基于螺烯的新型手性有机分子笼.

朱新远

Organic cages are a type of three-dimensional organic molecules with unique hollow structures, and show a wide range of potential applications in molecular recognition and separation, catalysis, gas adsorption and storage, etc. The function of these organic cages highly depends on the chemical structure and linkage of the molecular building blocks. However, it remains a challenge to expand the category of suitable molecular precursors, especially for chiral organic cages. Recently, Prof. Qiu Huibin and co-workers at Shanghai Jiao Tong University developed a new series of chiral organic cages using helicenes as building blocks. Chiral organic cages was synthesized via a process involving formation of reversible dynamic covalent bonds, and their chiral recognition and resolution, circularly polarized luminescence and molecular switching properties were investigated. In their current studies, a [3 2]-type cage was constructed adopting [6]helicene as the building blocks. Three helicene units were arranged in a propeller-like fashion, giving rise to an integrally triple-stranded helical structure for the cage skeleton. This structural chirality presented high stability in organic solvents as well, showing strong diastereotopy effect as observed from NMR spectra and unique structured circular dichroism signals. Besides, these chiral organic cages showed outstanding enantioselectivity against a series of small chiral molecules. The innovative strategy to construct organic cages using nonplanar, helical molecules as building blocks provided a new access to advanced functional organic porous materials

MOLECULAR structure; RESOLUTION (Chemistry); CHEMICAL structure; POROUS materials; CHIRAL recognition; KINETIC resolution; HELICAL structure; MOLECULAR recognition

Journal of Functional Polymers, 2019, Vol 32, Issue 4, p408

1008-9357

Academic Journal

10.14133/j.cnki.1008-9357.20190509001