Polymerizability of asymmetric azines bearing bicyclic substituents

Tsuchiya, Atsuki; Hashidzume, Akihito; Harada, Akira; Kamachi, Mikiharu

doi:10.1163/156855504774076299

Cited by 7 publications

(3 citation statements)

References 27 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%

“…53 The polymerizability of these asymmetric azines and others, that is, formaldehyde (1R)-(þ)-nopinone azine (FNpAz) and formaldehyde norcamphor azine (FNcAz), was investigated. 52 The polymerizability of these asymmetric azines depended on the bulkiness of the bicyclic moiety. Most bulky azines, that is, CFAz and FFAz, showed poor polymerizability presumably because of steric hindrance.…”

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%

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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“…The synthesis of organic−inorganic materials is a growing field of research. The primary purpose of designing these new structural types is to combine the functional properties of organic and inorganic structures to create compounds with new device applications. − In general, common techniques used to design these hybrid structures include the “brick and mortar” approach and the use of templating agents. Our interest has been in the design and synthesis of novel extended lattice systems based on organoammonium metal halide salts.…”

Section: Introductionmentioning

confidence: 99%

Novel Series of Ribbon Structures in Dialkylammonium Chlorocadmates Obtained By Dimensional Reduction of the Hexagonal CdCl₂ Lattice

Thorn

Willett

Twamley

2006

Crystal Growth & Design

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Table S2. Bond lengths [Å] and angles [°] for the structure of α -[DEA][Cd 2 Cl 5 (H 2 O)]. Atoms Distance Atoms Angle Atoms Angle Cd(1)-Cl(3) 2.500(2) Cd(1)-Cl(1) 2.571(2) Cd(1)-Cl(4) 2.601(2) Cd(1)-Cl(5)#1 2.636(2) Cd(1)-Cl(2) 2.685(2) Cd(1)-Cl(5) 2.804(2) Cd(2)-Cl(1)#3 2.519(2) Cd(2)-Cl(4) 2.574(2) Cd(2)-Cl(2)#1 2.663(2) Cd(2)-Cl(5) 2.666(2) Cd(2)-Cl(2)#3 2.679(2) O(1)-Cd(2) 2.352(5) Cl(3)-Cd(1)-Cl(1) 97.29(6) Cl(3)-Cd(1)-Cl(4) 92.87(5) Cl(1)-Cd(1)-Cl(4) 98.83(6) Cl(3)-Cd(1)-Cl(5)#1 167.36(6) Cl(1)-Cd(1)-Cl(5)#1 95.19(6) Cl(4)-Cd(1)-Cl(5)#1 87.21(5) Cl(3)-Cd(1)-Cl(2) 94.68(5) Cl(1)-Cd(1)-Cl(2) 85.70(6) Cl(4)-Cd(1)-Cl(2) 170.64(5) Cl(5)#1-Cd(1)-Cl(2) 84.22(5) Cl(3)-Cd(1)-Cl(5) 87.55(5) Cl(1)-Cd(1)-Cl(5) 173.05(5) Cl(4)-Cd(1)-Cl(5) 85.87(5) Cl(5)#1-Cd(1)-Cl(5) 79.85(5) Cl(2)-Cd(1)-Cl(5) 88.93(5) Cd(2)#2-Cl(1)-Cd(1) 96.90(6) Cd(2)-O(1)-H(1) 101.0 Cd(2)-O(1)-H(2) 98.6 O(1)-Cd(2)-Cl(1)#3 99.78(1) O(1)-Cd(2)-Cl(4) 91.50(1)Cl( 1)#3-Cd(2)-Cl(4) 93.74( 6)Cl( 1)#3-Cd(2)-Cl(2)#1 96.53( 5)Cl( 4)-Cd(2)-Cl(2)#1 91.94( 5)O( 1)-Cd(2)-Cl( 5) 79.40( 1)Cl( 1)#3-Cd(2)-Cl( 5) 176.84( 6)Cl( 4)-Cd(2)-Cl( 5) 89.34( 6)Cl( 2)#1-Cd(2)-Cl( 5) 84.08( 5)Cl( 1)#3-Cd(2)-Cl(2)#3 86.86(6) Cl(4)-Cd(2)-Cl(2)#3 177.37(5) Cl(2)#1-Cd(2)-Cl(2)#3 85.45(5) Cl(5)-Cd(2)-Cl(2)#3 90.10(5) Cd(2)#1-Cl(2)-Cd(2)#2 94.55(5) Cd(2)#1-Cl(2)-Cd(1) 95.31(5) Cd(2)#2-Cl(2)-Cd(1) 90.51(5) Cd(2)-Cl(4)-Cd(1) 95.03(6) Cd(1)#1-Cl(5)-Cd(2) 96.40(5) Cd(1)#1-Cl(5)-Cd(1) 100.15(5) Cd(2)-Cl(5)-Cd(1) 88.47(5) Symmetry transformations used to generate equivalent atoms: #1 -x+1, -y+1, -z+1; #2 x, y-1, z; #3 x, y+1, zTable S4. Bond lengths [Å] and angles [°] for the structure of β -[DEA][Cd 2 Cl 5 (H 2 O)]. Atoms Distance Atoms Angle Atoms Angle Cd(1)-Cl(4)#1 2.544(1) Cd(1)-Cl(1) 2.581(1) Cd(1)-Cl(2) 2.629(1) Cd(1)-Cl(5)#1 2.675(1) Cd(1)-Cl(2)#2 2.686(1) Cd(1)-O(1) 2.298(4) Cd(2)-Cl(1) 2.589(1) Cd(2)-Cl(3) 2.514(1) Cd(2)-Cl(4) 2.591(2) Cd(2)-Cl(2) 2.676(1) Cd(2)-Cl(5)#3 2.682(1) Cd(2)-Cl(5) 2.687(1) O(1)-Cd(1)-Cl(4)#1 90.40(1) O(1)-Cd(1)-Cl(1) 98.19(1) Cl(4)#1-Cd(1)-Cl(1) 94.77(4) O(1)-Cd(1)-Cl(2) 90.01(1) Cl(4)#1-Cd(1)-Cl(2) 178.32(5) Cl(1)-Cd(1)-Cl(2) 86.78(4) O(1)-Cd(1)-Cl(5)#1 84.53(1)Cl( 4)#1-Cd(1)-Cl( 5)#1 89.37( 4)Cl( 1)-Cd(1)-Cl( 5)#1 175.01( 4)Cl( 4)#1-Cd(1)-Cl(2)#2 93.65( 4)Cl( 1)-Cd(1)-Cl(2)#2 93.84(4) Cl(2)-Cd(1)-Cl(2)#2 85.60(4) Cl(5)#1-Cd(1)-Cl(2)#2 83.11(4) Cd(1)-Cl(1)-Cd(2) 95.29(4) Cd(1)-O(1)-H(1) 113.9 Cd(1)-O(1)-H(2) 126.0 Cl(3)-Cd(2)-Cl(1) 100.88(4) Cl(3)-Cd(2)-Cl(4) 93.67(4) Cl(1)-Cd(2)-Cl(4) 93.65(4) Cl(3)-Cd(2)-Cl(2) 93.65(4) Cl(1)-Cd(2)-Cl(2) 85.65(4) Cl(4)-Cd(2)-Cl(2) 172.65(4) Cl(3)-Cd(2)-Cl(5)#3 170.09(4) Cl(1)-Cd(2)-Cl(5)#3 88.27(4) Cl(4)-Cd(2)-Cl(5)#3 89.50(4) Cl(2)-Cd(2)-Cl(5)#3 83.17(4) Cl(3)-Cd(2)-Cl(5) 88.55(4) Cl(1)-Cd(2)-Cl(5) 170.26(4) Cl(4)-Cd(2)-Cl(5) 88.14(4) Cl(2)-Cd(2)-Cl(5) 91.36(4) Cl(5)#3-Cd(2)-Cl(5) 82.17(4) Cd(1)-Cl(2)-Cd(2) 92.14(4) Cd(1)-Cl(2)-Cd(1)#2 94.40(4) Cd(2)-Cl(2)-Cd(1)#2 96.72(4) Cd(1)#4-Cl(4)-Cd(2) 93.31(4) Cd(1)#4-Cl(5)-Cd(2)#3 96.83(4) Cd(1)#4-Cl(5)-Cd(2) 88.29(4) Cd(2)#3-Cl(5)-Cd(2) 97.83(4) Symmetry transformations used...

