Unique Separation Behavior of a C60 Fullerene-Bonded Silica Monolith Prepared by an Effective Thermal Coupling Agent

• Published in: Chemistry : a European journal 2015-12, Vol.21 (50), p.18095-18098
• Main Authors: Kubo, Takuya, Murakami, Yoshiki, Tsuzuki, Madoka, Kobayashi, Hiroshi, Naito, Toyohiro, Sano, Tomoharu, Yan, Mingdi, Otsuka, Koji
• Format: Article
• Language: English
• Subjects: Chemistry; Chromatography; corannulene; Fullerenes; pi interactions; silica monolith; spherical recognition
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201503898

Herein, we report a newly developed C60 fullerene‐bonded silica monolith in a capillary with unique retention behavior due to the structure of C60 fullerene. N‐Hydroxysuccinimide (NHS)‐conjugated C60 fullerene was successfully synthesized by a thermal coupling agent, perfluorophenyl azide (PFPA), and assigned by spectroscopic analyses. Then, NHS‐PFPA‐C60 fullerene was attached onto the surface of a silica monolith in a capillary. The capillary provided specific separation ability for polycyclic aromatic hydrocarbons in liquid chromatography by an effective π–π interaction. Furthermore, corannulene, which has a hemispherical structure, was selectively retained in the capillary based on the specific structural recognition due to the spherical C60 fullerene. This is the first report revealing the spherical recognition ability by C60 fullerene in liquid chromatographic separation. Spherical recognition: A C60 fullerene‐bonded silica monolithic medium was prepared by using a thermal coupling agent conjugated with C60 fullerene. The C60 fullerene‐bonded monolith prepared in a capillary showed a very strong π–π interaction in liquid chromatography. Also, the hemispherical molecule corannulene was dramatically retained in the C60 fullerene‐bonded monolith by the unique molecular recognition based on a buckyball (see figure).