Synthesis, characterization and polymerization of the novel carbazole-based monomer 9-(bicyclo[2.2.1]hept-5-en-2-ylmethyl)-9H-carbazole

Mustonen, Ilpo; Hukka, Terttu I.; Pakkanen, Tuula T.

doi:10.1002/1521-3927(20001201)21:18<1286::aid-marc1286>3.0.co;2-9

Cited by 23 publications

(19 citation statements)

References 8 publications

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“…The BHMCZ monomer was synthesized according to the instructions given in reference [7]. Other chemicals were obtained from commercial sources.…”

Section: Methodsmentioning

confidence: 99%

“…[7,8] All operations were carried out under an inert atmosphere using a glove box and nitrogen and vacuum line techniques. Copolymerization was carried out at an ethylene overpressure of 0.5 atm and at 60 8C in a 500 ml stainless steel reactor system equipped with a stirrer.…”

Section: Polymerizationmentioning

confidence: 99%

“…The comonomer was a mixture of the endo and exo isomers in a ratio of 65:35. [7] The terms endo and exo are used to describe the orientation of the methylcarbazole group (-CH 2 -R) with respect to the bridge of the norbornene group. In this study the resonance assignments of the endo and exo isomers of the carbazole-functionalized comonomer were completed by 1D 13 C DEPT NMR and 2D 1 H-1 H COSYand 1 H-13 C HXCO NMR analysis.…”

Section: Structural Characterization Of Bhmcz Comonomermentioning

confidence: 99%

“…The glass transition temperature of this novel poly(ethylene-co-BHMCZ) copolymer was earlier found to be below room temperature. [7] Experimental Part…”

Section: Introductionmentioning

confidence: 99%

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NMR Characterization of Carbazole‐Substituted Norbornene Comonomer 9‐(Bicyclo[2.2.1.]hept‐5‐en‐2‐ylmethyl)‐9H‐carbazole (BHMCZ) and Poly(ethylene‐co‐BHMCZ) Copolymer

Mustonen

Hukka

Pakkanen

2003

Macro Chemistry & Physics

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Carbazole‐substituted norbornene comonomer 9‐(bicyclo[2.2.1.]hept‐5‐en‐2‐ylmethyl)‐9H‐carbazole (BHMCZ) can be copolymerized with ethylene using the [Ph2C(Ind)(Cp)ZrCl2] catalyst and methylaluminoxane (MAO) cocatalyst system. The microstructures of BHMCZ comonomer and of ethylene–BHMCZ copolymer containing 4.6 mol‐% BHMCZ units in the chain were characterized by one‐dimensional 13C DEPT and two‐dimensional homonuclear 1H‐1H COSY and heteronuclear 1H‐13C HXCO NMR spectroscopy. The BHMCZ comonomer appears as endo and exo stereoisomers, which were identified on the basis of chemical shifts, signal multiplicities, and coupling in the 2D NMR spectra. The NMR information on the BHMCZ isomers was used to assist in the determination of the chemical shifts and microstructure of ethylene–BHMCZ copolymer. The NMR analysis of ethylene–BHMCZ copolymer indicated that exo‐BHMCZ polymerizes with ethylene slightly more readily than does endo‐BHMCZ under the polymerization conditions employed.

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“…The BHMCZ monomer was synthesized according to the instructions given in reference [7]. Other chemicals were obtained from commercial sources.…”

Section: Methodsmentioning

confidence: 99%

Section: Polymerizationmentioning

confidence: 99%

Section: Structural Characterization Of Bhmcz Comonomermentioning

confidence: 99%

“…The glass transition temperature of this novel poly(ethylene-co-BHMCZ) copolymer was earlier found to be below room temperature. [7] Experimental Part…”

Section: Introductionmentioning

confidence: 99%

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NMR Characterization of Carbazole‐Substituted Norbornene Comonomer 9‐(Bicyclo[2.2.1.]hept‐5‐en‐2‐ylmethyl)‐9H‐carbazole (BHMCZ) and Poly(ethylene‐co‐BHMCZ) Copolymer

