Supporting Information. KF and CsF Recognition and Extraction by a. Calix[4]crown-5 Strapped Calix[4]pyrrole. Multitopic Receptor
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1 Supporting Information For KF and CsF Recognition and Extraction by a Calix[4]crown-5 Strapped Calix[4]pyrrole Multitopic Receptor Sung Kuk Kim, Vincent M. Lynch, Neil J. Young, Benjamin P. Hay, *, Chang-Hee Lee, *, Jong Seung Kim, *, Bruce A. Moyer, *, and Jonathan L. Sessler, *,,# Department of Chemistry and Biochemistry, 105 E. 24th Street, Stop A5300, The University of Texas at Austin, Austin, Texas , Department of Chemistry, Kangwon National University, Chun-Chon , Korea, Department of Chemistry, Korea University, Seoul , Korea, Chemical Sciences Division, Oak Ridge National Laboratory, Oak Ridge, TN , and # Department of Chemistry, Yonsei University, Seoul , Korea Corresponding Authors: sessler@cm.utexas.edu; haybp@ornl.gov; chhlee@kangwon.ac.kr; moyerba@ornl.gov; jongskim@korea.ac.kr S1
2 Scheme S1. Synthesis of cation receptor 5 S2
3 All solvents and chemicals used were purchased from Aldrich, TCI, and Acros and used without further purification. Compound 6 was prepared as reported previously. 1 NMR spectra were recorded on a Varian Mercury 400 instrument. The NMR spectra were referenced to solvent and the spectroscopic solvents were purchased from either Cambridge Isotope Laboratories or Aldrich. Chemical ionization (CI) and electrospray ionization (ESI) mass spectra were recorded on a VG ZAB-2E instrument and a VG AutoSpec apparatus, respectively. TLC analyses were carried out using Sorbent Technologies silica gel (200 mm) sheets. Column chromatography was performed on Sorbent silica gel 60 (40 63 mm). For microcalorimetric titrations, a MicroCal VP-ITC instrument was employed. Compound 7 Calix[4]arene (4.66 g, 11.0 mmol), compound 6 1 (7.35 g, 22.0 mmol) and K 2 CO 3 (1.59 g, 11.5 mmol) were mixed in 125 ml of acetonitrile and then heated at reflux under a nitrogen atmosphere for 24 hrs. After allowing the reaction mixture to cool to RT, the acetonitrile was removed in vacuo. To the resulting white solid, CH 2 Cl 2 (100 ml) and water (100 ml) were added, and the organic layer was separated off and washed three times with 100 ml of water. The organic layer was then dried over anhydrous MgSO 4 and the solvent was evaporated in vacuo to give a white solid. Recrystallization from a mixture of dichloromethane and methanol (1/9), following column chromatography over silica gel (eluent: ethyl acetate/hexane (1/3)), gave 3.63 g (44% yield) of 6 as a white solid. 1 H NMR (400 MHz, CDCl 3 ): δ 7.93 (d, 4H, ArH, J = 8.81 Hz), 7.89 (s, 2H, ArOH), 7.06 (d, 4H, ArH, J = 7.61 Hz), (m, 6H, ArH), 6.78 (t, 2H, ArH, J = 7.61 Hz), 6.66 (t, 2H, ArH, J = 7.61 Hz), 4.39 (d, 4H, ArCH 2 Ar, J = 12.8 Hz), 4.30 (s, 8H, ArOCH 2 CH 2 OAr, J = 5.60), 3.38 (d, 4H, ArCH 2 Ar, J = 12.8 Hz), 2.57 (s, 6H, ArCOCH 3 ). 13 C NMR (100 MHz, CDCl 3 ): δ 197.2, 162.6, 153.3, 151.7, 133.7, 130.9, 130.8, 129.3, 128.7, S3
