Mechanically Induced Pyrogallol[4]arene Hexamer Assembly in the Solid State Extends the Scope of Molecular Encapsulation
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1 Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2017 Electronic Supplementary Information for: Mechanically Induced Pyrogallol[4]arene Hexamer Assembly in the Solid State Extends the Scope of Molecular Encapsulation Sara N. Journey, Kristine L. Teppang, Cesar A. Garcia, Shaylyn A. Brim, David Onofrei, J. Bennett Addison, Gregory P. Holland, and Byron W. Purse* Department of Chemistry and Biochemistry, San Diego State University, 5500 Campanile Dr. San Diego CA 92182, United States. * Table of Contents 1. NMR Spectrum of Decyl Pyrogallol[4]arene 1a S3 2. NMR Spectra of Propyl Pyrogallol[4]arene1b S4 3. Molar Equivalences of Host to Guest Stoichiometric Ratios S5 4. GHSQC Spectrum of Encapsulated Fluorene Complex S H PFG-DOSY NMR Plots of Free and Encapsulated Fluorene Using Ball-Mill and Melting Method 6. Stacked Plot of Encapsulated Pyrene (Melted and Ball-Milled) S10 7. Solution 1 H NMR Studies of Milled Stoichiometric Mixtures of Pyrogallol[4]arene 1a and Guest as a Function of Milling Time 8. Kinetic Studies Description S14 9. Percent Encapsulation Graphs, Data Integration Tables, and Peak Identification Plots S7-S9 10. First Order Kinetics Equations for the Time-dependent [2.2] paracyclophane Solvent Guest Exchange From 1a6 in CDCl3 Solution. S Time Dependent [2.2]paracyclophane Solvent Guest Exchange From 1a6 in CDCl Stacked 1 H NMR Spectrum of Time Dependent [2.2]paracyclophane Solvent Guest Exchange From 1a6 in CDCl3 Solution. 13. Encapsulation of Both 1-adamantanecarboxylic acid and 1,5-diaminonaphthalene S11-S14 S15-S28 S29-S30 S31 S32 S1
2 14. 1 H NMR Spectra of Ball-milled Fluorene (t=0) that was Aged in a Vial Without Further Agitation H NMR Spectra of Same Ball-milled Sample of Encapsulated Fluorene in a) CCl4 with a D-benzene Solvent Lock and b) CDCl3 S33 S34 S2
3 NMR Spectrum for Decyl Pyrogallol[4]arene 1a Figure S1. 1 H NMR Spectrum for decyl pyrogallol[4]arene 1a (1mM, 400MHz, CDCl3, 298K). Figure S2. 13 C NMR Spectrum for decyl pyrogallol[4]arene 1a (1mM, 100MHz, CDCl3, 298K). S3
4 NMR Spectra for Propyl Pyrogallol[4]arene 1b Figure S3. 1 H NMR Spectrum for propyl pyrogallol[4]arene1b (1mM, 400MHz, CDCl3, 296K). Figure S4. 13 C NMR Spectrum for propyl pyrogallol[4]arene1b (3mM, 100MHz, DMSO-d6, 296K). S4
5 Host-Guest Stoichiometry Table S1. Maximum Number of Guest Molecules Encapsulated in Each Pyrogallol[4]arene Hexamer 1a6 or 1b6 a Entry Guest 1 1-adamantanecarboxcylic acid Guest VdW Volume / Å 3 Max Number Encapsulated anthracene ,5-diaminonaphthalene fluoranthene fluorene [2.2]paracyclophane Packing Coefficient b a Maximum guest occupancy was determined by molecular modeling and based on our past publications on pyrogallol[4]arene hexamers. 1 b Packing coefficient is the ratio of the total VdW volume of the guests to the 1300 Å 3 volume of the capsule s cavity. GHSQC Spectrum of Encapsulated Fluorene Complex Figure S5. GHSQC Spectrum for fluorene encapsulated in the 1a6 hexamer (3mM, 500Hz, CDCl3, 298K). 1 Chapin, J.C.; Kvasnica, M.; Purse, B.W. Molecular Encapsulation in Pyrogallolarene Hexamers Under Nonequilibrium Conditions. J. Am. Chem. Soc. 2012, 134, S5
