Table S1. Elemental mass percentage (wt%) of CNCs and A-CNCs obtained from elemental analysis and DSS calculated from mass percentage of N element.

Figure S1. Illustrative strategy for preparing alkynylated cellulose nanocrystals.

Figure S2. FTIR spectra of CNCs and A-CNCs with KBr as tablet.

Figure S3. TEM images of (A) CNCs and (B) A-CNCs.

Figure S4. GPC chromatogram of P1. Calibrated with polystyrenes, using THF as eluent, at room temperature, polymer concentration 1 mg/mL.

Figure S5. FTIR spectra of (a) silica products, (b) P1 and (c) TCPHPs with KBr as tablet.

Figure S6. SEM images of (A) TCPHPs and EDS mapping patterns of (B) C, N, O and Si, (C) carbon, (D) nitrogen, (E) oxygen and (F) silicon elements in TCPHPs.

Figure S7. SEM images of (A) PHPs and EDS mapping patterns of (B) C, N, O, Si, (C) carbon, (D) nitrogen, (E) oxygen and (F) silica in PHPs.

Figure S8. SEM images of (A) TCPHPs prepared with 0.25 mL TEOS, (A-1) pores on the surface, (A-2) pores inside; (B) TCPHPs prepared with 1.0 mL TEOS, (B-1) pores on the surface, (B-2) pores inside.

Figure S9. XPS spectra measured on the surface of (a) TCPHPs, (b) CPPs and (c) PHPs.

Figure S10. (A) CD and (B) UV–vis adsorption Spectra of CNCs and A-CNCs. Measured by dispersing the products in deionized water qualitatively.

Figure S11. (A) CD and (B) UV–vis absorption spectra of (a) P1 and (b) inorganic silica products. Polymer products were measured by dissolving the products in CHCl3 (c = 10−4 M, by monomer units). Inorganic silica products were measured by directly pressing the products between two pieces of quartz glass after swelling with CHCl3.

Figure S12. (A) CD and (B) UV–vis absorption spectra of TCPHPs measured at different angles. Samples were measured by directly pressing the products between two pieces of quartz glass after swelling with CHCl3.

Figure S13. HPLC spectrum for resolution of naproxen after being enantioselective released by TCPHPs. (Column, 25 × 0.46 cm [i.d.]; eluent, n-hexane/i-PrOH = 4/1, v/v; elution flow rate, 1.0 mL/min; UV, 273 nm).

Figure S14. (A) Accumulative release amount-time profiles of naproxen enantiomers from PHPs in ethanol, measured by UV–vis absorbance at 316 nm; (B) e.e.-time profiles of racemic naproxen from PHPs in ethanol, measured by HPLC with the mobile phase of isopropanol/n-hexane (1/4, v/v).