Functionalization of Carbon Nanohorns with Azomethine Ylides: Towards Solubility Enhancement and Electron‐Transfer Processes

Abstract

Water‐soluble carbon nanohorns have been synthesized via the 1,3‐dipolar cycloaddition reaction of azomethine ylides (see figure). The introduction of fused substituted pyrrolidine rings onto the π‐skeleton of the nanohorns enhances solubility and generates materials potentially suitable for managing electron‐transfer processes.

Nanocomposite Made of an Oligo(p‐phenylenevinylene)‐Based Trihybrid Thixotropic Metallo(organo)gel Comprising Nanoscale Metal–Organic Particles, Carbon Nanohorns, and Silver Nanoparticles

“…On the other hand, the use of CNHs, a recently discovered carbon allotrope,19a is advantageous because of their outstanding ability to disperse smoothly when integrated with other materials 19a. Dispersion of SWCNHs could be achieved evenly through π–π interactions with π‐aromatic molecules 19a. Therefore, we attempted solubilization of SWCNHs in the metallogel matrix.…”

“…Individual SWCNHs with conical tips self‐aggregate into dahlia flowerlike superstructures in the nanoscale dimension due to strong intermolecular π‐stacking interactions (Figure S7 in the Supporting Information). Easier dispersibility of SWCNHs compared with the tightly bundled SWCNTs may be attributed to the weak van der Waals interactions among the superstructures of SWCNHs due to the rough surface structure of the latter 19a. Recently, SWCNH‐based nanostructured materials have been utilized in various applications that range from materials science to biomedicine 19a…”

Cycloaddition Reactions of Butadiene and 1,3‐Dipoles to Curved Arenes, Fullerenes, and Nanotubes: Theoretical Evaluation of the Role of Distortion Energies on Activation Barriers

“…at the B3LYP/6-31G(d)//AM1 level, where the closed [6,6] adducts were predicted as the most stable ones and a concerted mechanism was followed. [20] The 1,3-dipolar cycloadditions of azomethine ylides to other carbon nanostructures, such as carbon nanotubes (CNTs), [21][22][23][24][25] nanofibers, [26] nanohorns, [27] nanoonions, [28,29] and nanorods, [30] have been reported. Although most studies of the functionalization of carbon nanotubes through 1,3-dipolar cycloaddition reactions involve the addition of azomethine ylides, the reactions with other 1,3-dipoles such as nitrile imines and ozone have also been achieved.…”

Interfacing Functionalized Carbon Nanohorns with Primary Phagocytic Cells

“…The problem of CNH solubility has been partially solved as a certain number of organic reactions can be applied to functionalize them, which makes their manipulation easier and improves their biocompatibility. [10][11][12][13] f-CNHs have been proposed for controlled drug release of anti-inflammatory and anticancer agents including dexamethasone, cis-platin, and doxorubicin. [3][4][5][6][7][8] Alternatively, CNHs have been modified with magnetite and administered in vivo for magnetic resonance imaging (MRI) applications.…”