Hashimoto Yoshihisa, Tanaka Yuya, Suzuki Daiya, Imai Yoshitane, Yoshizawa Michito
Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama 226-8503, Japan.
Graduate School of Science and Engineering, Kindai University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan.
J Am Chem Soc. 2024 Aug 28;146(34):23669-23673. doi: 10.1021/jacs.4c07193. Epub 2024 Aug 19.
For the design of a new chiroptically active host-guest system, a bent amphiphilic compound was synthesized using cyclic monoterpenes as key biorelated chiral frameworks. In water, the bent amphiphiles form a terpene-based micellar capsule with a core diameter of ∼2 nm in a spontaneous and quantitative fashion. The resultant chiral capsule shows wide-ranging uptake abilities toward achiral fluorescent dyes in water. Notably, relatively strong CD bands are generated from the resultant host-guest composites, e.g., possessing AIE-active tetraphenylethene and sterically demanding BODIPY dyes, through efficient host-to-guest chirality transfer. The composites also display CPL, with moderate to high emission asymmetry factors (|| = up to 3.3 × 10).
为了设计一种新的具有手性光活性的主客体体系，使用环状单萜作为关键的生物相关手性骨架合成了一种弯曲的两亲性化合物。在水中，弯曲的两亲性分子以自发且定量的方式形成一种核心直径约为2 nm的基于萜烯的胶束胶囊。所得的手性胶囊对水中的非手性荧光染料具有广泛的摄取能力。值得注意的是，通过有效的主客体手性转移，从所得的主客体复合物中产生了相对较强的圆二色（CD）带，例如含有聚集诱导发光（AIE）活性的四苯乙烯和空间位阻较大的硼二吡咯（BODIPY）染料。这些复合物还表现出圆偏振发光（CPL），具有中等至高的发射不对称因子（||高达3.3×10）。
