College of Chemistry, Nanchang University, Nanchang, 330031, China.
Anal Sci. 2022 Jul;38(7):989-1002. doi: 10.1007/s44211-022-00130-6. Epub 2022 May 31.
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 (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 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.
首次制备并表征了一种大π共轭苝二酰亚胺桥联双（β-环糊精）键合固定相（PBCDP）。使用一系列手性探针系统地评估了手性 HPLC 性能。结果表明，PBCDP 可以在反相和极性有机模式下拆分 36 种手性化合物，对普罗芬的分辨率（Rs）为 1.48-3.28，三唑的分辨率为 1.25-2.85，黄烷酮的分辨率为 1.34-5.29，氨基酸的分辨率为 1.66-4.58，β-阻滞剂的分辨率为 1.22-1.97。特别是，PBCDP 可以完全拆分酸性非甾体手性药物（普罗芬），同时拆分普通 CDCSP 难以分离的碱性五种三唑类农药。与 CDCSP（15 种）相比，新固定相的分辨率范围更广（36 种）。显然，桥联环糊精的两个空腔的协同包合作用，以及苝二酰亚胺桥联基团提供的大π-π堆积、氢键、偶极-偶极和碱性伯胺（-NH-）一起有助于改善上述手性分离。PBCDP 是一种新型通用手性分离材料，无需端口衍生化。
