerization system. Resulting anthracene-based alternating copolymers having two distinct electronic functionalities exhibited characteristic fluorescence resonance energy transfer, as confirmed by UV-vis and fluorescence spectra.

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Section: Resultsmentioning

confidence: 99%

“…13 C NMR spectra (CDCl 3 ) of polymers obtained by (a) free radical polymerization of 10-methylene-9,10-dihydroanthryl-9-spiro-pchlorophenylcyclopropane (MDS-Cl), (b) reversible addition-fragmentation chain transfer (RAFT) polymerization of MDS-Cl, and (c) RAFT polymerization of 10-methylene-9,10-dihydroanthryl-9-spiro-pbromophenylcyclopropane (MDS-Br).…”

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confidence: 99%

Synthesis and Optoelectronic Properties of Alternating Copolymers Containing Anthracene Unit in The Main Chain by Radical Ring-Opening Polymerization

2010

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“…We published recently a series of studies on the synthesis of polymers containing discrete conjugated units of fluorescein, 8 • 9 diethynylantracene, 10 vinylphenylantracene, 11 and arylenevinylideneethynylene. 12 All these polymers gave films with good optical quality on casting.…”

Section: Coumarinmentioning

confidence: 99%

Polymers from Coumarines. Synthesis and Characterization of Polyamides Derived from 6-{[3-(Chloroformyl)phenyl]ethynyl}coumarin-3-carboxylic Acid Chloride

Fomine

Fomina

Sánchez

et al. 1997

Polym J

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ABSTRACT:Coumarin-containing polyamides from 6-{[3-(chloroformyl)phenyl]ethynyl}coumarin-3-carboxylic acid chloride were prepared and characterized for the first time. They were soluble in common organic solvents such as Nmethylpyrrolidone (NMP) and dimethyl sulfoxide (DMSO) and gave transparent and tough films on casting. In the presence of excess diamine, the polymers underwent chemical transformation at room temperature, producing polyazomethynes, as confirmed by the corresponding model reactions, and a possible reaction mechanism is proposed for this transformation. The coumarin containing polyamides showed emission and excitation maxima peaking at 464 and 398 nm, respectively, in solution and exhibited I 0% weight loss above 400°C.KEY WORDS Coumarin / Polyamides / Photoluminescence / Coumarines (1,2-benzopyrones) and a class ofheterocycles known for fluorescent properties. They are widely used as laser dyes 1 ' 2 due to high photostability and quantum yield of photoluminescence. The chemical modification of coumarines makes it possible to vary emission wavelength continuously throughout visible spectrum. 3 Coumarines were also found to be electroluminescent. Thus, a dispersion of coumarin 6 in polymethylmethacrylate showed electroluminescence 4 peaking at 554 nm. Et_ Coumarin 6Although many papers have been published on the synthesis and characterization of coumarines and various reviews are available 3 • 5 very little attention has been paid to the incorporation of coumarines into polymers and only two papers have been published on this topic. The radical copolymerization of coumarin with styrene was studied by Yun. 6 Polyesters containing a coumarin dimer were obtained by the photopolymerization of 7,7'-coumarinylpolymethylene dicarbonates. 7 In these cases, the double bond of coumarin participates in the polymerization giving polymers containing derivatives of 3,4-dihydrocoumarin which do not have interesting optical properties because of the disturbing of the conjugation. On the other hand, polymeric materials containing emitter units have advantage over low molecular weight analogies, especially in making of electroluminescence devices; because of the absence of phase separation, and the possibilities of preparation of thin films of any desirable dimension with high optical quality by simple casting.t To whom correspondence should be addressed.We published recently a series of studies on the synthesis of polymers containing discrete conjugated units of fluorescein, 8 • 9 diethynylantracene, 10 vinylphenylantracene, 11 and arylenevinylideneethynylene. 12 All these polymers gave films with good optical quality on casting. Fluorescein-containing polymers exhibited nonlinear optical susceptibility of the third order of 3 x 10-10 esu, while anthracene-containing polymers showed electroluminescence at voltage as low as 6 V.This work describes the synthesis and characterization of polyamides containing 3,6-disubstituted coumarine units for the first time. EXPERIMENT AL Materials1,2-Dichlorobenzene was purifie...

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“…5,6 Certain anthracene-containing polymers have been recently synthesized. [7][8][9][10][11][12][13] This investigation deals with the synthesis and characterization of a new class of photoluminescent polyesters and polyethers bearing substituted m-terphenyl segments in the main chain. They were prepared from two bisphenols that were synthesized through pyrylium salts by a convenient and inexpensive method applied in our laboratory.…”

Section: Introductionmentioning

confidence: 99%

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

Mikroyannidis

2000

J. Polym. Sci. A Polym. Chem.

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Synthesis and Characterization of Novel Polyesters and Polyurethanes Containing 9,10-Diethynylanthracene and Pyromellitic Diimide

Cited by 19 publications

References 15 publications

Synthesis and Optoelectronic Properties of Alternating Copolymers Containing Anthracene Unit in The Main Chain by Radical Ring-Opening Polymerization

Synthesis and Optoelectronic Properties of Alternating Copolymers Containing Anthracene Unit in The Main Chain by Radical Ring-Opening Polymerization

Polymers from Coumarines. Synthesis and Characterization of Polyamides Derived from 6-{[3-(Chloroformyl)phenyl]ethynyl}coumarin-3-carboxylic Acid Chloride

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

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