To introduce the chiral BINOL unit into a cycloparaphenylene nanohoop, we treated enantiomerically pure MOM-protected BINOL (S)-1 with dibromide 2, a common precursor used in CPP synthesis, to close the ring by Suzuki-Miyaura cross-coupling (Fig. ). Following the macrocyclization which proceeded in 24% yield, (S)-3 was subjected to a freshly prepared solution of sodium naphthalenide to facilitate aromatization. Deprotection of the MOM groups using Amberlyst ® resin produced the macrocycle (S)-OH- [9]CPP in 52% yield over two steps as a pale yellow solid. Phosphorylation of BINOL nanohoop (S)-OH- [9]CPP with POCl3 with the subsequent hydrolysis of the intermediate phosphorus chloride yielded the final BINOLderived phosphoric acid (S)-PO4H- [9]CPP in 98% yield over the last two steps. Synthesis of the other enantiomer (R)-PO4H- [9]CPP was performed following the same procedure from the R-isomer of the BINOL boronic ester (R)-1 in similar yields (see S.I. for further details). All new compounds were fully characterized by 1 H and C NMR spectroscopy and high-resolution mass spectrometry (Supplementary Figs. 39 -59). Single crystals of nanohoop (R)-OH- [9]CPP were successfully grown by diffusion of n-hexanes into a saturated solution of the compound in 1,2-dichlorobenzene (Fig. ). Single crystal X-ray diffraction (SC-XRD) reveals that the introduction of a BINOL moiety via meta-functionalization into a cycloparaphenylene results in a structure that is relatively similar to the parent nanohoop [9]CPP. For instance, both (R)-OH-[9]CPP and [9]CPP exhibit, in the solid state, oval shape with near-identical internal cavity diameters of 12.8 Å (vs. 12.8 Å for [9]CPP) and 11.2 Å (vs. 11.3 Å), respectively. This structural similarity is possible because of the torsion angle of 73 ° within the BINOL skeleton, which is also responsible for the chirality of the nanohoop (Fig. and Supplementary Figs. ). Based on the Flack parameter we were able to confirm the absolute configuration of the nanohoop (R)-