Optical properties of a novel alkoxy-substituted poly (p-phenylene 1,3,4-oxadiazoles) for electro-optical devices

Mormile, Pasquale; Petti, Lucia; Gillo, M.; Laurienzo, Paola; Malinconico, Mario; Roviello, and Antonio; Lipson, Stephen M.; Blau, Werner J.

doi:10.1016/s0254-0584(02)00187-6

Cited by 32 publications

(15 citation statements)

References 10 publications

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“…The very strong absorbance in the UV range was due to an electronic π → π* transition, as these polymers have a huge π population along the main chain. The spectra of the copolymers were very similar to that of POD 8 homopolymer reported in previous research,27, 28 with negligible variations in the UV range. This characteristic confirmed the interest of these polymers for applications as UV optical filters or as coatings for shielding elements in the industrial field.…”

Section: Resultssupporting

confidence: 84%

“…The introduction of alkoxy‐substituted phenylene rings leads to improved solubility in organic solvents at increasing length of the alkoxy chain; moreover, we showed that for a chain length of eight carbon atoms the optical behavior and refractive index of the corresponding polymer (POD 8 ) are interesting for applications in many specialty fields, such as semiconductors, planar waveguides, and telecommunication 28…”

Section: Introductionmentioning

confidence: 99%

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Unsaturated alkoxy‐substituted poly(p‐phenylene 1,3,4‐oxadiazole)s: Synthesis and chemical–physical characterization

Capitani

Laurienzo

Malinconico

et al. 2003

J. Polym. Sci. A Polym. Chem.

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A new series of alkoxy-substituted poly(p-phenylene 1,3,4-oxadiazole)s modified by the insertion of small percentages of various comonomers were synthesized through the precursor polyhydrazides. The comonomers used contained trans double bonds or meta-alkoxy-substituted aromatic rings to improve the solubility of the final polymers. The synthesized copolymers were chemically characterized by 1 H NMR and Fourier transform infrared spectroscopy. In some cases, the copolymers really showed improved solubility in organic solvents. The 15 N solid-state NMR technique was applied to examine the degree of conversion from the precursor polyhydrazides to the final polymers, which determined the effective conjugated length in the target polyoxadiazoles. Thermal stability and structural characteristics of all the polymers as well as a preliminary investigation on the optical properties of polyoxadiazoles are also reported. The copolymers retained high absorbance in the UV region and high transmission in the whole telecommunication range.

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Section: Resultssupporting

confidence: 84%

Section: Introductionmentioning

confidence: 99%

Unsaturated alkoxy‐substituted poly(p‐phenylene 1,3,4‐oxadiazole)s: Synthesis and chemical–physical characterization

Capitani

Laurienzo

Malinconico

et al. 2003

J. Polym. Sci. A Polym. Chem.

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“…In addition, they show anticonvulsant [14], anti-HIV [15], and antituberculostatic activity [16]. They have also been used in pesticide chemistry [17], polymer [18], and material science [19][20][21]. Owing to their manifold activity, still new oxadiazole derivatives are synthesized and examined for their biological activity to search for and develop desired properties such as, for example, analgesic, antiviral, or anticancer activity [5,22].…”

Section: Introductionmentioning

confidence: 99%

On constitutional isomers and tautomers of oxadiazolones and their mono- and disulfur analogues (C2H2N2XY; X,Y=S,O)

Karpińska

Dobrowolski

2013

Computational and Theoretical Chemistry

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a b s t r a c tThe constitutional isomers and tautomers of oxadiazolones, as well as their mono-and disulfur analogues, were calculated at the B3LYP/aug-cc-pVDZ level. Four groups of 30 molecules each were considered: oxadiazolone, oxadiazolthione, thiadiazolone, and thiadiazolthione isomers. The compounds were categorized into six groups according to permutations of three heteroatoms in the five-membered ring. Additionally, each of the constitutional isomer was considered to have five tautomers conserving stable five-membered ring: two NH tautomers, two rotameric OH (or SH) forms and one CH 2 tautomer. It appeared that the largest difference between oxadiazolone O and S analogues is produced by the kind of chalcogen atom in the ring, which is strained when the O atom is in the ring while much less strained when the S-atom, of much larger van der Waals radius, is built into the ring. The external chalcogen is only modifying the general energetic factors. The comparison of energetics of analogous groups of molecules with thiadiazole and oxadiazole rings is done in details as well as differences resulting from different external chalcogen atoms are discussed as well. The presence of water surrounding was mimicked with the IEF-PCM implicit water model which did not change general isomer relative stability picture, but for some special cases indicated an extra stability of the forms with external OH or SH groups. The aromaticity monitored by the structural HOMA aromaticity index shows that the systems are not additionally stabilized by pi-electron delocalization. The fair linear correlation between the aromaticity indices of oxadiazolones and oxadiazolthiones shows that the pi-electron system in the studied systems is not sensitive to change of the external chalcogen group.

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“…Because of their excellent heat and solvent resistance, they have been used for high‐performance materials. Recently, their optical and electronic properties have been receiving attention to create novel devices13–17 as well as high‐performance materials 18–24. Because they have limited solubility in common organic solvents, they are generally processed from the soluble polyhydrazide precursors.…”

Section: Introductionmentioning

confidence: 99%

Thermally induced solid‐state synthesis of fluorine‐containing poly(ether oxadiazole)

Maruyama

Maeda

Wakabayashi

et al. 2010

J of Applied Polymer Sci

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Synthesis of poly [oxy-(2,3,5,6-tetrafluoro-1,4-phenylene)-(1,3,4-oxadiazol-2-yl)-1,4-phenylene] (F-PEOz) was examined by nucleophilic aromatic substitution reaction of 2-(4-hydroxyphenyl)-5-pentafluorophenyl-1,3,4-oxadiazole (HPOz). Only low molecular weight F-PEOz or crosslinked insoluble polymers were obtained by the solution polymerization with bases. In contrast, thermally induced solid-state polymerization of HPOz potassium salts at 180C for 1 h gave fully soluble F-PEOz with the yield of 84% and its reduced viscosity was 0.66 dL g À1 . The longer polymerization time gave insoluble polymers due to the crosslinking reaction even in solid state. The solid-state polymerization did not undergo topochemically and it proceeded in an amorphous state. The crosslinking reaction was slightly inhibited by the solid-state polymerization. F-PEOz exhibited excellent solubility, high T g of 246 C and good thermal stability.

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Optical properties of a novel alkoxy-substituted poly (p-phenylene 1,3,4-oxadiazoles) for electro-optical devices

Cited by 32 publications

References 10 publications

Unsaturated alkoxy‐substituted poly(p‐phenylene 1,3,4‐oxadiazole)s: Synthesis and chemical–physical characterization

Unsaturated alkoxy‐substituted poly(p‐phenylene 1,3,4‐oxadiazole)s: Synthesis and chemical–physical characterization

On constitutional isomers and tautomers of oxadiazolones and their mono- and disulfur analogues (C2H2N2XY; X,Y=S,O)

Thermally induced solid‐state synthesis of fluorine‐containing poly(ether oxadiazole)

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