Supplementary Materials: Development of Amyloseand β-cyclodextrin-based Chiral Fluorescent Sensors Bearing Terthienyl Pendants

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S1 of S12 Supplementary Materials: Development of Amyloseand β-cyclodextrin-based Chiral Fluorescent Sensors Bearing Terthienyl Pendants Tomoyuki Ikai, Changsik Yun, Yutaka Kojima, Daisuke Suzuki, Katsuhiro Maeda and Shigeyoshi Kanoh 1. Supporting Data Figure S1. Histogram analysis of the DLS measurements of Am-1b in THF (a) and hexane/thf (90/10, v/v) (b) at 30 C after filtration through a membrane filter with a pore size of 0.45 μm. [Glucose unit] = 1.0 10 5 M. Figure S2. CD and absorption spectra of Am-1b and Ce-1b in hexane/thf (90/10, v/v) at 25 C. [Glucose unit] = 1.0 10 5 M. (Reproduced with permission from Reference [1]. Copyright 2016 The Royal Society of Chemistry).

S2 of S12 Figure S3. CD and absorption spectra of CyD-1b in THF (blue line) and hexane/thf (90/10, v/v) (red line) at 25 C. [Glucose unit] = 1.0 10 5 M. Figure S4. Fluorescence spectra of Am-1b (a,b) and CyD-1b (c,d) upon the addition of various amounts of 5 (0 70 mm) in THF (a,c) and hexane/thf (90/10, v/v) (b,d) at room temperature. [Glucose unit] = 1.0 10 5 M, λex = 450 nm. Insets: Photographs of the corresponding solutions in the absence (left) and presence (right) of nitrobenzene (70 mm) under irradiation at 365 nm.

S3 of S12 Figure S5. Stern Volmer plots for the fluorescence quenching of Ce-1b (λex = 450 nm) by the (R)- (red) and (S)- (blue) isomers of 6 (a) and 10 (b) in hexane/thf (90/10, v/v) at room temperature. [Glucose unit] = 1.0 10 5 M. The results of the fluorescence quenching using 7a, 8, 9 and 11a as guest quenchers were reported in Reference [1]. Figure S6. Fluorescence spectra of Am-1b (a,b) and CyD-1b (c,d) in the absence (red line) and presence (blue line) of rac-7c (a,c) and rac-11c (b,d) in hexane/thf (90/10, v/v) at room temperature. [Glucose unit] = 1.0 10 5 M, λex = 450 nm.

S4 of S12 (R )-11a (S )-11a 0 10 20 30 40 50 Elution time (min) Figure S7. Chromatogram for the resolution of 11a on Am-1b-based CSP (column: 25 cm 0.20 cm (i.d.); eluent: ethanol; flow rate: 0.05 ml min 1 ).

