Singlet chiral photocatalysis is
highly challenging. Herein, we
report fluorescence resonance energy transfer (FRET)-based chiral
photocatalysis with γ-cyclodextrin (CD)-grafted lanthanide-doped
upconverted nanoparticles (UCNP). The CD-modified UCNP strongly emits
in the UV wavelength region upon excitation with a 980 nm laser, which
selectively sensitizes the photosubstrates complexed by CD on the
surface of UCNP through FRET. Therefore, enantiodifferentiating photocyclodimerization
of anthracene or naphthalene derivatives sensitized by the CD-modified
UCNP gives photoproducts in good enantioselectivity even in the presence
of a catalytic amount of CD-modified UCNP. Moreover, the photocatalysts
are readily separated and could be reused for at least six cycles
without decreasing the enantioselectivity.