Enhancement of Water Solubility of Single-Walled Carbon Nanotubes by Formation of Host−Guest Complexes of Cyclodextrins with Various Guest Molecules

Abstract

Solubilization of single-walled carbon nanotubes (SWNTs) by physical adsorption of cyclodextrins (CDs), guest molecules, and host-guest complexes was investigated. As guest compounds, sodium adamantanecarboxylate (AdCNa), sodium dodecylbenzenesulfonate (SDBS), sodium ursodeoxycholate (UdCNa), sodium ferrocenecarboxylate (FeCNa), and TritonX-405 were employed. As host compounds, R-, β-, and γ-cyclodextrins (R-, β-, and γ-CDs) were used. By using CDs as a solubilizing agent, SWNTs were insoluble in aqueous media. In the presence of AdCNa and FeCNa, solubility of SWNTs was dramatically increased by formation of host-guest complex with βor γ-CDs. By using SDBS-CD complexes, solubility of SWNTs was also enhanced compared to only guest molecules. On the other hand, solubility of SWNTs was decreased by formation of host-guest complexes of UdCNa and TritonX-405 with CDs. Formation of host-guest complex mostly resulted in enhancement of water solubility of SWNTs.

Theoretical insights into the host-guest interactions between [6]cycloparaphenyleneacetylene and its anthracene-containing derivative and fullerene C70

“…Because of their unique structures and superior properties for molecular devices, host-guest complexes based on various noncovalent interactions are one of the most popular supramolecular systems in recent years. [1][2][3][4][5][6][7][8][9] Fullerenes, as π-conjugated spherical guest molecules, are attractive nanosized molecules (∼1 nm in diameter) with applications in a wide range of fields from material science to pharmacy. [10] Consequently, numerous well-ordered fullerene-based nanostructures have been designed.…”

Supramolecular Surface Modification and Solubilization of Single‐Walled Carbon Nanotubes with Cyclodextrin Complexation

“…We noticed that Ogoshi et al recently reported the enhancement of water solubility of SWCNTs by cyclodextrin host-guest complexes with several anionic guest molecules through physical adsorption. [24] Cyclodextrins are a type of cyclic oligosaccharide comprising several glucopyranose units. [25] The sub-nanometer hydrophobic cavity can include a wide variety of organic molecules that are water insoluble, thus, making them "dissolve" in water through the help of the hydrophilic exterior surface of cyclodextrins.…”

Emergence in the functionalized carbon nanotubes as smart nanocarriers for drug delivery applications

“…The f-CNTs also have beneficial aspects of delivering several hydrophobic biomolecules (e.g., proteins, peptides, nucleic acids, enzymes) to enhance their bioavailability. SWCNTs have the advantage of formation of hostÀguest complexes with cyclodextrins for improving the solubility and deliverability of various guest drug molecules (Ogoshi et al, 2008).…”