6 Figure S6. Annotated GHSQC of fluorene4 1a6 encapsulation complex (1mM, 500MHz, CDCl3, 298K). 1 H PFG-DOSY NMR Plots of Free and Encapsulated Fluorene 1 H PFG-DOSY NMR data was collected at 25 C on a 600 MHz Bruker Avance IIIHD NMR spectrometer equipped with a HCN TXI room temperature probe with standard gradient coils capable of 50 Gauss/cm gradient pulses. Three separate samples were prepared: A) 4:6 mixture of fluorene / pyrogallol[4]arene dissolved in CDCl3, B) encapsulated fluorene in pyrogallol[4]arene prepared using the melting method, and C) encapsulated fluorene in pyrogallol[4]arene prepared using the ball-mill method. All samples were prepared using the same total mass concentration at 10 mg/ml. To restrict sample convection, a common problem in DOSY NMR experiments using low viscosity solvents, 0.4 ID glass capillary tubes were dropped into standard 5 mm NMR tubes. 2 Acquisition parameters for 1 H DOSY NMR were: ledbpgp2s Bruker pulse program, 8 scans and 32 DOSY points, 16 ppm spectral width, 1.7 second acquisition time and a 4 second recycle delay. The diffusion delays big-delta and littledelta were set to 40 ms and 3 ms, respectively. Data were processed using DosyToolbox version 2.5. Each individual FID was phased and baseline corrected, and the decaying peak heights were fit by DosyToolbox. Probe gradient strengths were calibrated using a standard doped 1% H2O in D2O sample by setting the diffusion coefficient of water to x m 2 /s. 2 T. Iwashita, T. Konuma, E. Harada, S. Mori, and K. Sugase, Use of glass capillaries to suppress thermal convection in NMR tubes in diffusion measurements, Magnetic Resonance in Chemistry, vol. 54, no. 9, pp , Sep S6
7 Figure S7. 1 H PFG-DOSY NMR plots showing non-encapsulated fluorene and pyrogallol[4]arene 1a free in solution. S7
8 Figure S8. 1 H PFG-DOSY NMR plots showing the 4 fluorene : 6 pyrogallol[4]arene 1a encapsulated complex prepared using melting and cooling prior to dissolution in CDCl 3. S8
9 Figure S9. 1 H PFG-DOSY NMR plots showing 4 fluorene : 6 pyrogallol[4]arene 1a prepared using the ball-milling method. S9
10 Stacked Plot of Encapsulated Pyrene (Melting Cooling and Ball-Milled) a b Figure S10. Stacked plot of pyrene3 1a6 encapsulation complex formed from a.) ball-milling method, and b.) melting method 1 (1mM, 400MHz, CDCl3, 298K). 1 Chapin, J.C.; Kvasnica, M.; Purse, B.W. Molecular Encapsulation in Pyrogallolarene Hexamers Under Nonequilibrium Conditions. J. Am. Chem. Soc. 2012, 134, S10
11 Solution 1 H NMR Spectra of Milled Stoichiometric Mixtures of Pyrogallol[4]arene 1a and Guest as a Function of Milling Time. Figure S11. Stacked plot of solution 1 H NMR spectra of milled mixtures of 3 fluoranthene : 6 decyl pyrogallol[4]arene 1a as a function of time (min). (1mM, 500MHz, CDCl3,293K). Figure S12. Stacked plot of solution 1 H NMR spectra of milled mixtures of 4 fluorene : 6 decyl pyrogallol[4]arene 1a as a function of time (min). (1mM, 500MHz, CDCl3, 293K) S11
12 Figure S13. Stacked plot of solution 1 H NMR spectra of milled mixtures of 3 pyrene : 6 decyl pyrogallol[4]arene 1a as a function of time (min). (1mM, 500MHz, CDCl3, 293K). Figure S14. Stacked plot of solution 1 H NMR spectra of milled mixtures of 3 anthracene : 6 decyl pyrogallol[4]arene 1a as a function of time (min). (1mM, 500MHz, CDCl3, 293K) S12