4 128.3, 125.9, 119.4, 114.7, 73.9, 66.9, 31.5, HRMS (ESI) m/z (M + Na) + calcd for C 48 H 44 NaO 8, found Compound 5 Compound 7 (0.1 g, 0.13 mmol), tetraethylene glycol ditosylate (0.07 g, 0.13 mmol) and Cs 2 CO 3 (0.13 g, 0.40 mmol) were dissolved in 30 ml of acetonitrile under a nitrogen atmosphere. After heating at reflux for 12 hours and then allowing to cool, the acetonitrile was removed in vacuo. To the resulting white solid, CH 2 Cl 2 (50 ml) and 5% aqueous HCl (100 ml) were added. The organic layer was separated off and washed three times with 50 ml of water. The organic layer was dried over anhydrous MgSO 4 and the solvent was evaporated in vacuo to give a white solid. Column chromatography over silica gel (eluent: methylene chloride/methanol (9/1)), followed by recrystallization from methanol, gave 0.03 g (23% yield) of 5 as a white solid. 1 H NMR (400 MHz, CDCl 3 ): δ 7.82 (d, 4H, ArH, J = 8.41 Hz), 7.14 (d, 4H, ArH, J = 7.61 Hz), 7.07 (d, 4H, ArH, J = 7.61 Hz), 6.93 (t, 2H, ArH, J = 7.61 Hz), (m, 6H, ArH), 3.91 (s, 8H, ArCH 2 Ar), (m, 12H, OCH 2 CH 2 O), 3.52 (t, 4H, OCH 2 CH 2 O, J = 5.20 Hz), 3.47 (t, 4H, OCH 2 CH 2 O, J = 6.80 Hz), 3.16 (t, 4H, OCH 2 CH 2 O, J = 6.40 Hz), 2.51 (s, 6H, ArCOCH 3 ). 13 C NMR (100 MHz, CDCl 3 ): δ 196.9, 162.7, 156.7, 156.1, 134.6, 134.2, 130.8, 130.5, 129.8, 129.6, 123.3, 122.9, 114.2, 73.1, 71.0, 70.0, 68.6, 68.2, 66.9, 38.3, HRMS (ESI) m/z (M + NH 4 ) + calcd for C56H62NO11, found S4
5 O O O O O O O O O O O O F - O O O O slow O O H N H H N N H N H N F - H H N N H N (a) 1 only (b) 0.28 equiv (c) 0.79 equiv (d) 1.25 equiv (e) 3.00 equiv Figure S1. Partial 1 H NMR spectra recorded during the titration of receptor 1 with TBAF (tetrabutylammonium fluoride) in CDCl 3. S5
6 (a) 1 only (b) TBACl (5 equiv) (c) TBANO 3 (5 equiv) (d) TBAClO 4 (5 equiv) ppm Figure S2. 1 H NMR spectra of (a) 1 only, (b) equiv of TBACl (tetrabutylammonium chloride), (c) equiv of TBANO 3 (tetrabutylammonium nitrate), and (d) equiv of TBAClO 4 (tetrabutylammonium perchlorate) in CDCl 3. S6
7 Table S1. ITC titration data for receptors 1-3 measured at 298 K. Estimated error 15%. a TEAF = tetraethylammonium fluoride. b 10% (v/v). c From literature. 1 d From literature. 2 host solvent guest a H T S G K a (kj/mol) (kj/mol) (kj/mol) (M -1 ) 1 CH 3 CN TEAF CH 3 OH/CHCl 3 b 2 c CH 3 OH/CHCl 3 b 3 d CH 3 OH/CHCl 3 b CsF CsF CsF S7
8 Figure S3. ITC plots showing the titrations of receptor 1 (0.20 mm) with TEAF (2.97 mm) in CH 3 CN. S8
9 (a) 1 only (b) KClO 4 (c) KF (1.0 equiv) (d) KF (2.0 equiv) ppm Figure S4. Partial 1 H NMR spectra of (a) 1 only, (b) 1 with 4.0 equiv of KClO 4, (c) 1 with 1.0 equiv of KF, and (d) 1 with 2.0 equiv of KF in CD 3 OD/CDCl 3 (1:9, v/v). S9
10 (a) 1 only H d H b H c,f NH H e H a Pyrrolic CH (b) CsClO 4 NH H b H e,f (c) CsF H d H c H a ppm Figure S5. Partial 1 H NMR spectra of (a) 1 only, (b) 1 with 4.0 equiv of CsClO 4, and (c) 1 with 4.0 equiv of CsF in CD 3 OD/CDCl 3 (1:9, v/v). S10
11 (a) 1 only (b) TBAF (5.0 equiv) ppm Figure S6. Partial 1 H NMR spectra of (a) 1 only, and (b) 1 with 5 equiv of TBAF (tetrabutylammonium fluoride) in CD 3 OD/CDCl 3 (1:9, v/v). S11
12 (a) 1 only H d Hb H c,f NH H e H a Pyrrolic CH (b) 0.72 equiv (c) 1.05 equiv (d) 1.38 equiv (e) 4.58 equiv H b H d H c H e,f H a NH Pyrrolic CH ppm Figure S7. Partial 1 H NMR spectra recorded during the titration of receptor 1 with CsF in CD 3 OD/CDCl 3 (1:9, v/v). S12
13 Figure S8. ITC plots showing the results of titrating receptor 1 (0.19 mm) with CsF (2.95 mm) in CH 3 OH/CHCl 3 (1/9, v/v). S13
14 (a) (b) ppm Figure S9. Partial 1 H NMR spectra of nitrobenzene-d 5 solutions of (a) free 1, and (b) its KF complex, which was obtained as a precipitant from 10% CD 3 OD in CDCl 3 as described in the text proper. S14
