Synthesis of substituted norbornenes and their polymerization to polynorbornenes with flexible aliphatic side-chains

Abd‐El‐Aziz, Alaa S.; May, Leslie J.; Edel, Andrea L.

doi:10.1002/1521-3927(20000601)21:9<598::aid-marc598>3.0.co;2-0

Cited by 23 publications

(13 citation statements)

References 13 publications

(27 reference statements)

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“…Our research has focused on the synthesis of monomeric and polymeric materials containing arenes coordinated to cationic cyclopentadienyliron moieties in their backbones or side chains 21, 24–26, 30–35. Recently, we synthesized thermally stable polynorbornene with pendant ether linkages 36–38. This article describes the synthetic strategies and structural characterization of a series of organoiron monomeric and polymeric materials.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of norbornenes containing cationic mono‐ and di(cyclopentadienyliron)arene complexes and their ring‐opening metathesis polymerization

Abd‐El‐Aziz

Okasha

May

et al. 2006

J. Polym. Sci. A Polym. Chem.

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A number of classes of polynorbornenes containing cationic iron moieties within their side chains were prepared via ring-opening metathesis polymerization with a ruthenium-based catalyst. The iron-containing polymers displayed excellent solubility in polar organic solvents. The weight-average molecular weights of these polymeric materials were estimated to be in the range of 18,000-48,000. Thermogravimetric analysis of these polymers showed two distinct weight losses. The first weight loss was in the range of 204-260 8C and was due to the loss of the metallic moieties, whereas the second weight loss was observed at 368-512 8C and was due to the degradation of the polymer backbone. Cyclic voltammetry studies of the iron-containing polymers showed that the 18 e À cationic iron centers underwent a reduction to give the neutral 19 e À complexes at half-wave potential (E 1/2 ) ¼ À1.105 V. Photolysis of the metallated polymers led to the isolation of the norbornene polymers in very good yields. Differential scanning calorimetry studies showed a sharp increase in the glass-transition temperatures up to 91 8C when rigid aromatic side chains were incorporated into the norbornene polymers.

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Section: Introductionmentioning

confidence: 99%

Synthesis of norbornenes containing cationic mono‐ and di(cyclopentadienyliron)arene complexes and their ring‐opening metathesis polymerization

Abd‐El‐Aziz

Okasha

May

et al. 2006

J. Polym. Sci. A Polym. Chem.

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“…[46,47] As an example, Scheme 9 shows one of the strategies utilized to prepare this class of organometallic polymer. Ruthenium dichloroarene complex 21 was reacted with the bimetallic iron complex containing terminal phenolic groups (33) to produce the mixed metal polymer 34. The molecular weight of polymer 34 was approximately 19 000.…”

Section: Methodsmentioning

confidence: 99%

“…[33][34][35][36] While some of these organometallic monomers were polymerized via ROMP of the norbornene units, others were demetallated prior to polymerization.…”

Section: Ring-opening Metathesis Polymerization (Romp) Of Substitutedmentioning

confidence: 99%

Organometallic Polymers of the Transition Metals

Abd‐El‐Aziz

2002

Macromol. Rapid Commun.

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164

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This article provides a comprehensive review of the synthesis, properties and applications of organometallic polymers of the transition metals. The different classes of organometallic polymers are described according to their structural make‐up, as well as by their methods of synthesis. A number of examples of each class are given to emphasize the richness and diversity in these areas of research. In addition to linear polymers, hyperbranched, crosslinked, star and dendritic polymers are also described. The properties that transition metal‐containing organometallic polymers possess, as well as the applications that these materials have found in various domains are highlighted. magnified image

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“…These signals were assigned on the basis of the typical values of double-bond chemical shifts of substituted norbornenes. [9][10][11] As can be seen in the 1 H-1 H COSY NMR spectrum in Figure 1, protons H-5 and H-6 are strongly coupled to each other (J H-5, H-6 ¼ 5.7 Hz) causing a cross peak (a). Protons H-6 and H-5 are also coupled to their nearest neighboring protons H-1 (b) and H-4 (c), respectively.…”

Section: Structural Characterization Of Bhmcz Comonomermentioning

confidence: 99%

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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Synthesis of substituted norbornenes and their polymerization to polynorbornenes with flexible aliphatic side-chains

Cited by 23 publications

References 13 publications

Synthesis of norbornenes containing cationic mono‐ and di(cyclopentadienyliron)arene complexes and their ring‐opening metathesis polymerization

Synthesis of norbornenes containing cationic mono‐ and di(cyclopentadienyliron)arene complexes and their ring‐opening metathesis polymerization

Organometallic Polymers of the Transition Metals

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

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