Rational
utilization of diverse weak forces in directing multiple-constituent
chiral coassemblies is of vital importance in fabricating functional
chiroptical materials. In this work, arene-perfluoroarene (AP) and
hydrogen bonds were orthogonally employed to afford synergistic binary
and ternary coassemblies. On the supramolecular scale, amino acids
were connected to achiral pyrene moieties, which packed into supramolecular
tilt chirality individually. The modified aromatic amino acids coassembled
with melamine and octafluoronaphthalene (OFN) through multiple hydrogen
bond and AP interactions, respectively, to construct binary and ternary
systems. The introduction of hydrogen bonds and AP interactions shall
alter the nanostructures and luminescent properties. Emergence of
macroscopic chirality at nanoscale was realized, accompanied by the
inversion of circularly polarized luminescence. These interactions
working in an orthogonal way regulated the supramolecular chirality,
emission properties, nanostructure transformation, and chiroptical
activities, which enriched the protocols in designing functional chiral
composites.