Supporting Information

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1 Supporting Information Enantioselective Recognition for Many Different Kinds of Chiral Guests by One Chiral Receptor Based on Tetraphenylethylene Cyclohexylbisurea Jia-Bin Xiong, a Wen-Zhao Xie, a Jian-Ping Sun, a Jin-Hua Wang, a Zhi-Hua Zhu, a Hai-Tao Feng, a Dong Guo, b Hui Zhang, b and Yan-Song Zheng * a a Key Laboratory for Chemistry of Energy Conversion and Storage Materials, Ministry of Education, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan, China. b College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 3615, China. zyansong@hotmail.com Table of Contents Materials and Methods. 1 Fig. S1. 1 H-NMR spectrum of R,R-5 in CDCl Fig. S2. 13 C-NMR spectrum of R,R-5 in CDCl Fig. S3. IR spectrum of R,R-5 3 Fig. S4. HRMS spectrum of R,R-5. 3 Fig. S5. 1 H-NMR spectrum of S,S-5 in CDCl Fig. S6. 13 C-NMR spectrum of S,S-5 in CDCl Fig. S7. IR spectrum of S,S-5. 5 Fig. S8. HRMS spectrum of S,S Fig. S9. CD spectra of (S,S)-5 in 1,2-dichloroethane at various concentration. 6 Fig. S1. The fluorescence spectra of the mixture of analyte enantiomer and (R,R) Fig. S11. Job plot for 1 H NMR titration of (R,R)-5 (.3 M) with S-6 in CDCl 3. 9 Fig. S12. Job plot for 1 H NMR titration of (R,R)-5 (.3 M) with R-6 in CDCl 3 9 Fig. S13. Chemical shift of the β-methylene protons with concentration of S-6 added. 1 Fig. S14. Chemical shift of the β-methylene protons with concentration of R-6 added 1 Materials and Methods Materials. All reagents and solvents were chemical pure (CP) grade or analytical reagent (AR) grade and were used as received unless otherwise indicated. CDCl 3 for NMR solvent was stirred for 2 min over anhydrous K 2 CO 3 before used. Measurements. 1 H NMR and 13 C NMR spectra were measured onspectrometer at 298 K in CDCl 3. Fluorescent emission spectra were collected on fluorophotometer at 298 K. Field emission scanning electron microscopy (FE-SEM) images were taken on electron microscope operating at 5 kv or 1 kv. Transmission electron micrographs (TEM) were recorded on electron microscope at 2 kv. The gel diluted with hexane and the suspension was dropped onto a copper grid covered with a thin carbon film on a filter paper and air dried. Infrared spectra were recorded on spectrometer. 1

2 Mass spectrum was measured on FTMS instrument. Fig. S1. 1 H-NMR spectrum of R,R-5 in CDCl 3. Fig. S2. 13 C-NMR spectrum of R,R-5 in CDCl 3. 2

3 Fig. S3. IR spectrum of R,R-5. Fig. S4.HRMS spectrum of R,R-5. 3

4 NAME XiongJB-1huanjieranqingpu# EXPNO 11 PROCNO 1 Date_ Time INSTRUM spect PROBHD 5 mm PABBO BB/ PULPROG zg3 TD SOLVENT CDCl3 NS 16 DS 1 SWH Hz FIDRES Hz AQ sec RG DW 52. usec DE 6.5 usec TE K D1 1. sec TD 1 ======== CHANNEL f1 ======== SFO MHz NUC1 1H P usec SI SF MHz WDW EM SSB LB.3 Hz GB PC ppm Fig. S5. 1 H-NMR spectrum of S,S-5 in CDCl NAME XiongJB-huanjierantanpu# EXPNO 21 PROCNO 1 Date_ Time 19.2 INSTRUM spect PROBHD 5 mm PABBO BB/ PULPROG zgpg3 TD SOLVENT CDCl3 NS 248 DS 4 SWH Hz FIDRES Hz AQ sec RG DW 17.6 usec DE 6.5 usec TE K D1 2. sec D11.3 sec TD 1 ======== CHANNEL f1 ======== SFO MHz NUC1 13C P1 1. usec SI SF MHz WDW EM SSB LB 1. Hz GB PC ppm Fig. S6. 13 C-NMR spectrum of S,S-5 in CDCl 3. 4

