Supramolecular Chemistry-Based One-Pot High-Efficiency Separation of Solubilizer-Free Pure Semiconducting Single-Walled Carbon Nanotubes: Molecular Strategy and Mechanism

Nakashima, Naotoshi; Fukuzawa, Masashi; Nishimura, Kanako; Fujigaya, Tsuyohiko; Kato, Yuichi; Staykov, Aleksandar

doi:10.1021/jacs.0c03994

Cited by 19 publications

(44 citation statements)

References 43 publications

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“…However, in most of the reports, only s-SWCNTs with diameters below 1 nm were sorted . Selective extracting with polymers − and supramolecules − has been intensively applied for s-SWCNTs both below and beyond 1 nm due to its simplicity and high selectivity. Polyfluorene (PFO) has shown great success in extracting subnanometer s-SWCNTs from commerical CoMoCAT (0.7–0.9 nm) and HiPCO (0.8–1.2 nm) SWCNTs.…”

Section: Introductionmentioning

confidence: 99%

Host–Guest Molecular Interaction Enabled Separation of Large-Diameter Semiconducting Single-Walled Carbon Nanotubes

Yang

Liu

et al. 2021

J. Am. Chem. Soc.

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Semiconducting single-walled carbon nanotubes (s-SWCNTs) with a diameter of around 1.0–1.5 nm, which present bandgaps comparable to silicon, are highly desired for electronic applications. Therefore, the preparation of s-SWCNTs of such diameters has been attracting great attention. The inner surface of SWCNTs has a suitable curvature and large contacting area, which is attractive in host–guest chemistry triggered by electron transfer. Here we reported a strategy of host–guest molecular interaction between SWCNTs and inner clusters with designed size, thus selectively separating s-SWCNTs of expected diameters. When polyoxometalate clusters of ∼1 nm in size were filled in the inner cavities of SWCNTs, s-SWCNTs with diameters concentrated at ∼1.3–1.4 nm were selectively extracted with the purity of ∼98% by a commercially available polyfluorene derivative. The field-effect transistors built from the sorted s-SWCNTs showed a typical behavior of semiconductors. The sorting mechanisms associated with size-dependent electron transfer from nanotubes to inner polyoxometalate were revealed by the spectroscopic and in situ electron microscopic evidence as well as the theoretical calculation. The polyoxometalates with designable size and redox property enable the flexible regulation of interaction between the nanotubes and the clusters, thus tuning the diameter of sorted s-SWCNTs. The present sorting strategy is simple and should be generally feasible in other SWCNT sorting techniques, bringing both great easiness in dispersant design and improved selectivity.

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Section: Introductionmentioning

confidence: 99%

Host–Guest Molecular Interaction Enabled Separation of Large-Diameter Semiconducting Single-Walled Carbon Nanotubes

Yang

Liu

et al. 2021

J. Am. Chem. Soc.

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“…[128] The formation of a helical ribbon of flavin mononucleotide (FMN) around nanotubes was attributed to the cooperative hydrogen bonding between adjacent flavin moieties under concentric 𝜋-𝜋 interactions with nanotube surfaces. [128] Although the nucleotides have demonstrated certain ability for the structure recognition of SWCNTs in subsequent studies, [129,[158][159][160][161] their efficiencies for dispersion and separation are still limited, compared with the widely used ssDNA and conjugated polymers mentioned above.…”

Section: Biomoleculesmentioning

confidence: 99%

Recent Advances in Structure Separation of Single‐Wall Carbon Nanotubes and Their Application in Optics, Electronics, and Optoelectronics