13 Figure S15. Stacked plot of solution 1 H NMR spectra of milled mixtures of 3 1- adamantanecarboxylic acid : 6 decyl pyrogallol[4]arene 1a as a function of time (min). (1mM, 500MHz, CDCl3, 293K). Figure S16. Stacked plot of solution 1 H NMR spectra of milled mixtures of 4 1,5- diaminonaphthalene : 6 decyl pyrogallol[4]arene 1a as a function of time (min). (1mM,500MHz, CDCl3, 293K). S13
14 Figure S17. Stacked plot of solution 1 H NMR spectra of milled mixtures of 3 [2.2] paracyclophane : 6 decyl pyrogallol[4]arene 1a as a function of time (min). (1mM, 500MHz, CDCl3, 293K). Kinetic Studies Description We used the integration of solution 1 H NMR spectra of samples to track the formation of guest encapsulation complexes in pyrogallol[4]arene hexamer 1a6 as a function of the duration of milling. Percent encapsulation was determined by normalizing the NMR spectra to the methine signal of 1a at 4.4 ppm and tracking the appearance of signals for encapsulated guests. The data do not clearly fit standard solution kinetic models such as first and second order rate laws. We analyzed the data by plotting the % encapsulation of guest as a function of milling duration and using the relatively linear slope for the first few time points to calculate an average initial rate. While the data are more variable than is typical of standard solution kinetics a fact that is not surprising given the imperfect homogeneity of the milled materials we were able to resolve clear kinetics differences in the rate of encapsulation of the respective guests. All 1 H NMR samples were obtained using a Varian 500MHz NMR at 293K. The time dependent guest release of [2.2]paracyclophane (i.e. as encapsulated [2.2]paracyclophane is release from the capsule, it is replaced with encapsulated solvent molecules) in 1a6 follows a clear first order kinetic model. The 1 H NMR signals for encapsulated guest were integrated and normalized to the 1a6 methine to determine the percent encapsulation as a function of time in CDCl3 solution. The data were fitted to a non-linear curve fitting model for first-order kinetics in Origin 8.1 to determine the rate of guest release over time. All samples were obtained using a Varian 400MHz NMR at 293K. S14
15 Percent Encapsulation Graphs Table S2. Integrated 1 H NMR signals for kinetics and percent encapsulation calculations for solution 1 H NMR spectra of milled mixtures of 3 fluoranthene : 6 decyl pyrogallol[4]arene 1a as a function of time (min). D Figure S18. Peaks A-F were normalized to peak G (24 H, 1a6 methine), then used for the calculation of percent encapsulation and kinetics (1mM, 500MHz, CDCl3, 296K). S15
16 80 Percent Encapsulation Trial 1 Trial 2 Trial Time (minutes) Figure S19. Percent encapsulation plot for three trials of milled mixtures of 3 fluoranthene : 6 decyl pyrogallol[4]arene 1a as a function of time (min). S16
17 Table S3. Integrated 1 H NMR signals for kinetics and percent encapsulation calculations for solution 1 H NMR spectra of milled mixtures of 4 fluorene : 6 decyl pyrogallol[4]arene 1a as a function of time (min). Figure S20. Peaks A-D were normalized to peak E (24 H, 1a6 methine), then used for the calculation of percent encapsulation and kinetics. (1mM, 500MHz, CDCl3, 296K). S17
