A New Class of Cationic Organoiron Polynorbornenes Containing Azo Dyes

Abd‐El‐Aziz, Alaa S.; Okasha, Rawda M.; Afifi, Tarek H.; Todd, Erin K.

doi:10.1002/macp.200390019

Cited by 30 publications

(14 citation statements)

References 32 publications

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“…As opposed to radical polymerization techniques, ROMP is a facile way to incorporate these units into polymers and therefore, a number of polynorbornenes with azo dyes (5) have been synthesized [48][49][50][51][52]. In Fig.…”

Section: Chemosensorsmentioning

confidence: 99%

“…A wide range of suitable monomers has been copolymerized comprising (hetero)polyaromatic compounds [15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33], and more sophisticated functionalities like conjugated oligomers [34][35][36][37][38][39], triphenylmethane [40][41][42][43][44][45][46][47], azo [48][49][50][51][52], or polymethine [53][54][55][56][57] dyes. Even transition metal coordination compounds of aluminum [58,59], iron [60], zinc [61][62][63], ruthenium [64, 65], europium …”

Section: Polymethine Dyesmentioning

confidence: 99%

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Dye-functionalized polymers via ring opening metathesis polymerization: principal routes and applications

2015

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Herein, highlights from the recent literature regarding functional dye-polymer conjugates obtained by ring opening metathesis polymerization (ROMP) are presented and the different approaches to incorporate dyes during the initiation, propagation, and termination step in ROMP are discussed. Applications in the field of chemical sensors, bioimaging, electroactive materials, self-assembly, photochromic and photoreactive materials are used to illustrate the versatility of ROMP as a technique to prepare complex functional materials. Graphical abstract

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Section: Chemosensorsmentioning

confidence: 99%

Section: Polymethine Dyesmentioning

confidence: 99%

Dye-functionalized polymers via ring opening metathesis polymerization: principal routes and applications

2015

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“…The ring opening metathesis polymerization (ROMP) of functionalized norbornene using Grubbs catalysts is a well documented process that is tolerant of a variety of functional groups 8–14. Our group has previously used Grubbs first generation catalyst to polymerize polynorbonenes with η 6 ‐arene‐η 5 ‐cyclopentadienyliron complexes in the side chain 15–18. One property of these complexes was an enhanced solubility in polar organic solvents compared to their organic counterparts.…”

Section: Introductionmentioning

confidence: 99%

Polynorbornenes Containing Ferrocene Derivatives and Alkyne‐bis(tricarbonylcobalt)

Abd‐El‐Aziz

Winram

Shipman

et al. 2010

Macromol. Rapid Commun.

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Coordination of dicobalt hexacarbonyl to the alkyne moiety of norbornene complexes containing either ferrocene or η(6) -chlorobenzene-η(5) -cyclopentadienyliron hexafluorophosphate, gave two unique trimetallic complexes available for ROMP. Polymerization of each monomer using Grubbs second generation catalyst gave organoiron/organocobalt polynorbornenes with weight average molecular weights between 55 300 and 69 000 with PDIs between 1.2 and 1.9. Cyclic voltammetric studies of the monomers and polymers at -40 °C showed a reversible reduction for cationic complexes containing η(6) -benzene-η(5) -cyclopentadienyliron and for the dicobalt hexacarbonyl moieties while, a reversible oxidation for the ferrocene containing complex was observed. Thermal analysis showed that the cobalt carbonyl moiety of the polymers degraded near 130 °C; however, the polymeric backbone was stable up to 350 °C. Scanning electron microscopy (SEM) and SEM-EDS indicated that the polymers possessed a fine globular morphology and that the distribution of iron and cobalt atoms was homogenous on the macro-scale.

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“…The intense electron withdrawing ability of the positively charged iron center facilitates nucleophilic substitution and addition reactions on the arene rings and allows for the production of these macromolecules under mild conditions. Furthermore, the iron complex demonstrates several advantages over other π-coordinated metallic moieties due to its chemical versatility, stability, low cost, and low toxicity [ 50 , 51 , 52 , 53 ].…”

Section: Introductionmentioning

confidence: 99%

Cationic Cyclopentadienyliron Complex as a Novel and Successful Nucleating Agent on the Crystallization Behavior of the Biodegradable PHB Polymer

et al. 2018

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Cationic cyclopentadienyliron (CpFe+) is one of the most fruitful organometallic moieties that has been utilized to mediate the facile synthesis of a massive number of macromolecules. However, the ability of this compound to function as a nucleating agent to improve other macromolecule properties has not been explored. This report scrutinizes the influence of the cationic complex as a novel nucleating agent on the spherulitic morphology, crystal structure, and isothermal and non-isothermal crystallization behavior of the Poly(3-hydroxybutyrate) (PHB) bacterial origin. The incorporation of the CpFe+ into the PHB materials caused a significant increase in its spherulitic numbers with a remarkable reduction in the spherulitic sizes. Unlike other nucleating agents, the SEM imageries exhibited a good dispersion without forming agglomerates of the CpFe+ moieties in the PHB matrix. Moreover, according to the FTIR analysis, the cationic organoiron complex has a strong interaction with the PHB polymeric chains via the coordination with its ester carbonyl. Yet, the XRD results revealed that this incorporation had no significant effect on the PHB crystalline structure. Though the CpFe+ had no effect on the polymer’s crystal structure, it accelerated outstandingly the melt crystallization of the PHB. Meanwhile, the crystallization half-times (t0.5) of the PHB decreased dramatically with the addition of the CpFe+. The isothermal and non-isothermal crystallization processes were successfully described using the Avrami model and a modified Avrami model, as well as a combination of the Avrami and Ozawa methods. Finally, the effective activation energy of the PHB/CpFe+ nanocomposites was much lower than those of their pure counterparts, which supported the heterogeneous nucleation mechanism with the organometallic moieties, indicating that the CpFe+ is a superior nucleating agent for this class of polymer.

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A New Class of Cationic Organoiron Polynorbornenes Containing Azo Dyes

Cited by 30 publications

References 32 publications

Dye-functionalized polymers via ring opening metathesis polymerization: principal routes and applications

Dye-functionalized polymers via ring opening metathesis polymerization: principal routes and applications

Polynorbornenes Containing Ferrocene Derivatives and Alkyne‐bis(tricarbonylcobalt)

Cationic Cyclopentadienyliron Complex as a Novel and Successful Nucleating Agent on the Crystallization Behavior of the Biodegradable PHB Polymer

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