Light-induced Electron Transfer on the Single Wall Carbon Nanotube Surrounded in Anthracene Dendron in Aqueous Solution

Sandanayaka, Atula S. D.; Takaguchi, Yutaka; Uchida, Tetsuya; Sako, Yuuki; Morimoto, Yu; Araki, Yasuyuki; Ito, Osamu

doi:10.1246/cl.2006.1188

Cited by 35 publications

(30 citation statements)

References 7 publications

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“…Fluorescence quenching studies of SWNT-anthracene adducts have been reported. [9][10][11] In Table IV the binding energies of a number of pyrene derivatives are presented. As expected, due to the larger footprint of pyrene the binding energy E B is higher than for that of anthracene.…”

Section: Resultsmentioning

confidence: 99%

“…By contrast, supramolecular (non-covalent) functionalization via π -π stacking has only a minimal effect on their electronic properties. [4][5][6][7] In this context, a range of polycyclic aromatics have been studied experimentally, including anthracene, [8][9][10][11] phenanthrene, 12, 13 pyrene, 4, 5, 14-20 tetracene, 13 pentacene, 13 and diazapentacene. 21 Recent ab initio calculations 22,23 have focussed on the adsorption of planar unsaturated aromatic molecules onto a range of small-diameter CNTs.…”

Section: Introductionmentioning

confidence: 99%

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A study of planar anchor groups for graphene-based single-molecule electronics

Bailey¹,

Visontai²,

Lambert³

et al. 2014

The Journal of Chemical Physics

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Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details. To identify families of stable planar anchor groups for use in single molecule electronics, we report detailed results for the binding energies of two families of anthracene and pyrene derivatives adsorbed onto graphene. We find that all the selected derivatives functionalized with either electron donating or electron accepting substituents bind more strongly to graphene than the parent non-functionalized anthracene or pyrene. The binding energy is sensitive to the detailed atomic alignment of substituent groups over the graphene substrate leading to larger than expected binding energies for -OH and -CN derivatives. Furthermore, the ordering of the binding energies within the anthracene and pyrene series does not simply follow the electron affinities of the substituents. Energy barriers to rotation or displacement on the graphene surface are much lower than binding energies for adsorption and therefore at room temperature, although the molecules are bound to the graphene, they are almost free to move along the graphene surface. Binding energies can be increased by incorporating electrically inert side chains and are sensitive to the conformation of such chains. © 2014 AIP Publishing LLC.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A study of planar anchor groups for graphene-based single-molecule electronics

Bailey¹,

Visontai²,

Lambert³

et al. 2014

The Journal of Chemical Physics

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“…In particular, aromatic molecules, such as pyrene, porphyrin, and their derivatives, can interact with the sidewalls of CNTs by means of π-π stacking interactions [139,140]. Among the main reasons to prepare dendronized CNTs, it is worth mentioning the enhancement of their dispersibility in all type of solvents, especially in water, for biological applications [92,[141][142][143][144][145][146].…”

Section: Dendronized Cntsmentioning

confidence: 99%

Dendronization: A Useful Synthetic Strategy to Prepare Multifunctional Materials

et al. 2012

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Dendronization is a synthetic methodology that offers important advantages.The resulting products, which are called dendronized materials, present new and specific properties. This review shows numerous examples in which individual dendrons are used as building blocks to prepare more complex arrays via covalent or non-covalent interactions. In particular, it points out how the structural information programmed into the dendritic architecture can be used in the dendronization process to generate nanostructures with specific tailored properties. We emphasize the use of different dendrons, with diverse chemical structure and size, to functionalize diverse substrates like linear polymers, and plane and curved inorganic surfaces. Apart from this, the review also demonstrates that self-assembly represents an ideal approach to create well-defined hyperbranched surfaces and it includes some discussion about the ability of both organic and inorganic building blocks to direct this process.

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“…Effective anchoring groups include polycyclic aromatic species such as anthracene, 22 pyrene, 7,23 perylene, 10,21,24,25 porphyrin derivatives 26 and more complex "nanotweezer" systems. 27,28 Suitable hydrophilic moieties include carboxylate, ammonium and sulfonate salts, 9 polyethylene glycol (PEG) derivatives 23 and Newkome 7,21,24,27 and glycerol 25 dendrons.…”

Section: Introductionmentioning

confidence: 99%

Key role of the linker in pyrene-linker-carboxylate surfactants for the efficient aqueous dispersion of multiwalled carbon nanotubes

et al. 2015

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. (2015) 'Key role of the linker in pyrene-linker-carboxylate surfactants for the ecient aqueous dispersion of multiwalled carbon nanotubes.', RSC advances., 5 (115). pp. 95360-95368.Further information on publisher's website:http://dx.doi.org/10.1039/C5RA20250GPublisher's copyright statement:Additional information: Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details. This study establishes that the structure of the linker group between the hydrophobic and hydrophilic units in the new surfactants 1-13 plays an important role in the dispersibility of multiwalled carbon nanotubes (MWNTs) in water. Systematic variation of the linker group in amphiphilic surfactants for carbon nanotubes has not been previously investigated. In the present series, the hydrophobic unit is derived from pyrene, the hydrophilic unit comprises 1-9 carboxylate groups and the linker is based on amide or ether moieties. The resulting MWNTsurfactant dispersions, up to concentrations and efficiencies of ca. 160 mg L -1 and almost 50%, respectively, have been characterised by UV-Vis absorption spectroscopy studies which provide detailed structure-property relationships, while transmission electron microscopy (TEM) was used to confirm that the MWNTs were well dispersed. For many of the new surfactants enhanced dispersion efficiency is observed compared to commercial surfactants. The efficiency of dispersion is affected by the presence, functionality and particularly the length of the linker, and also the number of terminal carboxylate units. The marked effect of sodium, potassium and calcium cations on the dispersion behaviour is explained by interactions between the metal ions and the surfactant and an ionic screening mechanism. We also demonstrate that the dispersibility of the MWNT-surfactant dispersions can be reversibly switched "off" and "on" by addition of acid and base, respectively. The experimental results are supported by theoretical calculations of solvation energy ΔE S . This study represents a significant advance in the design of multi-functional surfactants for efficient aqueous dispersion of carbon-based materials.

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Light-induced Electron Transfer on the Single Wall Carbon Nanotube Surrounded in Anthracene Dendron in Aqueous Solution

Cited by 35 publications

References 7 publications

A study of planar anchor groups for graphene-based single-molecule electronics

A study of planar anchor groups for graphene-based single-molecule electronics

Dendronization: A Useful Synthetic Strategy to Prepare Multifunctional Materials

Key role of the linker in pyrene-linker-carboxylate surfactants for the efficient aqueous dispersion of multiwalled carbon nanotubes

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