Wei

Wang

et al. 2022

Advanced Science

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Structural control of single-wall carbon nanotubes (SWCNTs) with uniform properties is critical not only for their property modulation and functional design but also for applications in electronics, optics, and optoelectronics. To achieve this goal, various separation techniques have been developed in the past 20 years through which separation of high-purity semiconducting/metallic SWCNTs, single-chirality species, and even their enantiomers have been achieved. This progress has promoted the property modulation of SWCNTs and the development of SWCNT-based optoelectronic devices. Here, the recent advances in the structure separation of SWCNTs are reviewed, from metallic/semiconducting SWCNTs, to single-chirality species, and to enantiomers by several typical separation techniques and the application of the corresponding sorted SWCNTs. Based on the separation procedure, efficiency, and scalability, as well as, the separable SWCNT species, purity, and quantity, the advantages and disadvantages of various separation techniques are compared. Combined with the requirements of SWCNT application, the challenges, prospects, and development direction of structure separation are further discussed.

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“…Thus, the separation/purification of the s-SWCNTs on the basis of their chiralities is still one of the most important issues in the science and applications of carbon nanotubes. Many approaches have already been reported regarding s-SWCNT sorting − from as-synthesized SWCNTs, which are a mixture of s-SWCNTs and met-SWCNTs, while many of them are complex in the separation. For one-pot easy separation, we need to design a suitable solubilizer by an organic/polymer synthesis method.…”

Section: Introductionmentioning

confidence: 99%

One-Pot Separation of Semiconducting Single-Walled Carbon Nanotubes and Their Enantiomer Recognition Based on Self-Organized Supramolecular Riboflavin (Vitamin B2) Motifs

et al. 2022

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The development of a facile method to sort semiconducting single-walled carbon nanotubes (s-SWCNTs) and their enantiomer recognition are still great challenges. We here describe a finding that a commercially available, safe, and cost-effective hydrophobic riboflavin analogue (riboflavin tetrabutyrate; RTB) efficiently sorts only s-SWCNTs by a one-pot method (bath-type sonication for 30 min followed by ultracentrifugation) and recognizes their enantiomers (left- and right-handed s-SWCNTs). The solubilization behavior of the SWCNTs strongly depends on the concentration of RTB; namely, with the decrease in the concentration of RTB, the s-SWCNT (n,m)-chiral selective sorting efficiency is enhanced. When using RTB = ∼0.4 mM (SWCNTs = 1 mg/3 mL toluene), two (n,m) chiralities of the s-SWCNTs with (n,m) = (8,6) and (8,7) were efficiently sorted. Furthermore, when using RTB = 0.5–1 mM, the SWCNT enantiomer recognition was observed. In addition, the X-ray photoelectron spectroscopic study revealed that the adsorbed RTB molecules on the s-SWCNTs were readily removed by simple rinsing with acetone to provide adsorbent-free pure s-SWCNTs. On the basis of the experimentally obtained data using Raman, photoluminescence, and visible–near-IR absorption spectroscopy techniques and computational density functional theory (DFT) approaches, we have revealed a possible mechanism for this unique s-SWCNT selective sorting and their enantiomer recognition. The supramolecular orientation of RTB into the helical superlattice with its own chirality provides a mechanism for chirality recognition. The study demonstrates one-pot sorting of s-SWCNTs and their enantiomer recognition using a cost-effective, safe molecule. Such a study is important for s-SWCNT separation science and its application in nanoscience and engineering areas.

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Supramolecular Chemistry-Based One-Pot High-Efficiency Separation of Solubilizer-Free Pure Semiconducting Single-Walled Carbon Nanotubes: Molecular Strategy and Mechanism

Cited by 19 publications

References 43 publications

Host–Guest Molecular Interaction Enabled Separation of Large-Diameter Semiconducting Single-Walled Carbon Nanotubes

Host–Guest Molecular Interaction Enabled Separation of Large-Diameter Semiconducting Single-Walled Carbon Nanotubes

Recent Advances in Structure Separation of Single‐Wall Carbon Nanotubes and Their Application in Optics, Electronics, and Optoelectronics

One-Pot Separation of Semiconducting Single-Walled Carbon Nanotubes and Their Enantiomer Recognition Based on Self-Organized Supramolecular Riboflavin (Vitamin B2) Motifs

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