Bimodal supramolecular functionalization of carbon nanotubes triggered by covalent bond formation

Leret, Sofía; Pouillon, Yann; Casado, Santos; Navío, Cristina; Rubio, Ángel; Pérez, Emilio M.

doi:10.1039/c6sc03894h

Cited by 31 publications

(34 citation statements)

References 53 publications

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“…We were initially surprised that the Supra‐MINT samples at the plateau level still contain a non‐negligible portion of strongly bound macrocycles. This result is, however, consistent with a structural proposal by Pérez, namely that the macrocycles in MINTs are not prevented from dethreading by terminal stoppers on the nanotubes, but instead by crossing points between several nanotubes, which can be observed by HR‐TEM (Figure S42) and also seem to exist in suspension . In the Supra‐MINT samples, some macrocycles could therefore behave like Ohe's nanohoops and thread onto the non‐stoppered tips of SWCNTs.…”

Section: Resultssupporting

confidence: 89%

Dynamic Covalent Formation of Concave Disulfide Macrocycles Mechanically Interlocked with Single‐Walled Carbon Nanotubes

et al. 2020

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The formation of discrete macrocycles wrapped around single-walled carbon nanotubes (SWCNTs) has recently emerged as an appealing strategy to functionalize these carbon nanomaterials and modify their properties.H ere,w e demonstrate that the reversible disulfide exchange reaction, which proceeds under mild conditions,c an install relatively large amounts of mechanically interlocked disulfide macrocycles on the one-dimensional nanotubes.S ize-selective functionalization of am ixture of SWCNTs of different diameters were observed, presumably arising from error correction and the presence of relatively rigid, curved p-systems in the key building blocks.Acombination of UV/Vis/NIR, Raman, photoluminescence excitation, and transient absorption spectroscopyindicated that the small (6,4)-SWCNTs were predominantly functionalizedbythe small macrocycles 1 2 ,whereas the larger (6,5)-SWCNTs were an ideal matchf or the larger macrocycles 2 2 .T his sizes electivity,w hich was rationalized computationally,c ould prove useful for the purification of nanotube mixtures,s ince the disulfide macrocycles can be removed quantitatively under mild reductive conditions.

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Section: Resultssupporting

confidence: 89%

Dynamic Covalent Formation of Concave Disulfide Macrocycles Mechanically Interlocked with Single‐Walled Carbon Nanotubes

et al. 2020

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“…Clipping strategy for the synthesis of MINTs: U-shaped molecules featuring two units of ar ecognition motif for SWNTsa re allowed to interact with them via a supramolecular equilibrium, governed by its association constant (K a ), the associates are thens titcheda round the SWNTsvia ring-closing metathesis (RCM),ap rocess that showsp seudo-first order kinetics( k RCM ). c) Schematic structureo fthe U-shaped molecules and some of the recognition motifs that we have used so far to synthesize MINTs, including electrondonor exTTF, [23] electron acceptor NDI, [51] and electronicallyn eutral pyr. [52] The Characterization Challenge:Comparing Cartoons to Reality Experimentally,n ano-horseshoet hrowing is rather simple.…”

Section: Introductionmentioning

confidence: 99%

Putting Rings around Carbon Nanotubes

Pérez

2017

Chemistry A European J

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In the last five years, we have developed synthetic methods towards encapsulation of single-walled carbon nanotubes (SWNTs) into organic macrocycles, to form rotaxane-type molecules. These are the first examples of mechanically interlocked SWNT derivatives (MINTs). In this article, the motivation to continue developing the chemistry of SWNTs at a time well past their hype is discussed and our synthetic strategy and characterization methodology is explained in detail, stressing the general aspects. In particular, special emphasis is placed on the importance of adequate control experiments and bulk spectroscopic and analytical data to determine the structure of SWNT derivatives, as opposed to relying only (or mostly) on microscopy. Also our experimental results are used as pretext to reflect on more general/conceptual issues pertaining to the chemistry of SWNTs and mechanically interlocked molecules.

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“…The formation of an initial NDI-Bola layer via NDI-SWNT stacking, rather than cation-p interactions could potentially bridge the gap, thereby alleviating the discrepancy. This well-known NDI-SWNT assembly mode [70][71][72] would also create a hydrophilic SWNT surface that would be more compatible with the polar NDI-Bola nanotube interior. However, inspection of the TEM images of the composite revealed SWNT diameters of 2.1-2.3 nm, similar to the starting dimensions of the debundled SWNTs (Fig.…”

Section: Resultsmentioning

confidence: 99%

Threading carbon nanotubes through a self-assembled nanotube

Mason

Modarelli

et al. 2019

Chem. Sci.

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Bimodal supramolecular functionalization of carbon nanotubes triggered by covalent bond formation

Abstract: We describe naphthalene diimide–SWNT supramolecular hybrids in which the topology, the degree of functionalization, and the electronic interaction can be controlled.

Cited by 31 publications

References 53 publications

Dynamic Covalent Formation of Concave Disulfide Macrocycles Mechanically Interlocked with Single‐Walled Carbon Nanotubes

Dynamic Covalent Formation of Concave Disulfide Macrocycles Mechanically Interlocked with Single‐Walled Carbon Nanotubes

Putting Rings around Carbon Nanotubes

Threading carbon nanotubes through a self-assembled nanotube

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