Preparation and Polymerization of Benzaldehyde Formaldehyde Azine (1-Phenyl-2,3-diaza-1,3-butadiene)

Hashidzume, Akihito; Tsuchiya, A.; Morishima, Yotaro; Kamachi, Mikiharu

doi:10.1021/ma991529n

Cited by 13 publications

(4 citation statements)

References 24 publications

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“…51,52 These asymmetric azines were prepared from the corresponding hydrazone and formaldehyde. Benzaldehyde formaldehyde azine (CH 2 ¼ ¼NAN¼ ¼CHC 6 H 5 , BzFAz) was unstable in bulk and formed polymer at ambient temperatures.…”

Section: 3-diazabutadienes (Azines)mentioning

confidence: 99%

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Synthesis and polymerizability of CN monomers

Hall

Padías

Kamachi

et al. 2012

J. Polym. Sci. A Polym. Chem.

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The synthesis and polymerizability of imine C¼ ¼N monomers is surveyed. The investigated imines were either far more reactive than similarly substituted C¼ ¼C or C¼ ¼O monomers, or too stable to polymerize. Imines with electron-attracting substituents on N favor polymerization by anionic mechanism, but led only to low molecular weight polymers. Imines with a donor substituent on N, such as N-arylmethyleneimines, polymerized by cationic or anionic mechanism. 1-and 2-Aza-1,3-butadienes were also rather unstable and polymerized to oligomers. The symmetrically substituted 2,3-diaza-1,3-butadienes could be purified and polymerized successfully using anionic initiators, resulting in both 1,4-and 1,2-structures in the polymer backbone, depending on the substituents. KEYWORDS: anionic polymerization; azo polymers; oligomers; polyimines INTRODUCTION Polymerizations involving olefin C¼ ¼C monomers are a major sector of polymer chemistry, while polymerizations of carbonyl C¼ ¼O monomers are also well established. In contrast, polymerizations involving imine C¼ ¼N monomers have received much less attention. In this review, we shall survey existing knowledge in the area of imines and azabutadienes.

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Section: 3-diazabutadienes (Azines)mentioning

confidence: 99%

“…However, BzFAz, prepared by pyrolysis of the polymer under vacuum, could be isolated as solutions, and was relatively stable for several hours. 51 In solution, BzFAz could be polymerized with cationic and anionic initiators. The structure of the polymer was dependent on the polymerization conditions.…”

Section: 3-diazabutadienes (Azines)mentioning

confidence: 99%

Synthesis and polymerizability of CN monomers

Hall

Padías

Kamachi

et al. 2012

J. Polym. Sci. A Polym. Chem.

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“…Azine compounds have attracted considerable interest in several areas: in medical and biological applications, 1,2 in the preparations of metal complexes 3,4 and in some other applications. 5,6 Over past decades, liquid crystalline and photoluminescent liquid crystalline materials have attracted remarkable attention and interest due to their major contribution to the modern technology of LCDs. Over the past three years, a wide range of liquid crystalline or photoluminescent liquid crystalline compounds with fascinating properties have been prepared.…”

Section: Introductionmentioning

confidence: 99%

Mesomorphism behaviour and photoluminescent properties of new asymmetrical 1,2-di(4-alkoxybenzylidene)hydrazines

Awad

OmarAli

Al-Karawi

et al. 2019

Journal of Chemical Research

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{1-[4-( n-Alkoxy)]-2-(4’-decyloxy)benzylidene}hydrazines ( n-alkoxy = O(CH2) nH, n = 1–9, 12, 16 or 18), an asymmetrical series of 1,2-disubstituted hydrazines, were prepared in a simple two-step procedure as a part of our continuing work in evaluating hydrophobic azine compounds as photoluminescent liquid crystalline materials. The compounds were characterized spectroscopically and their liquid crystalline behaviour and luminescent properties were evaluated using polarized light optical microscopy, differential scanning calorimetry and X-ray powder diffraction techniques. The studies revealed that all of these compounds are liquid crystalline materials exhibiting photoluminescent properties in the crystalline and liquid crystal states.

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“…Azine compounds have interesting chemical and pharmacological properties. They are attracting increased interest for their potential in medical and biological applications (2)(3)(4), the design of metal complexes (5, 6) and other material applications (7,8). In 1959, a series of azine-type liquid crystals were synthesised by Wilfrid and Glenn (9) and were found have high clearing points.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and mesomorphic properties of two series of new azine‐type liquid crystals

et al. 2008

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Synthesis and mesomorphic properties of two series of new azine-type liquid crystals, Liquid Crystals, 35:5, 581-585, Two series of symmetrical azine-type liquid crystals were synthesised and their chemical structures identified by FTIR, 1 H NMR and elemental analysis. Their mesomorphic properties were investigated by polarising optical microscopy, differential scanning calorimetry and X-ray diffraction. The characteristic of these liquid crystals is that they have a high clearing point (most were higher than 320uC) and a broad thermal range in the mesophase. The end groups of the liquid crystals had an effect on their mesomorphic properties. The series with alkoxy end groups all exhibited both smectic A (SmA) and a nematic phase, whereas the series with alkyl end groups showed only nematic phase at their lower analogues and showed both SmA and nematic properties at their higher analogues.

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Preparation and Polymerization of Benzaldehyde Formaldehyde Azine (1-Phenyl-2,3-diaza-1,3-butadiene)

Cited by 13 publications

References 24 publications

Synthesis and polymerizability of CN monomers

Synthesis and polymerizability of CN monomers

Mesomorphism behaviour and photoluminescent properties of new asymmetrical 1,2-di(4-alkoxybenzylidene)hydrazines

Synthesis and mesomorphic properties of two series of new azine‐type liquid crystals

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