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

A large π-conjugated perylenediimide bridged bis (β-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 ( R s) 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 β-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 π–π 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. Graphical abstract