Mustonen

Hukka

Pakkanen

2003

Macro Chemistry & Physics

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“…Carbazole also can be easily functionalized at the (3,6)-, [38][39][40] (2,7)-, 41 or N-positions [42][43][44] and then covalently linked into polymeric systems, both in the main chain [45][46][47][48][49][50] as building blocks and in the side chain as pendent groups. [51][52][53][54][55] It is thus worthwhile to design a carbazole-based aromatic dicarboxylic acid as a starting monomer for the preparation of a new class of high-performance polyarylates with novel optoelectronic functions.…”

mentioning

confidence: 99%

Synthesis and Photoluminescence of Novel Organo-Soluble Polyarylates Bearing (N-Carbazolyl)triphenylamine Moieties

Liou¹,

Hsiao²,

Huang³

et al. 2007

Polym J

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ABSTRACT:A new series of polyarylates containing carbazolyl-substituted triphenylamine units were synthesized by direct polycondensation of 4,4 0 -dicarboxy-4 00 -N-carbazolyltriphenylamine with various bisphenols. All polymers were highly soluble in various common organic solvents and could afford tough, transparent, and colorless films by solution casting. These amorphous and organo-soluble polyarylates showed no significant decomposition below 470 C in both nitrogen and air atmospheres with glass transition temperatures (T g ) ranging from 234 to 287 C. In THF solution, these polyarylates exhibited blue photoluminescence around 464-476 nm with quantum yield up to 28%. The photoluminescence exhibited solvent effect and was red-shifted in the polar solvent at room temperature.

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The effect of TIBA on metallocene/MAO catalyzed synthesis of propylene oxazoline copolymers and their use in reactive blending

Kaya

Pompe

Schulze

et al. 2002

J of Applied Polymer Sci

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Oxazoline-functionalized polypropylenes were synthesized by using the rac-Et[1-Ind] 2 ZrCl 2 /MAO catalyst system. The used comonomers were 2-(9-decene-1-yl)-1,3-oxazoline (R-Ox1), 2-(9-decene-1-yl)-4,4-dimethyl-1,3-oxazoline (R-Ox2), and 2-(4-(10-undecene-1-oxy)phenyl)-1,3-oxazoline (R-Ox3). The oxazolines reduce the catalyst activity in the order R-Ox3 Ͼ R-Ox1 Ͼ R-Ox2. By the addition of triisobutylaluminum (TIBA), the catalyst poisoning is reduced and is most pronounced in the R-Ox1-and R-Ox2-containing systems. The oxazoline-containing copolymers were melt blended with carboxylic acid end-functionalized polystyrene (PS-COOH) at 200°C. Strong changes in the morphology of the reactive blends compared to the nonreactive blends, especially the cocontinuous morphology in a poly(propylene-co-R-Ox3)/PS-COOH blend, indicate the usefulness of the modified copolymers in the reactive blending processes.

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Synthesis, characterization and polymerization of the novel carbazole-based monomer 9-(bicyclo[2.2.1]hept-5-en-2-ylmethyl)-9H-carbazole

Cited by 23 publications

References 8 publications

NMR Characterization of Carbazole‐Substituted Norbornene Comonomer 9‐(Bicyclo[2.2.1.]hept‐5‐en‐2‐ylmethyl)‐9H‐carbazole (BHMCZ) and Poly(ethylene‐co‐BHMCZ) Copolymer

NMR Characterization of Carbazole‐Substituted Norbornene Comonomer 9‐(Bicyclo[2.2.1.]hept‐5‐en‐2‐ylmethyl)‐9H‐carbazole (BHMCZ) and Poly(ethylene‐co‐BHMCZ) Copolymer

Synthesis and Photoluminescence of Novel Organo-Soluble Polyarylates Bearing (N-Carbazolyl)triphenylamine Moieties

The effect of TIBA on metallocene/MAO catalyzed synthesis of propylene oxazoline copolymers and their use in reactive blending

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