5 Fig. S7. IR spectrum of S,S-5. Fig. S8. HRMS spectrum of S,S-5. 5

6 4 CD (mdeg) X1-3 M 1X1-3 M 5X1-4 M 1X1-4 M 5X1-5 M Fig. S9. CD spectra of (S,S)-5 in 1,2-dichloroethane at various concentration. A 2 1 R-2-chloromandelic acid 6 S-2-chloromandelic acid 6 B R-mandelic acid 7 S-mandelic acid C R-1,2,3,4-tetrahydro-2-naphthoic acid 8 S-1,2,3,4-tetrahydro-2-naphthoic acid 8 D 2 D-dibenzoyltartaric acid 9 L-dibenzoyltartaric acid

7 E D-ditoluoyltartaric acid 1 L-ditoluoyltartaric acid 1 F 4 2 D-camphorsulfonic acid 11 L-camphorsulfonic acid G 6 R-phenylglycinol 12 S-phenylglycinol 12 H R,R-diphenylethylenediamine 13 S,S-diphenylethylenediamine I S,S-1,2-cyclohexanediamine 14 R,R-1,2-cyclohexanediamine 14 J D-Leu 15 L-Leu K 2 1 D-Phe 16 L-Phe 16 L 2 1 L-Trp 17 D-Trp

8 M D-Pro 18 L-Pro 18 N D-Thr 19 L-Thr wavelength (nm) O D-Arg 2 L-Arg 2 P D-His 21 L-His Q L-Menthol 22 D-Menthol 22 R 4 2 R-binol 23 S-binol S R-methylmandelate 24 S-methylmandelate 24 T D-diethyltartrate 25 L-diethyltartrate

9 Fig. S1. The fluorescence spectra of the mixture of analyte enantiomer and (R,R)-5 in different solvents. (A) M in hexane/1,2-dichloroethane 3.5:1. (B) M in hexane/1,2-dichloroethane 2.7:1. (C) M in hexane/1,2-dichloroethane 4.:1. (D) M in hexane/ 1,2-dichloroethane 5.5:1. (E) M in hexane/1,2-dichloroethane 4.:1. (F) M in hexane/1,2-dichloroethane 5.9:1. (G) M in hexane/1,2-dichloroethane 4.:1. (H) M in hexane/1,2-dichloroethane 3.9:1. (I) M in hexane/1,2-dichloroethane 6.:1. (J) M in H 2 O/THF 4.:1. (K) M in H 2 O/THF 1.6:1. (L) M in H- 2O/THF 1.9:1. (M) M in H 2 O/THF 1.4:1. (N) M in H 2 O/THF 1.7:1. (O) M in H 2 O/THF 1.6:1. (P) M in H 2 O/THF 1.5:1. (Q) M in H 2 O/THF 1.7:1. (R) M in H 2 O/THF 1.9:1. (S) M in hexane/1,2-dichloroethane 3.6:1. (T) M in hexane/1,2-dichloroethane 4.:1. [(R,R)-5] = [enantiomer of the analyte]..18 δx[r,r-5]/([r,r-5]+[s-6]) [S-6]/[R,R-5] Fig. S11. Job plot for 1 H NMR titration of (R,R)-5 (.3 M) with S-6 in CDCl δx[r,r-5]/([r,r-5]+[r-6]) [R-6]/[R,R-5] Fig. S12. Job plot for 1 H NMR titration of (R,R)-5 (.3 M) with R-6 in CDCl 3. 9

10 R^2 =.9992 K ± c ±.1127 δ (ppm) [S-6] (M) Fig. S13. Chemical shift of the β-methylene protons in cyclohexyl unit of (R,R)-5 (.3 M) with concentration of S-6 added. The red line is the fitting one R^2 = K ± c ±.4567 δ (ppm) [R-6] (M) Fig. S14. Chemical shift of the β-methylene protons in cyclohexyl unit of (R,R)-5 (.3 M) with concentration of R-6 added. The red line is the fitting one. 1