Ferrocenyl-polyphenylenes: Toward Metallo-organic Polyaromatics

Roberts, Dilwyn J.; Gregg, Daniel J.; Fitchett, Christopher M.; Draper, Sylvia M.

doi:10.1021/om100862a

Cited by 14 publications

(6 citation statements)

References 35 publications

(40 reference statements)

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“…This did not improve the outcome of the attempted cyclodehydrogenation which we believe to be a consequence of the partial oxidative decomposition by Cu(II) of the exposed Fe centre in tilted ferrocenyl moieties. 6,10 Synthesis and spectroscopic characterisation of 2-ethynylferrocenyl-5,8,11,14,17-penta-tert-butylhexaperi-hexabenzocoronene (13) As a consequence of the unsuccessful cyclodehydrogenation of the ferrocene-containing 10, 11 and 12, a change of synthetic direction was required. Müllen et al 18,19 amongst others 9,20 have shown that halogen atoms incorporated into PAH are labile enough to undergo palladium catalysed coupling reactions.…”

Section: Synthesis Of Heteroatom-containing Polyphenylenes 10 11 and 12mentioning

confidence: 99%

The synthesis and characterisation of novel ferrocenyl polyphenylenes

et al. 2012

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This work describes the synthesis and characterisation of a new series of polyphenylenes with up to four ferrocenyl moieties. The synthetic route involves the preparation of a number of novel precursors. Cyclopentadienones, generated from the two-fold Knoevenagel condensation of di-ferrocenyl propanones and diketones, are used in [2 + 4] Diels-Alder cycloadditions with appropriately substituted acetylenes. 13 is amongst the compounds isolated. It is the largest ferrocenyl-supported polyaromatic hydrocarbon (PAH) to date. Prepared via a Sonogashira cross-coupling reaction between ethynyl-Fc and iodo-HBC, it comprises a hexa-peri-hexabenzocoronene (HBC) core linked via acetylene to a ferrocenyl unit (Fc). The electrochemical and absorption properties of the ferrocenyl-polyphenylenes and the fully conjugated 13 are discussed. The NLO data for 13, determined by hyper Rayleigh scattering techniques, are compared to those of similar fulleryl-based compounds in the literature.

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Section: Synthesis Of Heteroatom-containing Polyphenylenes 10 11 and 12mentioning

confidence: 99%

The synthesis and characterisation of novel ferrocenyl polyphenylenes

et al. 2012

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“…As a result, organometallic fragments assembled on substituted benzenes, polyaromatics, and heteroaromatics, such as pyridine, have attracted considerable interest as potential models for organometallic polymers [41]. Roberts et al [42] synthesized a new series of ferrocenyl-substituted polyphenylenes as one of the most important metalloorganic polyaromatics and present the successful Lewis acid-catalyzed cyclodehydrogenation of one of these to form an eight-ring fused PAH supporting a ferrocene moiety (16-ferrocenyl(tribenzo[e;g,h,i;k])perylene(6)), the largest of its kind. The failure to generate further metallo-organic superaromatics is discussed in relation to the structure of the precursors and the oxidation of the ferrocene metal center.…”

Section: Ferrocene Polymersmentioning

confidence: 99%

Organometallic Ferrocene- and Phosphorus-Containing Polymers: Synthesis and Characterization

Hussein

Asiri

2012

Designed Monomers and Polymers

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The inclusion of organometallic units into polymeric structures has attracted much attention in different fields according to the nature and behaviour of the inserted metal. Moreover, the discovery of organometallic polymers and their structural characterization initiated an explosive rebirth of organometallic chemistry. Organometallic moieties are in or pendent to the polymer backbone and examine some of the uses of the emergent metallocene polymers, and new uses are still being found for these remarkable organometallic moieties. This review gives a simple introduction to variable organometallic molecules and their characteristics. This review will focus on the syntheses and characterization of organometallic polymers, including ferrocene-and phosphorus-containing polymers. A general overview on ferrocene polymers with a special attention to ferrocene-containing liquid crystalline polymers (including a ferrocene moiety in the main chain, side-chain or dendrimers) and fullerene-ferrocene liquid crystalline polymers is presented. In addition, more details for synthesis and properties of phosphorus-containing polymers are illustrated.

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“…According to a paper from 2010, a series of ferrocenyl-substituted polyphenylenes was obtained involving tetraphenylcyclopentadienone acetylenes bearing ferrocenyl moiety and DA cycloaddition with CO extrusion ( Scheme 216 ) [ 267 ]. Moreover, [(tetraphenyl)phenyl]ferrocene, formed via the above-mentioned DA cycloaddition, underwent Lewis acid-catalyzed cyclodehydrogenation, resulting in ferrocene with an eight-ring fused PAHs-substituent [ 267 ].…”

Section: Cyclopentadienones For the Multisubstituted Benzene Ring And Naphthalene System Formationmentioning

confidence: 99%

“… DA cycloaddition with CO extrusion in synthetic route providing ferrocene derivatives bearing tetra- or pentaphenyl or eight-ring fused PAH-moieties [ 267 ]. Reagents and conditions: a = Ph 2 CO, 200 °C, 48 h; Y = up to 70%; b = next step (Scholl reaction).…”

Section: Figure and Schemesmentioning

confidence: 99%

Diels–Alder Cycloaddition with CO, CO2, SO2, or N2 Extrusion: A Powerful Tool for Material Chemistry

et al. 2021

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Phenyl, naphthyl, polyarylphenyl, coronene, and other aromatic and polyaromatic moieties primarily influence the final materials’ properties. One of the synthetic tools used to implement (hetero)aromatic moieties into final structures is Diels–Alder cycloaddition (DAC), typically combined with Scholl dehydrocondensation. Substituted 2-pyranones, 1,1-dioxothiophenes, and, especially, 1,3-cyclopentadienones are valuable substrates for [4 + 2] cycloaddition, leading to multisubstituted derivatives of benzene, naphthalene, and other aromatics. Cycloadditions of dienes can be carried out with extrusion of carbon dioxide, carbon oxide, or sulphur dioxide. When pyranones, dioxothiophenes, or cyclopentadienones and DA cycloaddition are aided with acetylenes including masked ones, conjugated or isolated diynes, or polyynes and arynes, aromatic systems are obtained. This review covers the development and the current state of knowledge regarding thermal DA cycloaddition of dienes mentioned above and dienophiles leading to (hetero)aromatics via CO, CO2, or SO2 extrusion. Particular attention was paid to the role that introduced aromatic moieties play in designing molecular structures with expected properties. Undoubtedly, the DAC variants described in this review, combined with other modern synthetic tools, constitute a convenient and efficient way of obtaining functionalized nanomaterials, continually showing the potential to impact materials sciences and new technologies in the nearest future.

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Ferrocenyl-polyphenylenes: Toward Metallo-organic Polyaromatics

Cited by 14 publications

References 35 publications

The synthesis and characterisation of novel ferrocenyl polyphenylenes

The synthesis and characterisation of novel ferrocenyl polyphenylenes

Organometallic Ferrocene- and Phosphorus-Containing Polymers: Synthesis and Characterization

Diels–Alder Cycloaddition with CO, CO2, SO2, or N2 Extrusion: A Powerful Tool for Material Chemistry

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