Scheme S1 Synthesis of 1-Ph and 2-Ph

Figure S1 Laser Raman spectra of poly(1-Ph) (A) and poly(2-Ph) (B) in the solid state at room temperature

Figure S2 Time-dependent ICD intensity (|∆ɛ2nd|) changes of poly(1-Ph) (A) and poly(2-Ph) (B) with (R)-PEA in toluene ((R)-PEA/toluene = 10/90 (i) and 20/80 (ii), v/v) at 25 °C. [Polymer] = 1.0 mM (calculated based on the monomer units)

Figure S3 CD titration curves (|∆ɛ2nd|) of poly(1-Ph) (A) and poly(2-Ph) (B) with (R)-PEA in toluene measured at 25 °C after allowing to stand at 25 °C for 48 h. [Polymer] = 1.0 mM

Figure S4 1H NMR spectra of poly(1-Ph) (A–C) and poly(2-Ph) (D–F) in the presence of (R)-PEA (A,D) ([PEA]/[monomer units of polymer] = 0.2–0.3), the isolated polymers ((P)-h-poly(1-Ph) (B) and (P)-h-poly(2-Ph) (E)) with static helicity memory, and the redissolved polymers ((P)-hpoly(1-Ph) (C) and (P)-h-poly(2-Ph) (F)) with static helicity memory recovered from silica gel, measured in CDCl3 at 50 °C

Figure S5 Plots of the time-dependent CD intensity changes (CDt/CD0) of poly(1-Ph) (i; l = 383 nm), poly(2-Ph) (ii; l = 378 nm), poly(1-Bu) (iii; l = 382 nm), and poly(2-Bu) (iv; l = 376 nm) measured in toluene at −10 (A) and 25 (B) °C. CD0 represents the initial CD intensity of each polymer in toluene at −10 °C. [Polymer] = ca. 1 mM. The data of poly(1-Bu) and poly(2-Bu) are cited from ref. S2

Figure S6 CD and absorption spectra of poly(1-Ph) (A) and poly(2-Ph) (B) measured in (R)-PEA/toluene (10/90, v/v) at −10 °C after allowing to stand at 25 °C for 48 h (i) and those of the recovered polymers ((P)-h-poly(1-Ph) and (P)-h-poly(2-Ph)) with static helicity memory from silica gel, measured in toluene at −10 °C (ii)

Figure S7 HPLC chromatograms for the resolutions of C (i,iii) and K (ii,iv) on the (P)-h-poly(1-Ph)-based CSP with static helicity memory at 0 °C under reversed-phase conditions before and after allowing the column filled with methanol to stand at ca. 0 °C for 2 weeks. Eluent: methanol (i,iii) or ethanol (ii,vi).

Figure S8 1H NMR (500 MHz, CDCl3, 25 °C) spectrum of 1-Ph

Figure S9 13C NMR (126 MHz, CDCl3, 25 °C) spectrum of 1-Ph

Figure S10 1H NMR (500 MHz, CDCl3, 25 °C) spectrum of 2-Ph

Figure S11 13C NMR (126 MHz, CDCl3, 25 °C) spectrum of 2-Ph

Figure S12 1H NMR (500 MHz, CDCl3, 50 °C) spectrum of poly(1-Ph)

Figure S13 1H NMR (500 MHz, CDCl3, 50 °C) spectrum of poly(2-Ph)