18 Percent Encapsulation Percent Encapsulation Trial 3 Trial 2 Trial Time (minutes) Figure S21. Percent encapsulation plot for three trials of milled mixtures of 4 fluorene : 6 decyl pyrogallol[4]arene 1a as a function of time (min) Trial 1 Trial 2 Trial 3 Trial Time (minutes) Figure S22. Percent encapsulation plot for four trials of milled mixtures of 4 fluorene : 6 decyl pyrogallol[4]arene 1a with extended milling times. S18
19 Percent Encapsulation Trial 1 Trial 2 Trial 3 Trial Time (minutes) Figure S23. Percent encapsulation plot for four trials of milled mixtures of 4 fluorene : 6 decyl pyrogallol[4]arene 1a with extended milling times without disturbing the chambers. For this data set only, we prepared independent experiments for each time point, milling fresh samples continuously and measuring percent encapsulation only once at the end of the experiment. The data clearly show much more scatter than is seen in Figures S19 and S20. Figure S24. Percent encapsulation plot for three trials of milled mixtures of 4 fluorene : 6 propyl pyrogallol[4]arene1b with extended milling times. S19
20 Table S4. Integrated 1 H NMR signals for kinetics and percent encapsulation calculations for solution 1 H NMR spectra of milled mixtures of 3 anthracene : 6 decyl pyrogallol[4]arene 1a as a function of time (min). Figure S25. Peaks A-D were normalized to peak E (24 H, 1a6 methine), then used for the calculation of percent encapsulation and kinetics calculations (1mM, 500MHz, CDCl3, 296K). S20
21 70 Trial 1 Trial 2 Trial 3 60 Percent Encapsulation Time (minutes) Figure S26. Percent encapsulation plot for three trials of milled mixtures of 3 anthracene : 6 decyl pyrogallol[4]arene 1a as a function of time (min). S21
22 Table S5. Integrated 1 H NMR signals for kinetics and percent encapsulation calculations for solution 1 H NMR spectra of milled mixtures of 3 1-adamantanecarboxylic acid anthracene : 6 decyl pyrogallol[4]arene 1a as a function of time (min). Figure S27. Peaks B-F were normalized to peak A (24 H, 1a6 methine), then used for the calculation of percent encapsulation and kinetics(1mm, 500MHz, CDCl3, 296K). S22
23 40 35 Trial 1 Trial 2 Trial Trial Time Figure S28. Percent encapsulation plot for three trials of milled mixtures of 3 1-adamantanecarboxylic acid anthracene : 6 decyl pyrogallol[4]arene 1a as a function of time (min). S23
24 Table S6. Integrated 1 H NMR signals for kinetics and percent encapsulation calculations for solution 1 H NMR spectra of milled mixtures of 4 1,5-diaminonaphthalene : 6 decyl pyrogallol[4]arene 1a as a function of time (min). Figure S29. Peaks A-C were normalized to peak D (24 H, 1a6 methine), then used for the calculation of percent encapsulation and kinetics (1mM, 500MHz, CDCl3, 296K). S24
25 35 Trial 1 Trial 2 Trial Trial Time (minutes) Figure S30. Percent encapsulation plot for three trials of milled mixtures of 4 1,5- diaminonaphthalene : 6 decyl pyrogallol[4]arene 1a as a function of time (min). S25
26 Table S7. Integrated 1 H NMR signals for kinetics and percent encapsulation calculations for solution 1 H NMR spectra of milled mixtures of 3 [2.2]paracyclophane : 6 decyl pyrogallol[4]arene 1a as a function of time (min). Figure S31. Peaks B-D were normalized to peak C (24 H, 1a6 methine), then used for the calculation of percent encapsulation and kinetics (1mM, 400MHz, CDCl3, 296K). S26
