Synthesis and characterization of photoconductive C60–N-vinylcarbazole copolymers

A series of polyferrocenylsilane (PFS) random copolymers containing covalently bound pendant [C60]fullerene groups, the first well‐characterized metallopolymers with pendant C60 units, have been prepared and characterized. The fullerene content of the prepared copolymers ranges from 7 to 24% relative to monomer unit. The desired copolymers were synthesized in three steps: metal‐catalyzed ring opening polymerization of sila[1]ferrocenophanes was performed to synthesize random copolymers of poly(ferrocenylmethylphenylsilane‐co‐ferrocenylchloromethylsilane); the resulting random PFSs were then functionalized by reaction with 11‐azido‐1‐undecanol to give PFSs with pendant azide groups; the desired donor–acceptor C60‐containing PFSs were then synthesized by the reaction of the azide group in the side chains with C60 in toluene at 110 °C. The resulting C60‐containing PFSs are air‐stable and soluble in aromatic solvents, chloroform, or THF. The UV‐vis spectra of these materials show broad absorption up to 800 nm. Thin films of these materials were examined as the active layer in rare examples of all solid‐state sandwich‐type diode devices based on ferrocene‐fullerene dyads. The devices exhibit photoconducting and photovoltaic responses, with an open circuit potential of ca. 0.3 V under white light illumination.

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“…In the 13 C NMR spectrum, a very broad signal was observed ranging from 80 to 180 ppm, which is assigned to the attached C 60 moiety. [50] 2…”

Section: Characterization Of C 60 -Containing Pfsmentioning

confidence: 99%

Donor–Acceptor C₆₀‐Containing Polyferrocenylsilanes: Synthesis, Characterization, and Applications in Photodiode Devices

Nanjo

Cyr

Liu

et al. 2008

Adv Funct Materials

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“…The outcomes of the copolymerization reaction with the mixture of N -vinylcarbazole and small carbon nanoparticles suggest that the nanoparticles are capable of the same behavior found and established for fullerenes with respect to their similar copolymerization with vinyl monomers. − For example, C 60 could be copolymerized with styrene and methyl methacrylate in radical polymerization reactions (thermally initiated or with a radical initiator), yielding copolymers with fullerene cages incorporated in the polymer structure. ,, Here for comparison, C 60 was copolymerized with N -vinylcarbazole in the thermally initiated polymerization under reaction conditions similar to those for styrene–C 60 copolymers reported in the literature . The outcomes on the formation of copolymers in which C 60 cages are incorporated in the PVK polymer structure (denoted as PVK–C 60 ) were similar to those for copolymers of C 60 with polystyrene and poly(methyl methacrylate) (PMMA), including optical properties of the copolymers. ,, …”

Section: Resultsmentioning

confidence: 83%

“…As compared in the presentation above, both C 60 cages and the small carbon nanoparticles can participate in radical polymerization reactions with vinyl molecules. For the PVK–C 60 , the mode of such participation must be the radical addition to the fullerene cage, the same as what is known in similarly synthesized styrene–C 60 and PMMA–C 60 copolymers. − A similar radical reaction on the carbon nanoparticle surface is likely in the formation of the PVK–CDots, in which there are probably additional surface passivation effects provided by the noncovalent interactions with the carbazole moieties (Figure ). The effectiveness of the carbon nanoparticle surface passivation in the PVK–CDots is reflected by the high fluorescence performance of the sample, which serves as an interesting example of potentially far-reaching implications with respect to alternative surface passivation schemes that adhere to the general definition on CDots but different from what have been studied in various preparations of CDots. , …”