S5 of S12 2. NMR Spectral Data 0 0.1 0.2 0.3 0.4 0.5 0.6 0.7 13.0 12.0 11.0 10.0 9.0 8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0 = Am-1a-5.jdf Sample_Id = S#395093 = PYRIDINE-D5 Creation_Time = 1-MAY-2015 11:05:10 Revision_Time = 27-AUG-2016 12:46:45 Current_Time = 27-AUG-2016 12:46:51 Dim_Units = [] Site = ECS 400 Spectrometer = JNM-ECS400 Field_Strength = 9.389766[T] (400[MHz]) X_Acq_Duration = 2.18365952[s] = 399.78219838[MHz] = 5[] X_Resolution = 0.45794685[Hz] = 7.5030012[kHz] = 399.78219838[MHz] Irr_Offset = 5[] = 399.78219838[MHz] Tri_Offset = 5[] Scans = 300 Total_Scans = 300 Recvr_Gain = 52 = 80[dC] X_90_Width = 9.4[us] X_Acq_Time = 2.18365952[s] = 0.7[dB] = 4.7[us] Dante_Presat Repetition_Time = 4.18365952[s] 10.493 9.981 7.792 7.773 7.753 7.627 7.606 7.437 7.421 7.284 7.073 5.771 5.583 5.361 4.917 4.768 4.169 Figure S8. 1 H-NMR (pyridine-d5, 400 MHz, 80 C) spectrum of Am-1a. 0 0.1 0.2 0.3 0.4 0.5 0.6 0.7 0.8 0.9 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 1.8 1.9 2.0 = Am-1b-3.jdf Sample_Id = S#514215 = CHLOROFORM-D Creation_Time = 21-AUG-2015 14:30:01 Revision_Time = 27-AUG-2016 14:02:24 Current_Time = 27-AUG-2016 14:02:45 Dim_Units = [] = 5.0[] Irr_Offset = 5.0[] Tri_Offset = 5.0[] Scans = 350 Total_Scans = 350 Recvr_Gain = 50 = 55[dC] Dante_Presat 7.848 7.625 6.788 6.735 6.522 6.468 5.507 5.104 4.489 3.912 3.401 2.661 2.613 1.601 1.249 1.228 0.854 0.843 0.829 Figure S9. 1 H-NMR (CDCl3, 500 MHz, 55 C) spectrum of Am-1b.

S6 of S12 0 0.1 0.2 0.3 0.4 0.5 0.6 0.7 2.13 0.81 2.22 6.34 2.08 2.06 0.99 1 0.97 1.94 1.18 = CyD-1a-4.jdf Sample_Id = S#730790 Creation_Time = 8-OCT-2015 20:13:27 Revision_Time = 27-AUG-2016 14:14:34 Current_Time = 27-AUG-2016 14:14:46 Dim_Units = [] = 5.0[] Irr_Offset = 5.0[] Tri_Offset = 5.0[] Scans = 69 Total_Scans = 69 Recvr_Gain = 60 = 80[dC] Dante_Presat 9.460 9.331 7.534 7.517 7.316 7.298 7.283 7.266 7.194 7.015 6.742 5.482 5.463 5.327 4.845 4.643 4.593 4.289 4.054 3.077 2.503 2.500 1.079 Figure S10. 1 H-NMR (DMSO-d6, 500 MHz, 80 C) spectrum of CyD-1a. 0 0.1 0.2 0.3 0.4 0.5 0.6 0.7 0.8 0.9 1.0 1.1 1.2 6.27 36.41 0.90 0.94 0.90 1.83 0.94 8.69 4.23 109.67 24.91 = CyD-1b-4.jdf Sample_Id = S#768398 = CHLOROFORM-D Creation_Time = 10-OCT-2015 21:27:26 Revision_Time = 27-AUG-2016 14:33:47 Current_Time = 27-AUG-2016 14:33:57 Dim_Units = [] = 5.0[] Irr_Offset = 5.0[] Tri_Offset = 5.0[] Scans = 250 Total_Scans = 250 = 55[dC] Dante_Presat 7.356 7.044 6.997 6.935 6.908 6.881 6.859 6.783 6.761 6.707 6.577 6.557 6.491 5.601 5.310 5.101 4.854 4.636 4.489 3.934 2.697 2.684 2.659 2.645 1.612 1.294 1.263 0.874 Figure S11. 1 H-NMR (CDCl3, 500 MHz, 55 C) spectrum of CyD-1b.

