Self-assembled bamboo-like carbon nanotubes based on chiral H8BINOL sensors to recognize cinchonidine efficiently by diastereoisomer complexes.

Abstract

Fluorescence recognition for the antimalarial cinchonidine could be achieved efficiently and rapidly through bamboo-like carbon nanotubes based on chiral conjugated H8BINOL derivatives. Herein, it was proved that the chiral fluorescence probe H8BINOL exhibited excellent fluorescence identification ability for cinchonidine. The structure and size of the S-1 (S-(3,3'-phenyl)-5,5'6,6',7',8,8'-octahydro-[1,1'-dinaphthalene]-2,2'-diol) and R-1 (R-(3,3'-phenyl)-5,5'6,6',7',8,8'-octahydro-[1,1'-dinaphthalene]-2,2'-diol) were studied by using the DLS, TEM, and SEM spectra, which exhibited a self-assembled bamboo-like carbon nanotube structure. In the CD (circular dichroism) test, cinchonidine was added to a pair of enantiomers of H8BINOL derivatives. The different configurations of H8BINOL derivatives showed significantly different Cotton effects for cinchonidine, indicating that cinchonidine formed diastereoisomer π-π complexes with different configurations of H8BINOL derivatives. From the AFM tests, it was revealed that cinchonidine could effectively quench the fluorescent spot of the probes quickly. The fluorescence titration tests demonstrated that 6.4 × 10-7 mol of cinchonidine could completely quench the fluorescence sensor of S-1 (2 × 10-5 M, 2 mL) through the formation of a 1 : 1 complex. The limit of detection (LOD) of S-1 was calculated to be 6.08 × 10-10, which indicates that S-1 has a high sensitivity and can be applied effectively to the practice of identifying cinchonidine. Meanwhile, the fluorescence sensor R-1 also exhibited the same sensibility with a low limit of detection (7.60 × 10-10).