15 (a) 1 only (b) KF (c) CsF ppm Figure S10. Partial 1 H NMR spectra of nitrobenzene-d 5 solutions of 1 after exposure to (a) an ion-free aqueous D 2 O solution, (b) an aqueous D 2 O solution containing KF (5 equiv), and (c) an aqueous D 2 O solution containing CsF (5 equiv). S15
16 10.92 Å 5.62 Å 3.69 Å 2.77 Å 2 CsF 3 CsF 4 CsF Å Å 1 CsF 1 KF Figure S11. Limiting binding modes observed for the CsF or KF ion pair complexes of receptors 1 4 as inferred from X-ray diffraction analyses. Also shown are the distances between the Cs + or K + and F ions as determined from diffraction analyses for these complexes. The structures of the CsF complexes of 2, 3, and 4 were reported in Supplementary References 2, 3, and 4, respectively. S16
17 (a) 5 only (b) KF ppm Figure S12. Partial 1 H NMR spectra of nitrobenzene-d 5 solutions of 5 after contacting with (a) an ion-free aqueous D 2 O solution and (b) an aqueous D 2 O solution containing KF (5 equiv). S17
18 (a) 4 only (b) KF ppm Figure S13. Partial 1 H NMR spectra of nitrobenzene-d 5 solutions of 4 after contacting with (a) an ion-free aqueous D 2 O solution and (b) an aqueous D 2 O solution containing KF (5 equiv). S18
19 (a) (b) KF ppm Figure S14. Partial 1 H NMR spectra of nitrobenzene-d 5 solutions of a mixture of 4 and 5 after contacting with (a) an ion-free aqueous D 2 O solution and (b) an aqueous D 2 O solution containing KF (5 equiv). S19
20 X-ray Experimental for 1 KF (CH 3 OH) 3 Crystals were grown as colorless prism by slow evaporation from a mixture of chloroform and methanol. The data were collected on a Rigaku R-Axis Spider diffractometer with an image plate detector using a graphite monochromator with CuKα radiation (λ = Å). A total of 144 images of data were collected using ω-scans with a scan range of 5 and a counting time of 360 seconds per image. The data were collected at 100 K using a Rigaku XStream low temperature device. Details of crystal data, data collection and structure refinement are listed in Table S3. Data reduction were performed using the Rigaku Americas Corporation s Crystal Clear version The structure was solved by direct methods using SIR97 6 and refined by full-matrix least-squares on F 2 with anisotropic displacement parameters for the non- H atoms using SHELXL The hydrogen atoms were calculated in ideal positions with isotropic displacement parameters set to 1.2 Ueq of the attached atom (1.5 Ueq for methyl hydrogen atoms). The function, Σw( F o 2 - F c 2 ) 2, was minimized, where w = 1/[(σ(F o )) 2 + (0.0654*P) 2 + ( *P)] and P = ( F o F c 2 )/3. R w (F 2 ) refined to 0.278, with R(F) equal to and a goodness of fit, S, = Definitions used for calculating R(F), R w (F 2 ) and the goodness of fit, S, are given below. 8 The data were checked for secondary extinction effects but no correction was necessary. Neutral atom scattering factors and values used to calculate the linear absorption coefficient are from the International Tables for X-ray Crystallography (1992). 9 All figures were generated using SHELXTL/PC. 10 Further details of this structure may be obtained by consulting the relevant.cif file uploaded separately. S20
21 Table S2. Crystal data and structure refinement for 1 KF (CH 3 OH) 3. Empirical formula C81 H94 F K N4 O12 Formula weight Temperature 100(2) K Wavelength Å Crystal system Orthorhombic Space group Pnma Unit cell dimensions a = (4) Å α = 90. b = (8) Å β = 90. c = (6) Å γ = 90. Volume (9) Å 3 Z 4 Density (calculated) Mg/m 3 Absorption coefficient mm -1 F(000) 2928 Theta range for data collection 6.65 to Index ranges -43<=h<=44, -18<=k<=16, -14<=l<=15 Reflections collected Independent reflections 6945 [R(int) = ] Completeness to theta = % Absorption correction Semi-empirical from equivalents Max. and min. transmission 1.00 and Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 6945 / 12 / 472 Goodness-of-fit on F Final R indices [I>2sigma(I)] R1 = , wr2 = R indices (all data) R1 = , wr2 = Largest diff. peak and hole and e.å -3 S21