S7 of S12 0 1.0 2.0 3.0 4.0 5.0 1.05 1.94 1.98 2.95 2.03 3.01 = (R)-g12 DMSO -4.jdf Sample_Id = S#455299 Creation_Time = 1-JUL-2016 12:19:47 Revision_Time = 27-AUG-2016 10:28:57 Current_Time = 27-AUG-2016 10:29:07 Dim_Units = [] = 5.0[] Irr_Offset = 5.0[] Tri_Offset = 5.0[] Scans = 16 Total_Scans = 16 Recvr_Gain = 46 = 20.7[dC] Dante_Presat 9.585 9.572 8.326 8.308 8.145 8.127 7.498 7.484 7.414 7.399 7.389 5.694 5.680 3.673 Figure S12. 1 H-NMR (DMSO-d6, 500 MHz, rt) spectrum of (R)-6. 0 0.1 0.2 0.3 0.4 0.5 0.6 0.7 0.8 0.9 1.0 210.0200.0190.0180.0170.0160.0150.0140.0130.0120.0110.0100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0 0-10.0-20.0 sexp( 2.0[Hz], 0.0[s] ) = (R)D-g12 C NMR -4.jdf Experiment = single_pulse_dec Sample_Id = 111 Creation_Time = 23-JUN-2016 10:11:24 Revision_Time = 27-AUG-2016 10:50:48 Current_Time = 27-AUG-2016 10:53:56 Dim_Size = 26214 Dim_Title = 13C Dim_Units = [] X_Acq_Duration = 0.83361792[s] = 13C = 125.76529768[MHz] = 100[] X_Points = 32768 X_Prescans = 4 X_Resolution = 1.19959034[Hz] = 39.3081761[kHz] Irr_Offset = 5.0[] Scans = 411 Total_Scans = 411 = 19.8[dC] X_90_Width = 9[us] X_Acq_Time = 0.83361792[s] = 30[deg] = 6[dB] = 3[us] Irr_Atn_Dec = 22.048[dB] Irr_Atn_Noe = 22.048[dB] Irr_Noise = WALTZ Decoupling = TRUE Noe = TRUE Noe_Time = 2[s] Repetition_Time = 2.83361792[s] X : parts per Million : 13C 170.830 165.069 149.245 139.125 135.767 129.348 128.661 128.413 128.337 123.472 57.143 52.421 Figure S13. 13 C-NMR (DMSO-d6, 125 MHz, rt) spectrum of (R)-6.

S8 of S12 0 1.0 2.0 3.0 4.0 5.0 6.0 1.03 2.05 1.97 2.94 1.96 3.08 = (S)-g12 DMSO-2.jdf Sample_Id = S#603931 Creation_Time = 30-JUN-2016 16:27:21 Revision_Time = 27-AUG-2016 10:22:53 Current_Time = 27-AUG-2016 10:23:37 Dim_Units = [] = 5.0[] Irr_Offset = 5.0[] Tri_Offset = 5.0[] Scans = 16 Total_Scans = 16 Recvr_Gain = 50 = 20[dC] Dante_Presat 9.586 9.573 8.326 8.307 8.143 8.125 7.495 7.482 7.413 7.398 7.388 5.692 5.678 3.672 Figure S14. 1 H-NMR (DMSO-d6, 500 MHz, rt) spectrum of (S)-6. 0 0.1 0.2 0.3 0.4 0.5 0.6 0.7 0.8 0.9 1.0 210.0200.0190.0180.0170.0160.0150.0140.0130.0120.0110.0100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0 0-10.0-20.0 sexp( 2.0[Hz], 0.0[s] ) = (S)L-g12 C NMR-4.jdf Experiment = single_pulse_dec Sample_Id = 111 Creation_Time = 23-JUN-2016 10:38:00 Revision_Time = 27-AUG-2016 10:56:28 Current_Time = 27-AUG-2016 10:56:46 Dim_Size = 26214 Dim_Title = 13C Dim_Units = [] X_Acq_Duration = 0.83361792[s] = 13C = 125.76529768[MHz] = 100[] X_Points = 32768 X_Prescans = 4 X_Resolution = 1.19959034[Hz] = 39.3081761[kHz] Irr_Offset = 5.0[] Scans = 455 Total_Scans = 455 = 19.7[dC] X_90_Width = 9[us] X_Acq_Time = 0.83361792[s] = 30[deg] = 6[dB] = 3[us] Irr_Atn_Dec = 22.048[dB] Irr_Atn_Noe = 22.048[dB] Irr_Noise = WALTZ Decoupling = TRUE Noe = TRUE Noe_Time = 2[s] Repetition_Time = 2.83361792[s] X : parts per Million : 13C 170.814 165.053 149.229 139.109 135.751 129.332 128.645 128.397 128.321 123.456 57.127 52.405 Figure S15. 13 C-NMR (DMSO-d6, 125 MHz, rt) spectrum of (S)-6.