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A dual strategy for synthesizing carbon/defect comodified polymeric carbon nitride porous nanotubes with boosted photocatalytic hydrogen evolution and synchronous contaminant degradation

Huo

Deng

et al. 2021

Applied Catalysis B: Environmental

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Polymerizability of asymmetric azines bearing bicyclic substituents

Cited by 7 publications

References 27 publications

Synthesis and polymerizability of CN monomers

Synthesis and polymerizability of CN monomers

Novel Series of Ribbon Structures in Dialkylammonium Chlorocadmates Obtained By Dimensional Reduction of the Hexagonal CdCl₂ Lattice

A dual strategy for synthesizing carbon/defect comodified polymeric carbon nitride porous nanotubes with boosted photocatalytic hydrogen evolution and synchronous contaminant degradation

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Polymerizability of asymmetric azines bearing bicyclic substituents

Cited by 7 publications

References 27 publications

Synthesis and polymerizability of CN monomers

Synthesis and polymerizability of CN monomers

Novel Series of Ribbon Structures in Dialkylammonium Chlorocadmates Obtained By Dimensional Reduction of the Hexagonal CdCl2 Lattice

A dual strategy for synthesizing carbon/defect comodified polymeric carbon nitride porous nanotubes with boosted photocatalytic hydrogen evolution and synchronous contaminant degradation

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Novel Series of Ribbon Structures in Dialkylammonium Chlorocadmates Obtained By Dimensional Reduction of the Hexagonal CdCl₂ Lattice