22 X-ray Experimental for 1 CsF (CH 3 OH) 2 (CHCl 3 ) 2 Crystals were grown as colorless needles by slow evaporation from chloroform and methanol. The data crystal was cut from a larger crystal and had approximate dimensions; mm. The data were collected on a Rigaku AFC12 diffractometer with a Saturn 724+ CCD using a graphite monochromator with MoKα radiation (λ = Å). A total of 650 frames of data were collected using ω-scans with a scan range of 0.5 and a counting time of 50 seconds per frame. The data were collected at 100 K using a Rigaku XStream low temperature device. Details of crystal data, data collection and structure refinement are listed in Table S5. Data reduction were performed using the Rigaku Americas Corporation s Crystal Clear version The structure was solved by direct methods using SIR97 7 and refined by full-matrix leastsquares on F 2 with anisotropic displacement parameters for the non-h atoms using SHELXL The hydrogen atoms on carbon were calculated in ideal positions with isotropic displacement parameters set to 1.2 Ueq of the attached atom (1.5 Ueq for methyl hydrogen atoms). The function, Σw( F o 2 - F c 2 ) 2, was minimized, where w = 1/[(σ(F o )) 2 + (0.0524*P) 2 + (1.4865*P)] and P = ( F o F c 2 )/3. R w (F 2 ) refined to 0.193, with R(F) equal to and a goodness of fit, S, = Definitions used for calculating R(F), R w (F 2 ) and the goodness of fit, S, are given below. 8 The data were checked for secondary extinction effects but no correction was necessary. Neutral atom scattering factors and values used to calculate the linear absorption coefficient are from the International Tables for X-ray Crystallography (1992). 9 All figures were generated using SHELXTL/PC. 10 Further details of this structure may be obtained by consulting the relevant.cif file uploaded separately. S22
23 Table S3. Crystal data and structure refinement for 1 CsF (CH 3 OH) 2 (CHCl 3 ) 2. Empirical formula C82 H92 Cl6 Cs F N4 O11 Formula weight Temperature 100(2) K Wavelength Å Crystal system Orthorhombic Space group Pbca Unit cell dimensions a = (13) Å α = 90. b = (16) Å β = 90. c = (16) Å γ = 90. Volume (16) Å 3 Z 8 Density (calculated) Mg/m 3 Absorption coefficient mm -1 F(000) 6928 Crystal size mm Theta range for data collection 2.99 to Index ranges -24<=h<=24, -31<=k<=31, -34<=l<=26 Reflections collected Independent reflections [R(int) = ] Completeness to theta = % Absorption correction Semi-empirical from equivalents Max. and min. transmission 1.00 and 0.61 Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters / 0 / 863 Goodness-of-fit on F Final R indices [I>2sigma(I)] R1 = , wr2 = R indices (all data) R1 = , wr2 = Largest diff. peak and hole and e.å -3 S23
24 Figure S15. Partial COSY NMR spectrum of 1 with 4.0 equiv of CsF in CD 3 OD/CDCl 3 (1:9, v/v). S24
25 Supporting info for modeling: Molecular mechanics calculations were performed using the MMFF94 force field 12 as implemented in PCModel. 13 Non-default van der Waals parameters used for the cesium cation are described elsewhere. 3 Optimized Cartesian coordinates for the four CsF binding modes are provided below. CsF_crown/pyrrole mode 174 Cs O O O O N C O C C C C C C C C C C C C C O C C C C C C C C C C C C C C O C C S25