S9 of S12 3.78 3.66 3.93 0 1.0 2.0 3.0 4.0 0.88 2.84 1.95 1.97 = (D)-g15 DMSO-3.jdf Sample_Id = S#507921 Creation_Time = 8-FEB-2016 13:52:52 Revision_Time = 27-AUG-2016 12:38:40 Current_Time = 27-AUG-2016 12:38:45 Dim_Units = [] = 5.0[] Irr_Offset = 5.0[] Tri_Offset = 5.0[] Scans = 16 Total_Scans = 16 Recvr_Gain = 60 = 80[dC] Dante_Presat 8.840 8.826 8.548 8.280 8.263 8.257 8.240 8.089 8.071 8.038 8.021 4.513 4.502 4.487 3.673 3.336 3.323 3.311 3.297 1.907 1.898 1.880 1.869 1.635 1.622 1.608 1.596 1.484 1.468 Figure S16. 1 H-NMR (DMSO-d6, 500 MHz, 80 C) spectrum of (R)-10. 0 0.1 0.2 0.3 0.4 0.5 0.6 0.7 0.8 0.9 1.0 1.1 1.2 1.3 210.0200.0190.0180.0170.0160.0150.0140.0130.0120.0110.0100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0 0-10.0-20.0 sexp( 2.0[Hz], 0.0[s] ) = (D)-g15 C NMR -4.jdf Experiment = single_pulse_dec Sample_Id = 111 Creation_Time = 23-JUN-2016 16:13:19 Revision_Time = 27-AUG-2016 11:02:46 Current_Time = 27-AUG-2016 11:03:03 Dim_Size = 26214 Dim_Title = 13C Dim_Units = [] X_Acq_Duration = 0.83361792[s] = 13C = 125.76529768[MHz] = 100[] X_Points = 32768 X_Prescans = 4 X_Resolution = 1.19959034[Hz] = 39.3081761[kHz] Irr_Offset = 5.0[] Scans = 473 Total_Scans = 473 = 20.5[dC] X_90_Width = 9[us] X_Acq_Time = 0.83361792[s] = 30[deg] = 6[dB] = 3[us] Irr_Atn_Dec = 22.048[dB] Irr_Atn_Noe = 22.048[dB] Irr_Noise = WALTZ Decoupling = TRUE Noe = TRUE Noe_Time = 2[s] Repetition_Time = 2.83361792[s] X : parts per Million : 13C 172.464 165.062 164.462 149.133 148.857 140.234 139.242 128.979 128.617 123.504 123.447 52.768 51.986 39.099 30.028 28.388 23.104 Figure S17. 13 C-NMR (DMSO-d6, 125 MHz, rt) spectrum of (R)-10.

