Selective dispersion of single-walled carbon nanotubes via easily accessible conjugated click polymers

Gerstel, Peter; Klumpp, Stefanie; Hennrich, Frank; Altintas, Ozcan; Eaton, Thomas R.; Mayor, Marcel; Barner‐Kowollik, Christopher; Kappes, Manfred M.

doi:10.1039/c2py20161e

Cited by 29 publications

(26 citation statements)

References 53 publications

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“…A large excess of 1,8-dibromooctane was used to prevent two-fold reaction on one alkyl chain and potassium carbonate was found to give better yields than sodium hydroxide 16 or sodium hydride (in ethanol). 19 However, besides the desired reaction, halogen exchange also occurred, leading to fluorinated alkyl side chains (Fig. The alkyne entities on compound 4 were then introduced via a Sonogashira reaction with trimethylsilylacetylene (TMSA) in the presence of triethylamine.…”

Section: Resultsmentioning

confidence: 99%

“…18 From 1 H NMR analysis it was observed that some of the bromine atoms on the alkyl side chains were replaced by iodine during this reaction, leading to an extra triplet at 3.18 ppm (Fig. The azide functionalities were introduced to precursor 3 in a highly efficient manner (96% yield) using the same reaction conditions as those applied for compound 4, and the Sonogashira reaction on 2,5-diiodobenzene derivative 7 was conducted in the same way as that mentioned above, in this case with TBAF as the deprotection agent, 19 yielding 2,5-diethynylbenzene monomer 9 in 72% yield. The amount of iodinated product depends on the amount of co-catalyst causing the halogenhalogen exchange.…”

Section: Resultsmentioning

confidence: 99%

“…1 1,4-Bis(8-bromooctyloxy)-2,5-diethynylbenzene (4). Modified procedure: 19 1,4-diiodo-2,5-bis(octyloxy)benzene (7) (1.00 g, 1.70 mmol) was dissolved in dry THF/Et 3 N (1/1, 6 mL). After purging the solution with nitrogen for 10 min, CuI (25.7 mg, 5 mol%), PdCl 2 (PPh 3 ) 2 (94.4 mg, 5 mol%) and trimethylsilylacetylene (0.554 g, 5.64 mmol) were added, and the mixture was stirred overnight at 40°C under an inert atmosphere.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of a multifunctional poly(p-phenylene ethynylene) scaffold with clickable azide-containing side chains for (bio)sensor applications

et al. 2015

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Poly(p-phenylene ethynylene) (PPE) copolymers with alternating alkoxy and azide-functionalized alkoxy side chains were efficiently synthesized via Sonogashira polymerization and the materials were fully characterized. Among the different synthetic protocols investigated, the best results were obtained when employing a pre-polymerization functionalization approach and upon implementing the azide-functionalized side chains on the diiodophenyl building block. End-capping of the conjugated polymer chains is shown to be essential for preventing side reactions. As a proof of principle, phenylacetylene is clicked in a nearly quantitative way on the polymer backbone. Furthermore, successful click-immobilization of randomly alkynylated protein A onto an azide-functionalized PPE film illustrates the potential use of these materials in a variety of (bio)sensor applications. † Electronic supplementary information (ESI) available: MALDI-TOF mass spectrum of copolymer P2a, 1 H and 13 C NMR spectra of monomers and polymers, cyclic voltammograms, and FT-IR spectra. See

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Synthesis of a multifunctional poly(p-phenylene ethynylene) scaffold with clickable azide-containing side chains for (bio)sensor applications

et al. 2015

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“…(8,6) tubes. [80] These discoveries open up the possibility to use polymer-functionalized SWNTs as efficient absorbers and charge transfer hybrid materials for application in, among others, photovoltaics. This will be discussed in more detail in Section 4.…”

Section: Introductionmentioning

confidence: 99%

Functional Single‐Walled Carbon Nanotubes and Nanoengineered Networks for Organic‐ and Perovskite‐Solar‐Cell Applications

Barbero

Stranks

2016

Advanced Materials

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Carbon nanotubes have a variety of remarkable electronic and mechanical properties that, in principle, lend them to promising optoelectronic applications. However, the field has been plagued by heterogeneity in the distributions of synthesized tubes and uncontrolled bundling, both of which have prevented nanotubes from reaching their full potential. Here, a variety of recently demonstrated solution-processing avenues is presented, which may combat these challenges through manipulation of nanoscale structures. Recent advances in polymer-wrapping of single-walled carbon nanotubes (SWNTs) are shown, along with how the resulting nanostructures can selectively disperse tubes while also exploiting the favorable properties of the polymer, such as light-harvesting ability. New methods to controllably form nanoengineered SWNT networks with controlled nanotube placement are discussed. These nanoengineered networks decrease bundling, lower the percolation threshold, and enable a strong enhancement in charge conductivity compared to random networks, making them potentially attractive for optoelectronic applications. Finally, SWNT applications, to date, in organic and perovskite photovoltaics are reviewed, and insights as to how the aforementioned recent advancements can lead to improved device performance provided.

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“…CuAAC is thus the most important reaction in “click chemistry” [ 4 – 7 ]. A number of studies have been published on CuAAC, which is applied in a wide range of fields from bio-related chemistry [ 8 – 12 ] to materials science [ 13 – 29 ], as well as polymer synthesis [ 30 – 36 ]. Most of these studies deal with the 1,2,3-triazole moiety just as a linker.…”

Section: Introductionmentioning

confidence: 99%

Quarternization of 3-azido-1-propyne oligomers obtained by copper(I)-catalyzed azide–alkyne cycloaddition polymerization

Nakano¹,

Hashidzume²,

Sato³

2015

Beilstein J. Org. Chem.

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Selective dispersion of single-walled carbon nanotubes via easily accessible conjugated click polymers

Cited by 29 publications

References 53 publications

Synthesis of a multifunctional poly(p-phenylene ethynylene) scaffold with clickable azide-containing side chains for (bio)sensor applications

Synthesis of a multifunctional poly(p-phenylene ethynylene) scaffold with clickable azide-containing side chains for (bio)sensor applications

Functional Single‐Walled Carbon Nanotubes and Nanoengineered Networks for Organic‐ and Perovskite‐Solar‐Cell Applications

Quarternization of 3-azido-1-propyne oligomers obtained by copper(I)-catalyzed azide–alkyne cycloaddition polymerization

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