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Chiroptical Helices of N-terminal Aryl Amino Acids Adaptive to Orthogonal Interactions.

Compared to peptide sequences, individual amino acids have long been identified as unfavorable candidates in fabricating functional helical structures from atomic to nanoscale due to the deficient H-bonding sites, thus limiting their applications such as optics and chiral sensing. By modified fused aryl groups at N -terminal, we found amino acids self-assembled into helical structures at atomic-level that could be incorporated into the modularized, ternary coassembly chiral systems whose supramolecular chirality and chiroptical properties including circularly polarized light absorption and luminescence were precisely programmed. In the solid-states, N -terminal aryl amino acids (alanine and phenylglycine) appended with pyrene segments self-assembled into α-helix-like structures induced by asymmetrical H-bonds between carboxylic acid and amide segments, further inducing supramolecular tilted chirality of achiral aryl groups. These building units were capable of binding melamine and electron deficient building block via duplex H-bonds and charge-transfer interactions in an orthogonal way. Complexation in binary coassemblies arouses significant chiroptical variations. Charge-transfer interaction enhances the dissymmetry g-factor of absorption (g abs ) by 1~2 order of magnitudes (up to 1.4×10 -2 ) with extended Cotton effect active region (from 250 nm to 600 nm). Incorporating melamine pronouncedly inverts the handedness of circularly polarized luminescence, and selectively boosts the dissymmetry g-factor (g lum ). Melamine also induced the emergence of macroscopic chirality at nanoscale, whereby two dimensional lamellar structures from aryl amino acids are transformed into one dimensional helices at nanoscale. Exclusively, aryl phenylglycine synergistically integrate melamine and charge-transfer species into ternary component complexes, which self-assembled into giant tubular structures at microscale via helical scrolling process.