Synthesis and properties of luminophores derived from fluorinated biphenyls

Ol’khovik, V. K.; Pap, A. A.; Vasilevskii, V. A.; Galinovskii, N. A.; Tereshko, S. N.

doi:10.1134/s1070428008080113

Cited by 22 publications

(19 citation statements)

References 7 publications

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“…prepared by nitration of 4,4'-biphenyldicarboxylic acid varying a published synthesis procedure[27]. Details are given in the supporting information.…”

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confidence: 99%

Four new Al-based microporous metal-organic framework compounds with MIL-53-type structure containing functionalized extended linker molecules

Halis

Reimer

Klinkebiel

et al. 2015

Microporous and Mesoporous Materials

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“…prepared by nitration of 4,4'-biphenyldicarboxylic acid varying a published synthesis procedure[27]. Details are given in the supporting information.…”

mentioning

confidence: 99%

Four new Al-based microporous metal-organic framework compounds with MIL-53-type structure containing functionalized extended linker molecules

Halis

Reimer

Klinkebiel

et al. 2015

Microporous and Mesoporous Materials

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“…the many advantages of MOFs is the ability to incorporate different functional groups within their pores. As a part of our efforts in this field, we prepared the previously reported dimethyl 2,2′-dinitrobiphenyl-4,4′-dicarboxylate (Ol'khovik et al 2008) and report its structure herein.…”

Section: Methodsmentioning

confidence: 99%

“…For the synthesis of the title compound, see: Ol'khovik et al (2008). For the structure of 2,2 0 -dinitrobiphenyl-4,4 0 -dicarboxylic acid, see: Wu et al (2010).…”

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confidence: 99%

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Dimethyl 2,2′-dinitrobiphenyl-4,4′-dicarboxylate

et al. 2014

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Key indicators: single-crystal X-ray study; T = 90 K; mean (C-C) = 0.002 Å; R factor = 0.034; wR factor = 0.096; data-to-parameter ratio = 11.8.The title compound, C 16 H 12 N 2 O 8 , exhibits two near-planar aromatic ester groups with aryl-ester dihedral angles of 2.1 (2) and 4.2 (3). The dihedral angle between the aromatic rings is 58.0 (1). The two nitro groups are tilted slightly from the plane of the aromatic rings, making dihedral angles of 14.1 (1) and 8.2 (2) . In the crystal, molecules are connected by weak C-HÁ Á ÁO interactions, forming a three-dimensional network. Related literature

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“…4,4′-bis[(E)-1-(1,3-benzoxazol-2-yl)-2-ethenyl]-2-fluorobiphenyl (BPh-1) and 4,4′-bis[(E)-1-(1,3-benzoxazol-2-yl)-2-ethenyl]-2,2′-difluorobiphenyl (BPh-2) were obtained by reaction of the corresponding fluorinated 4,4′-diformylbiphenyls with 2-methyl-1,3-benzoxazole under Knoevenagel condensation conditions [14]. The reaction proceeded with high stereoselectivity, forming only the trans-trans isomer of the target luminophores BPh-1 and BPh-2:…”

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Effect of substituents in benzoxazole derivatives of biphenyl on the optical properties and photostability of their thin films

et al. 2009

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established that fluorine atoms in the biphenyl moiety of the benzoxasole derivatives significantly improve the stability of the TVD films relative to oxidative aging compared with hexyloxy substituents. Irradiation with UV light stimulates quenching of luminescence and structuring of the TVD film of the difluoro-substituted derivative.Introduction. The spectral properties of poly(phenylene vinylenes) (PPVs), used as thin-film electroluminescent materials, depend considerably on the nature of the substituents on the PPV backbone and side chains [1-3]. Thus the electroluminescence turn-on voltage for diodes containing thin films of poly[2-(2-ethylhexyloxyl)-5-(4-trifluoromethylphenyl)-1,4-phenylene vinylene] and poly[2-(2-ethylhexyloxy)-5-(3,5-bis(trifluoromethyl)phenyl)-1,4-phenylene vinylene] as emitting layers is 4.0 V and 3.3 V respectively [4], and 18 V for poly[2-(2-ethylhexyloxy)-5-phenyl)-1,4-phenylene vinylene] not containing electron-acceptor trifluoromethylphenyl substituents [5]. Very high photoluminescence efficiency (>60%) is observed for PPV films containing alkylsilyl substituents [6].The position of the substituents also affects the photoluminescent properties of PPV, and this effect is especially important in sold samples in which the major role is played by the steric factor and intermolecular interaction. For a poly(2,3-dibutoxy)-1,4-phenylene vinylene film, not only a hypsochromic shift has been observed but also a significant increase in the photoluminescence efficiency (~40%) [7] relative to a poly(2-methoxy-5-ethylhexyloxy)-1,4-phenylene vinylene film (~15%-20%) [8,9].We should point out that introducing bulky oxyalkyl side substituents is a widely used method for improving the stability of PPV films relative to crystallization. However, it has been established [10] that in TVD films of model low-molecular weight octyloxy-substituted phenylene vinylenes, the crystal phase content is higher than in octyl-substituted analogs.According to the data in [11], substituted biphenyls have a low tendency to crystallize and are convenient for studying low-molecular weight analogs of PPV. Owing to high emissivity in the solid state and good electron transport properties, TVD films of benzoxazole derivatives of biphenyl are also promising for use in electroluminescent devices [12].We showed earlier in [13] that 2,2′-oxyhexyl substituents in the biphenyl moiety of 4,4′-bis[(E)-1-(1,3-benzoxazol-2-yl)-2-ethenyl-1,1′-biphenyl (BP) reduce the photostability and promote aggregation of hexyloxy-substituted TVD films of biphenyl on storage, while a TVD film of unsubstituted biphenyl is stable relative to irradiation and oxidative aging.

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Synthesis and properties of luminophores derived from fluorinated biphenyls

Cited by 22 publications

References 7 publications

Four new Al-based microporous metal-organic framework compounds with MIL-53-type structure containing functionalized extended linker molecules

Four new Al-based microporous metal-organic framework compounds with MIL-53-type structure containing functionalized extended linker molecules

Dimethyl 2,2′-dinitrobiphenyl-4,4′-dicarboxylate

Effect of substituents in benzoxazole derivatives of biphenyl on the optical properties and photostability of their thin films

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