Section: Resultsmentioning

confidence: 88%

Zero-Dimensional Carbon Allotropes—Carbon Nanoparticles Versus Fullerenes in Functionalization by Electronic Polymers for Different Optical and Redox Properties

et al. 2018

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Fullerene cages are known as being able to participate in radical initiated copolymerization reactions with vinyl monomers for polymer-functionalized fullerenes. In this work, poly( N -vinylcarbazole) (PVK) was selected as a representative of electronic polymers in the functionalization of fullerene C 60 by the same copolymerization reaction to yield the PVK–C 60 . Similarly found was that small carbon nanoparticles could also participate in the same copolymerization reaction for the nanoparticles to be surface-functionalized and -passivated by the attached PVK polymers, which are structurally adhering to the general definition on carbon dots (CDots), thus PVK–CDots. In the comparison between PVK–CDots and PVK–C 60 , the former was found to be more absorptive and therefore more effective in photon harvesting across the visible spectral region and also brightly fluorescent, orders of magnitude more so than the latter. Similar to the PVK–C 60 and C 60 cages in general, the PVK–CDots exhibited significant photoinduced electron accepting characteristics and, at the same time, also extraordinary electron donating abilities that are not available to fullerenes. Because fullerene-based composites with electronic polymers including PVK have found significant applications in optoelectronic devices and systems, the prospect of CDots represented by the PVK–CDots for similar purposes is discussed.

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“…Because of the wide range of interesting features of the C 60 molecule, many C 60 polymeric derivatives have been prepared in recent years [9][10][11] . Methodologies used range from free-radical 12 , anionic 13 or step-growth 14 polymerization. In addition, functionalized C 60 can be copolymerized with other monomers 15 or grafted onto polymers 16 .…”

Section: Introductionmentioning

confidence: 99%

Fabrication of [60] Fullerene Grafted Polymer: Self-Assembly Behavior in Polar Solvents

Haldorai¹,

Islam²,

Shim³

2014

Asian J. Chem.

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In this report, we prepared a new type of [60] fullerene grafted poly(2-bromomethyl)acrylic acid. First step was the free-radical polymerization of 2-(bromomethyl)acrylic acid by using 2,2'-azobisisobutyronitrile. Then a nucleophilic substitution reaction was performed to substitute the bromine atoms present in the polymer with azide groups. Finally, the C60 grafted polymer was prepared by the reaction of azido functionalized polymer with C60. Results of Fourier transform infrared spectroscopy and ultraviolet-visible spectroscopy indicated that the C60 was chemically bonded to the polymer. The aggregation behavior of the resulting polymer in polar solvents was studied by transmission electron microscopy. The resultant polymer retained both electronic property of the C60 moiety and processability property of the polymer.

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Synthesis and characterization of photoconductive C60–N-vinylcarbazole copolymers

Cited by 19 publications

References 39 publications

Donor–Acceptor C₆₀‐Containing Polyferrocenylsilanes: Synthesis, Characterization, and Applications in Photodiode Devices

Donor–Acceptor C₆₀‐Containing Polyferrocenylsilanes: Synthesis, Characterization, and Applications in Photodiode Devices

Zero-Dimensional Carbon Allotropes—Carbon Nanoparticles Versus Fullerenes in Functionalization by Electronic Polymers for Different Optical and Redox Properties

Fabrication of [60] Fullerene Grafted Polymer: Self-Assembly Behavior in Polar Solvents

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Synthesis and characterization of photoconductive C60–N-vinylcarbazole copolymers

Cited by 19 publications

References 39 publications

Donor–Acceptor C60‐Containing Polyferrocenylsilanes: Synthesis, Characterization, and Applications in Photodiode Devices

Donor–Acceptor C60‐Containing Polyferrocenylsilanes: Synthesis, Characterization, and Applications in Photodiode Devices

Zero-Dimensional Carbon Allotropes—Carbon Nanoparticles Versus Fullerenes in Functionalization by Electronic Polymers for Different Optical and Redox Properties

Fabrication of [60] Fullerene Grafted Polymer: Self-Assembly Behavior in Polar Solvents

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Donor–Acceptor C₆₀‐Containing Polyferrocenylsilanes: Synthesis, Characterization, and Applications in Photodiode Devices

Donor–Acceptor C₆₀‐Containing Polyferrocenylsilanes: Synthesis, Characterization, and Applications in Photodiode Devices