High Population of Individualized SWCNTs through the Adsorption of Water-Soluble Perylenes

Abstract

The aqueous dispersion of SWCNTs in the presence of the water-soluble perylene derivatives 1-3 is reported. Significantly, even very low concentrations of the perylenes such as 0.01 wt% of the amphiphilic derivative 3, cause an efficient dissolution of the SWCNTs in water accompanied by a very pronounced individualization. The individualization of SWCNTs in water after ultrasonication in the presence of water-soluble aromatic perylenes was investigated in detail by absorption, emission, and Raman spectroscopy as well as by AFM and cryo-TEM. These studies also revealed that the individualization of the SWCNTs caused by the adsorption of 3 is much more effective than that induced by SDBS, which is the most frequently used surfactant for SWCNT dispersion in water. The pi-pi-stacking interaction and the electronic interaction between the perylene unit and the nanotube surface is reflected, for example, by the distinct absorption and emission features in the UV/vis/nIR, which differ significantly from those observed for SWNTs dispersed in the presence of SDBS and by the quenching of the perylene fluorescence of 3 when being in contact with the tubes.

Interactions Between Amino Acid‐Tagged Naphthalenediimide and Single Walled Carbon Nanotubes for the Design and Construction of New Bioimaging Probes

“…The S 22 and S 11 band are sharp compared similar to those observed in perylene-SWNTs composites. [12,13] Since these transition energies are related to the size of the SWNT bundles and the presence of isolated tubes in solution have been reported to give rise to sharp, well-resolved peaks, [29] UV-vis-nIR spectroscopy of the NDI@SWNT composite suggests that NDI is capable of efficient de-bundling of the SWNT strands in these common solvents.…”

“…tailor-made porphyrin hosts [11] or strong electron acceptors such as water solubile perylenes [12][13][14] ) has been a lively area of exploration in the quest for new nanohybrids with potential applications ranging from new luminescent materials for solar cells [12,13] to molecular imaging tools. [5,6,8,9,13, Naphthalenediimides (NDI) are emerging both as a building block for organic nanotube creation [37] and as a promising class of chromophores because of their strong absorption and fluorescence emission at visible and near IR wavelengths. [38] NDI fluorescence emissions show maxima between 300-800 nm, including in the spectral region where the interference from the autofluorescence of living cells may be bypassed; this makes them attractive candidates as building blocks for optical imaging probes.…”

“…A new hybrid material, NDI@SWNT, was prepared and characterized as dispersed in organic solvents and aqueous media and in the solid state by HR TEM, tapping mode atomic force microscopy (TM AFM), scanning electron microscopy (SEM), circular dichroism, Raman and fluorescence spectroscopies (steady-state single and two-photon techniques). We have been interested in the design and spectroscopic investigation of new nanomaterials with light emitting properties.[67] The NDI nanotubular receptor recently developed [55] should have the ability to bind via donor-acceptor interactions to carbon nanomaterials, in an analogous manner to that found in the exciting new hybrids containing perylenes in SWNTselectron acceptor composites for photovoltaic applications, reported by the groups of Hirsch [12][13][14] and Guldi.[14]We report our investigations at the formation of a new nanohybrid, denoted NDI@SWNT, in solution and on a preparative scale. We report here for the first time, the recognition and coating of the aromatic surface of ultra-purified SWNTs (provided by Thomas Swan Ltd, Elicarb SWNTs, and further steampuriffied to ensure they are free of catalytic impurities or carbonaceous materials from the nanotube synthesis, Supplementary Information) by a new iodine-and amino acid-derivatized NDI.…”

Soluble Graphene: Generation of Aqueous Graphene Solutions Aided by a Perylenebisimide‐Based Bolaamphiphile

“…These rely either on organic solvents [15] or on the use of graphene oxide (GO) [16][17][18][19][20] containing a large number of defects, which leads to considerable disruption of the favorable electronic properties found in parent graphene. [15,19,[21][22][23][24] Inspired by our recent success in exfoliating and doping of single-walled carbon nanotubes (SWNTs), [25,26] which opens up the possibility of modifying charge carrier concentration of the produced graphene in solution, and the work conducted on solubilization of graphene with sodium dodecylbenzene sulfonate (SDBS) starting from graphite by Coleman and coworkers, [27] we report here a very simple and efficient procedure to disperse graphene by means of ultrasonic treatment of graphite in water aided by the highly water soluble perylene-based bolaamphiphile detergent 1. [28] While ultrasonication serves to overcome the strong van der Waals interactions between the graphene planes in the graphite mother crystals, the detergent guarantees stabilization of the exfoliated sheets of few-layer (FLG) and single-layer graphene (SLG) in water driven by p-p-stacking interactions and the hydrophobic effect, comparable to other aromatic systems.…”

Hybrid materials of 1D and 2D carbon allotropes and synthetic π-systems

“…12) was also used to disperse SWNTs in water 73,74 . The polar carboxyl groups led to enhanced water solubility, and the nonpolar perylene moiety facilitated the dispersion of SWNTs.…”