Multi-Level Chirality Transferring from Amino Acid Derivatives to CPL-Active Nanoparticles in Aqueous Medium.

Chirality at different levels is widely observed in nature, but the clue to connect them together, and the way how the chirality transfers among different levels are still obscure. Herein, we constructed a L-/D-lysine-based self-assembly system, in which two-step chirality transferring among three different levels was observed in aqueous solution. The chirality was originated from the point chirality of amino acid derivatives L-/D-PyLys hydrochlorides, and transferred to the planar conformational chirality of water-soluble pillar[5]arene pR-/pS-WP5. Then, with the aid of pR-/pS-WP5, nanoparticles were formed that exhibited L-/R-handed circularly polarized luminescence with a dissymmetry factor up to ±0.001, arising from pyrene excimers arranged in the chiral manner. This multi-level chirality transferring not only provides a perspective to trace potential clue, and to pursue certain way by which the chirality transfers, but also offers a strategy to arise the controllable CPL emission in aqueous medium.