S10 of S12 0 1.0 2.0 3.0 4.0 1.03 0.89 3.83 4.06 2.86 2.05 1.97 3.89 = (L)-g15 DMSO-3.jdf Sample_Id = S#311769 Creation_Time = 5-FEB-2016 08:26:06 Revision_Time = 27-AUG-2016 12:37:46 Current_Time = 27-AUG-2016 12:37:50 Dim_Units = [] = 5.0[] Irr_Offset = 5.0[] Tri_Offset = 5.0[] Scans = 16 Total_Scans = 16 Recvr_Gain = 62 = 80[dC] Dante_Presat 8.839 8.824 8.550 8.280 8.261 8.257 8.239 8.089 8.071 8.038 8.021 4.532 4.517 4.503 3.673 3.337 3.323 3.311 3.298 1.907 1.880 1.869 1.637 1.622 1.610 1.598 1.483 1.469 1.453 Figure S18. 1 H-NMR (DMSO-d6, 500 MHz, 80 C) spectrum of (S)-10. 0 0.1 0.2 0.3 0.4 0.5 0.6 210.0200.0190.0180.0170.0160.0150.0140.0130.0120.0110.0100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0 0-10.0-20.0 sexp( 2.0[Hz], 0.0[s] ) = (L)-g15 C NMR -4.jdf Experiment = single_pulse_dec Sample_Id = 111 Creation_Time = 23-JUN-2016 15:45:44 Revision_Time = 27-AUG-2016 11:04:00 Current_Time = 27-AUG-2016 11:05:01 Dim_Size = 26214 Dim_Title = 13C Dim_Units = [] X_Acq_Duration = 0.83361792[s] = 13C = 125.76529768[MHz] = 100[] X_Points = 32768 X_Prescans = 4 X_Resolution = 1.19959034[Hz] = 39.3081761[kHz] Irr_Offset = 5.0[] Scans = 532 Total_Scans = 532 Recvr_Gain = 56 = 20.4[dC] X_90_Width = 9[us] X_Acq_Time = 0.83361792[s] = 30[deg] = 6[dB] = 3[us] Irr_Atn_Dec = 22.048[dB] Irr_Atn_Noe = 22.048[dB] Irr_Noise = WALTZ Decoupling = TRUE Noe = TRUE Noe_Time = 2[s] Repetition_Time = 2.83361792[s] X : parts per Million : 13C 172.483 165.091 164.490 149.153 148.876 140.244 139.261 128.998 128.636 123.523 123.466 52.787 52.014 39.166 30.038 28.407 23.113 Figure S19. 13 C-NMR (DMSO-d6, 125 MHz, rt) spectrum of (S)-10.

S11 of S12 0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 9.0 10.0 4.00 10.10 2.18 1.97 2.00 = (R)-G4-2.jdf Sample_Id = S#839263 = CHLOROFORM-D Creation_Time = 24-NOV-2015 22:57:50 Revision_Time = 27-AUG-2016 12:26:16 Current_Time = 27-AUG-2016 12:26:32 Dim_Units = [] Site = ECS 400 Spectrometer = JNM-ECS400 Field_Strength = 9.389766[T] (400[MHz]) X_Acq_Duration = 2.18365952[s] = 399.78219838[MHz] = 5[] X_Resolution = 0.45794685[Hz] = 7.5030012[kHz] = 399.78219838[MHz] Irr_Offset = 5[] = 399.78219838[MHz] Tri_Offset = 5[] Scans = 32 Total_Scans = 32 Recvr_Gain = 46 = 20[dC] X_90_Width = 9.4[us] X_Acq_Time = 2.18365952[s] = 0.7[dB] = 4.7[us] Dante_Presat Repetition_Time = 4.18365952[s] 8.117 8.095 7.970 7.899 7.782 7.761 7.411 7.409 7.329 7.259 6.770 6.766 6.752 6.747 Figure S20. 1 H-NMR (CDCl3, 400 MHz, rt) spectrum of (R)-11c. 0 0.1 0.2 0.3 0.4 0.5 0.6 0.7 0.8 0.9 1.0 1.1 1.2 1.3 1.4 1.5 1.6 220.0210.0200.0190.0180.0170.0160.0150.0140.0130.0120.0110.0100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0 0-10.0-20.0 sexp( 2.0[Hz], 0.0[s] ) = (R)-G4 C NMR-4.jdf Experiment = single_pulse_dec Sample_Id = 111 = CHLOROFORM-D Creation_Time = 22-JUN-2016 09:35:36 Revision_Time = 27-AUG-2016 10:58:25 Current_Time = 27-AUG-2016 10:59:03 Dim_Size = 26214 Dim_Title = 13C Dim_Units = [] X_Acq_Duration = 0.83361792[s] = 13C = 125.76529768[MHz] = 100[] X_Points = 32768 X_Prescans = 4 X_Resolution = 1.19959034[Hz] = 39.3081761[kHz] Irr_Offset = 5.0[] Scans = 1000 Total_Scans = 1000 = 20.4[dC] X_90_Width = 9[us] X_Acq_Time = 0.83361792[s] = 30[deg] = 6[dB] = 3[us] Irr_Atn_Dec = 22.048[dB] Irr_Atn_Noe = 22.048[dB] Irr_Noise = WALTZ Decoupling = TRUE Noe = TRUE Noe_Time = 2[s] Repetition_Time = 2.83361792[s] X : parts per Million : 13C 164.360 133.647 133.351 131.920 131.415 130.232 129.240 128.229 127.838 127.285 126.312 126.207 124.022 123.498 121.361 Figure S21. 13 C-NMR (CDCl3, 125 MHz, rt) spectrum of (R)-11c.

