Adsorption of phenolic compounds by carbon nanotubes: role of aromaticity and substitution of hydroxyl groups.

With increasing production and application of carbon nanotubes (CNTs), it becomes necessary to understand the interaction between CNTs and aromatic compounds, an important group of organic contaminants and structural components of large organic molecules in biological systems. However, so far few experimental studies have been conducted to systematically investigate the sorption mechanism of polar aromatics to CNTs. Therefore, cyclohexanol, phenol, catechol, pyrogallol, 2-phenylphenol, 1-naphthol, and naphthalene were selected to investigate the role of aromatic structure and -OH substitution in the polar aromatics-CNTs system. Sorption affinity of these compounds by CNTs increased with increasing number of aromatic rings, with an order of cyclohexanol < phenol < 2-phenylphenol < 1-naphthol, and was greatly enhanced by -OH substitution, with an order of phenol (1 -OH) < catechol (2 -OH) < pyrogallol(3-OH). Four possible solute-sorbent interactions, i.e., hydrophobic effect, electrostatic interaction, hydrogen bonding, and pi-pi bonds, were discussed to addressthe underlying mechanism of the enhanced sorption affinity by -OH substitution. It was evident that electron-donating substitution on the aromatic rings strengthened the pi-pi interaction between the aromatics and CNTs and thus the adsorption affinity. These results will advance the understanding of the sorption behavior of CNTs in the environmental systems.