Preparation and evaluation of a perylenediimide bridged bis(β-cyclodextrin) chiral stationary phase for HPLC

A large pi-conjugated perylenediimide bridged bis(beta-cyclodextrin)-bonded stationary phase (PBCDP) was first prepared and characterized. The chiral HPLC performance was systematically evaluated using a series of chiral probes. The results showed that PBCDP could resolve 36 kinds of chiral compounds in reversed-phase and polar organic modes with high resolutions (Rs) 1.48-3.28 for profens, 1.25-2.85 for triazoles, 1.34-5.29 for flavanones, 1.66-4.58 for amino acids and 1.22-1.97 for beta-blockers. Especially, PBCDP could completely resolve acidic non-steroidal chiral drugs (profens) and simultaneously resolve basic five triazole pesticides, which were difficult to separate by ordinary CDCSP. Compared with CDCSP (15 kinds), the new stationary phase has a wider resolution range (36 kinds). Obviously, the synergistic inclusion of the two cavities of bridged cyclodextrin, as well as the large pi-pi stacking, hydrogen bond, dipole-dipole and basic primary amine site (-NH-) provided by the perylenediimide bridging group contributed together to the improvement of the above chiral separations. PBCDP was a new type of versatile chiral separation material without port derivatization.

Automated summary

A new type of perylenediimide bridged bis(beta-cyclodextrin)-bonded stationary phase was successfully prepared and characterized. The chiral HPLC performance of this stationary phase was systematically evaluated, and it showed high resolutions for a wide range of chiral compounds. The excellent chiral separation capability of this material can be attributed to the synergistic effects of the bridged cyclodextrin cavities and the large pi-pi stacking, hydrogen bond, dipole-dipole, and basic primary amine site (-NH-) provided by the perylenediimide bridging group.