Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056, Basel, Switzerland.
Swiss Nanoscience Institute, University of Basel, Klingelbergstrasse 82, 4056, Basel, Switzerland.
Chemistry. 2019 Jan 2;25(1):285-295. doi: 10.1002/chem.201803944. Epub 2018 Nov 8.
The synthesis and characterization of zwitterionic molecular [c2]- and [a2]-daisy chains are described, relying on recognition of a positively charged cyclophane and a negatively charged oligo(phenylene-ethynylene) (OPE) rod in aqueous medium. For this purpose, syntheses of an acetylene-functionalized macrocyclic receptor and a water-soluble OPE-rod as the guest component are presented, from which a heteroditopic daisy chain monomer was prepared. This monomer aggregated strongly in water/methanol 4:1 and formed molecular daisy chains, which were isolated as interlocked species from a stoppering reaction at 1 mm concentration. The cyclic dimer [c2] was the main product with an isolated yield of 30 % and consisted of a mixture of diastereomers, as evidenced by H NMR spectroscopy.
两性离子分子 [c2]-和 [a2]-雏菊花链的合成与表征，依赖于在水介质中识别带正电荷的环芳烷和带负电荷的寡聚（亚苯基乙炔）（OPE）棒。为此，我们合成了一个炔基功能化的大环受体和一个水溶性的 OPE-棒作为客体组分，从这两种物质中制备了一个杂双位雏菊花链单体。该单体在水/甲醇 4:1 中强烈聚集并形成分子雏菊花链，在 1 mm 浓度下通过塞子反应将其作为互锁物种分离。环状二聚体 [c2]是主要产物，其分离产率为 30%，由非对映异构体混合物组成，这一点可通过 H 核磁共振波谱得到证实。
