Peng Haiqing, Alemany Lawrence B, Margrave John L, Khabashesku Valery N
Department of Chemistry and the Center for Nanoscale Science and Technology, Rice University, 6100 Main Street, Houston, Texas 77005-1892, USA.
J Am Chem Soc. 2003 Dec 10;125(49):15174-82. doi: 10.1021/ja037746s.
The reactions of single-walled carbon nanotubes (SWNTs) with succinic or glutaric acid acyl peroxides in o-dichlorobenzene at 80-90 degrees C resulted in the addition of 2-carboxyethyl or 3-carboxypropyl groups, respectively, to the sidewalls of the SWNT. These acid-functionalized SWNTs were converted to acid chlorides by derivatization with SOCl(2) and then to amides with terminal diamines such as ethylenediamine, 4,4'-methylenebis(cyclohexylamine), and diethyltoluenediamine. The acid-functionalized SWNTs and the amide derivatives were characterized by a set of materials characterization methods including attenuated total reflectance (ATR) FTIR, Raman and solid state (13)C NMR spectroscopy, transmission electron microscopy (TEM), and thermal gravimetry-mass spectrometry (TG-MS). The degree of SWNT sidewall functionalization with the acid-terminated groups was estimated as 1 in 24 carbons on the basis of TG-MS data. In comparison with the pristine SWNTs, the acid-functionalized SWNTs show an improved solubility in polar solvents, for example, alcohols and water, which enables their processing for incorporation into polymer composite structures as well as for a variety of biomedical applications.
单壁碳纳米管（SWNTs）与琥珀酸或戊二酸酰基过氧化物在邻二氯苯中于80 - 90℃反应，分别导致SWNT侧壁上添加了2 - 羧乙基或3 - 羧丙基。这些酸官能化的SWNTs通过用SOCl₂衍生化转化为酰氯，然后与乙二胺、4,4'-亚甲基双（环己胺）和二乙基甲苯二胺等末端二胺反应转化为酰胺。酸官能化的SWNTs和酰胺衍生物通过一系列材料表征方法进行表征，包括衰减全反射（ATR）傅里叶变换红外光谱、拉曼光谱和固态¹³C核磁共振光谱、透射电子显微镜（TEM）以及热重 - 质谱联用（TG - MS）。根据TG - MS数据，酸封端基团对SWNT侧壁的官能化程度估计为每24个碳原子中有1个。与原始SWNTs相比，酸官能化的SWNTs在极性溶剂（如醇类和水）中的溶解度有所提高，这使得它们能够被加工用于掺入聚合物复合结构以及用于各种生物医学应用。