26 C C C C C C N C C C C N C C C C N C C C C C C C C C C C C C C C C C C C C C C C C C C O O C C C C C C C C F H S26
27 H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H S27
28 H H H H H H H H H H H H H H H H H H H H H H H H H CsF glycol/pyrrole mode 174 Cs O O O O N C O C C C C C C C C C C C C C O C C C C C S28
29 C C C C C C C C C O C C C C C C C C N C C C C N C C C C N C C C C C C C C C C C C C C C C C C C C C C C C C C S29
30 O O C C C C C C C C F H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H S30
31 H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H CsF crown/crown mode 174 Cs O O O O N C O C C C C C C S31
32 C C C C C C C O C C C C C C C C C C C C C C O C C C C C C C C N C C C C N C C C C N C C C C C C C C C C C C C S32
33 C C C C C C C C C C C C C O O C C C C C C C C F H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H S33
34 H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H CsF pyrrole/pyrrole mode 174 Cs O S34
35 O O O N C O C C C C C C C C C C C C C O C C C C C C C C C C C C C C O C C C C C C C C N C C C C N C C C C N C S35
36 C C C C C C C C C C C C C C C C C C C C C C C C C O O C C C C C C C C F H H H H H H H H H H H H H H H H H H H S36
37 H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H S37
38 H H H H H H H S38
39 References 1. Kim, S. K.; Vargas-Zúñiga, G. I.; Hay, B. P.; Young, N. J.; Delmau, H.; Lee, C.-H.; Kim, J. S.; Lynch, V. M.; Moyer, B. A.; Sessler, J. L. J. Am. Chem. Soc. 2012, 134, Sessler, J. L.; Kim, S. K.; Gross, D. E.; Lee, C.-H; Kim, J. S.; Lynch, V. M. J. Am. Chem. Soc. 2008, 130, Kim, S. K.; Sessler, J. L.; Gross, D. E.; Lee, C.-H.; Kim, J. S.; Lynch, V. M.; Delmau, L. H.; Hay, B. P. J. Am. Chem. Soc. 2010, 132, Custelcean, R.; Delmau, L. H.; Moyer, B. A.; Sessler, J. L.; Cho, W. -S.; Gross, D.; Bates, G. W.; Brooks, S. J.; Light, M. E.; Gale, P. A. Angew. Chem. Int. Ed. 2005, 44, DENZO-SMN. (1997). Z. Otwinowski and W. Minor, Methods in Enzymology, 276: Macromolecular Crystallography, part A, , C. W. Carter, Jr. and R. M. Sweets, Editors, Academic Press. 6. Altomare, A.; Burla, M.C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Cryst. 1999, 32, Sheldrick, G. M. (1994). SHELXL97. Program for the Refinement of Crystal Structures. University of Gottingen, Germany. 8. Rw(F 2 ) = {Σw( F o 2 - F c 2 ) 2 /Σw( F o ) 4 } 1/2 where w is the weight given each reflection. R(F) = Σ( F o - F c )/Σ F o } for reflections with F o > 4(σ(F o )). S = [Σw( F o 2 - F c 2 ) 2 /(n - p)] 1/2, where n is the number of reflections and p is the number of refined parameters. 9. International Tables for X-ray Crystallography (1992). Vol. C, Tables and , A. J. C. Wilson, editor, Boston: Kluwer Academic Press. 10. Sheldrick, G. M. (1994). SHELXTL/PC (Version 5.03). Siemens Analytical X-ray Instruments, Inc., Madison, Wisconsin, USA. 11. CrystalClear 1.40 (2008). Rigaku Americas Corportion, The Woodlands, TX. 12. Halgren, T. A. J. Comp. Chem. 1996, 17, PC Model, v9.0, Serena Software, Serena Software, Box 3076, Bloomington, IN S39
40 Figure S16. 1 H NMR spectrum of 7 recorded in CDCl 3. S40
41 Figure S C NMR spectrum of 7 recorded in CDCl 3. S41
42 Figure S18. 1 H NMR spectrum of 5 recorded in CDCl 3. S42
43 Figure S C NMR spectrum of 5 recorded in CDCl 3. S43
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