27 Percent Encapsulation Trial 1 Trial 2 Trial 3 Percent Encapsulation Time (minutes) Figure S32. Percent encapsulation plot for three trials of milled mixtures of 3 [2.2]paracyclophane : 6 decyl pyrogallol[4]arene 1a as a function of time (min) Trial 1 Trial Time (minutes) Figure S33. Percent encapsulation plot for two trials of milled mixtures of 3 [2.2]paracyclophane : 6 decyl pyrogallol[4]arene 1a with extended milling time. S27
28 Percent Encapsulation Equation y = a + b*x Weight No Weightin Residual Sum of Squares Pearson's r Adj. R-Squa Value Standard Err Trial 1 Intercept Trial 1 Slope Trial 2 Intercept Trial 2 Slope Trial 3 Intercept Trial 3 Slope Trial 1 Trial 2 Trial 3 Linear Fit of Sheet1 Trial 1 Linear Fit of Sheet1 Trial 2 Linear Fit of Sheet1 Trial 3 Time (minutes) Figure S34. Initial rate constant for three trials of ball-milled mixtures of 4 fluorene : 6 decyl pyrogallol[4]arene. First Order Kinetics Equations for the Time-dependent [2.2]paracyclophane Solvent Guest Exchange from 1a6 in CDCl3 Solution. ln[a] = -kt + ln[a]0 (1) A = A0e -kt (2) t1/2 = ln (2) k (3) S28
29 Time Dependent [2.2]paracyclophane Solvent Guest Exchange from 1a6 in CDCl3. Percent ExpDec1 Fit of Sheet1 Percent Percent Encapsulation Value Standard Error y A t Time Figure S35. Plot of the percent encapsulation (in decimal) of [2.2]paracyclophane in 1a6 as a function of time in CDCl3 solution at 295 K. Time is in hours. The data are fit to a first-order kinetic model using nonlinear regression, giving a rate constant for guest release k = h 1 and t½ = 26 h. The percent encapsulation for each time point was determined from the integration of signals for bound guest as normalized to the methine of 1a6. (Figure S37). S29
30 Regular Residual of Percent Encapsulation Independent Variable Figure S36. Origin 8.1. Residual values from the fitted plot of encapsulated [2.2]paracyclophane in CDCl3. S30
31 Stacked 1 H NMR Spectrum of Time Dependent [2.2]paracyclophane Solvent Guest Exchange from 1a6 in CDCl3 Solution. Figure S37. Stacked 1 H NMR spectra of time dependent [2.2]paracyclophane solvent guest exchange, time is in hours (1mM, 400MHz, CDCl3, 296K). S31
32 Encapsulation of Both 1-adamantanecarboxylic acid and 1,5-diaminonaphthalene Figure S38. Stacked 1 H NMR of the result of taking a mixture of 0.2 g 1a plus 0.1 g 1- adamantanecarboxylic acid and 0.1 g 1,5-diaminonaphthalene, and either (a) melting and cooling the mixture using a heat gun, or (b) ball-milling for 50 minutes. (1mM, 500MHz, CDCl3, 296K). S32
33 1 H NMR Spectra of Mixture of 4 fluorene : 6 decyl pyrogallol[4]arene 1a Ball-milled for 2 Minutes and then Left in a Vial, in the Dark, to Age Without Further Agitation. Figure S39. Stacked 1 H NMR spectra of a mixture of 4 fluorene : 6 decyl pyrogallol[4]arene 1a ball-milled for 2 minutes and then left in a vial, in the dark, to age without further agitation. Samples were removed from this vial and the NMR spectrum was recorded after sample dissolution in CDCl3. Time is in minutes with t = 0 set immediately after ball milling for 2 minutes (1mM, 500MHz, CDCl3, 298K). S33
34 1 H NMR Spectra of 4 fluorene : 6 pyrogallol[4]arene 1a ball-milled at 30Hz for 50 minutes then Dissolved and Measured in a) CCl4 with a C6D6 External Solvent Lock and b) CDCl3 Figure S40. 1 H NMR Spectra of 4 fluorene : 6 pyrogallol[4]arene 1a ball-milled at 30Hz for 50 minutes, then dissolved in a.) CCl4 with a C6D6 external solvent lock, and b.) CDCl3 (1mM, 500 MHz, 298K). S34
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