S12 of S12 0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 9.0 4.06 10.34 2.15 1.97 2.00 = (S)-G4-4.jdf Sample_Id = S#327769 = CHLOROFORM-D Creation_Time = 26-NOV-2015 08:57:05 Revision_Time = 27-AUG-2016 10:37:12 Current_Time = 27-AUG-2016 10:37:27 Dim_Units = [] = 5.0[] Irr_Offset = 5.0[] Tri_Offset = 5.0[] Scans = 32 Total_Scans = 32 = 19.9[dC] Dante_Presat 8.115 8.096 7.989 7.973 7.921 7.905 7.779 7.762 7.503 7.491 7.475 7.428 7.413 7.343 7.329 7.259 6.765 6.750 Figure S22. 1 H-NMR (CDCl3, 500 MHz, rt) spectrum of (S)-11c. 0 0.1 0.2 0.3 0.4 0.5 0.6 0.7 0.8 0.9 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 1.8 1.9 2.0 220.0210.0200.0190.0180.0170.0160.0150.0140.0130.0120.0110.0100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0 0-10.0-20.0 sexp( 2.0[Hz], 0.0[s] ) = (S)-G4 C NMR -4.jdf Experiment = single_pulse_dec Sample_Id = 111 = CHLOROFORM-D Creation_Time = 22-JUN-2016 17:32:24 Revision_Time = 27-AUG-2016 10:59:55 Current_Time = 27-AUG-2016 11:00:15 Dim_Size = 26214 Dim_Title = 13C Dim_Units = [] X_Acq_Duration = 0.83361792[s] = 13C = 125.76529768[MHz] = 100[] X_Points = 32768 X_Prescans = 4 X_Resolution = 1.19959034[Hz] = 39.3081761[kHz] Irr_Offset = 5.0[] Scans = 848 Total_Scans = 848 = 21.2[dC] X_90_Width = 9[us] X_Acq_Time = 0.83361792[s] = 30[deg] = 6[dB] = 3[us] Irr_Atn_Dec = 22.048[dB] Irr_Atn_Noe = 22.048[dB] Irr_Noise = WALTZ Decoupling = TRUE Noe = TRUE Noe_Time = 2[s] Repetition_Time = 2.83361792[s] X : parts per Million : 13C 164.340 146.532 133.627 133.341 131.910 131.414 130.231 129.230 128.228 127.284 126.311 126.197 124.003 123.488 121.351 Figure S23. 13 C-NMR (CDCl3, 125 MHz, rt) spectrum of (S)-11c. Reference 1. Ikai, T.; Suzuki, D.; Kojima, Y.; Yun, C.; Maeda, K.; Kanoh, S. Chiral fluorescent sensors based on cellulose derivatives bearing terthienyl pendants. Polym. Chem. 2016, 7, 4793 4801.

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