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1 This journal is The Royal Society of Chemistry 212 Supplementary Information Host Guest Chemistry of Linked -Cyclodextrin Trimers and Adamantyl Substituted Poly(acrylate)s in Aqueous Solution Hanh-Trang Nguyen, a Duc-Truc Pham, a Stephen F. Lincoln,* a Jie Wang, b Xuhong Guo, b Christopher J. Easton c and Robert K. Prud homme d a School of Chemistry and Physics, University of Adelaide, Adelaide, SA 55, Australia stephen.lincoln@adelaide.edu.au b State Key Laboratory of Chemical Engineering, East China University of Science and Technology, Shanghai 2237, China c Research School of Chemistry, Australian National University, Canberra, ACT 2, Australia d Department of Chemical Engineering, Princeton University, Princeton, NJ 8544 (USA) 1
2 This journal is The Royal Society of Chemistry 212 Mass spectra Relative intensity m/z Fig. S1. Mass spectrum of β-cd 3 bz, positive ion mode, singly charged species [M+H] +, [M+Na] + and [M+K] Relative intensity m/z Fig. S2. Mass spectrum of β-cd 3 bz, negative ion mode, doubly charged species [M-2H] Relative intensity m/z Fig. S3. Mass spectrum of β-cden 3 bz, positive ion mode, singly charged species [M+H] +, [M+Na] + and [M+K] +. 2
3 This journal is The Royal Society of Chemistry Relative intensity m/z Fig. S4. Mass spectrum of β-cden 3 bz, negative ion mode, singly charged specie [M-H] -. 1 H and 13 C NMR Spectra Fig. S5. 1 H NMR spectrum of 1,3,5 trinitrophenyl benzene in d 6 -dimethylsufoxide. Fig. S6. 1 H NMR spectrum of β-cd 3 bz in D 2 O. Fig. S7. 13 C NMR spectrum of β-cd 3 bz in D 2 O. 3
4 This journal is The Royal Society of Chemistry 212 Fig. S8. 1 H NMR spectrum of β-cden 3 bz in D 2 O. Fig. S9. 13 C NMR spectrum of β-cden 3 bz in D 2 O. 2D NOESY 1 H NMR Spectra Ar H -CD H1 HOD -CD H2-6 AD H2-4 -CD H2-6 PAA, AD H Fig. S1. 2D NOESY 1 H NMR (6 MHz) spectrum (mixing time 3ms) of a solution 1. x 1-3 mol dm -3 in β-cd 3 bz and 1. wt. % in 3% substituted PAAAD such that the adamantyl substituent concentration is 3. x 1-3 mol dm -3 in D 2 O (pd 7. phosphate buffer, I =.1 mol dm -3 ) at 298.2K. The rectangle encloses the crosspeaks arising from interaction between the annular β-cd H3,5,6 protons of β-cd 3 bz and the adamantyl substituent H1-4 protons of PAAAD. 4
5 PAA, AD H en N-CH2 Ar H AD H2-4 HOD -CD H1 Electronic Supplementary Material (ESI) for Polymer Chemistry This journal is The Royal Society of Chemistry 212 PAA, AD H hn -CH2 -CD H1 Ar H hn N-CH2 AD H2-4 HOD Fig. S11. 2D NOESY 1H NMR (6 MHz) spectrum (mixing time 3ms) of a solution 1. x 1-3 mol dm-3 in β-cd3bz and 1. wt. % in 3% substituted PAAADen such that the adamantyl substituent concentration is 3. x 1-3 mol dm-3 in D2O (pd 7. phosphate buffer, I =.1 mol dm-3) at 298.2K. The rectangle encloses the crosspeaks arising from interaction between the annular β-cd H3,5,6 protons of β-cd3bz and the adamantyl substituent H1-4 protons of PAAADen. A B Fig. S12. 2D NOESY 1H NMR (6 MHz) spectrum (mixing time 3ms) of a solution 1. x 1-3 mol dm-3 in β-cd3bz and 1. wt. % in 3% substituted PAAADhn such that the adamantyl substituent concentration is 3. x 1-3 mol dm-3 in D2O (pd 7. phosphate buffer, I =.1 mol dm-3) at 298.2K. Rectangles A and B enclose the cross-peaks arising from interaction between the annular β-cd H3,5,6 protons of βcd3bz and the adamantyl substituent H1-4 protons and the tether hexyl 2-5 methylene protons of PAAADhn, respectively. 5
6 -CD H1 PAA, AD H A ddn -CH2 Ar H ddn N-CH2 AD H2-4 HOD Electronic Supplementary Material (ESI) for Polymer Chemistry This journal is The Royal Society of Chemistry 212 B PAA, AD H -CD H1HOD Ar H en N-CH2 AD H2-4 Fig. S13. 2D NOESY 1H NMR (6 MHz) spectrum (mixing time 3ms) of a solution 1. x 1-3 mol dm-3 in β-cd3bz and 1. wt. % in 3% substituted PAAADddn such that the adamantyl substituent concentration is 3. x 1-3 mol dm-3 in D2O (pd 7. phosphate buffer, I =.1 mol dm-3) at 298.2K. Rectangles A and B enclose the cross-peaks arising from interaction between the annular β-cd H3,5,6 protons of βcd3bz and the adamantyl substituent H1-4 protons and the tether dodecyl 2-11 methylene protons of PAAADddn, respectively. Fig. S14. 2D NOESY 1H NMR (6 MHz) spectrum (mixing time 3ms) of a solution 1. x 1-3 mol dm-3 in β-cden3bz and 1. wt. % in 3% substituted PAAAD such that the adamantyl substituent concentration is 3. x 1-3 mol dm-3 in D2O (pd 7. phosphate buffer, I =.1 mol dm-3) at 298.2K. The rectangle encloses the crosspeaks arising from interaction between the annular β-cd H3,5,6 protons of βcden3bz and the adamantyl substituent H1-4 protons of PAAAD. 6
7 -CD H1 en N-CH2 AD H2-4 HOD Ar H PAA, AD H Electronic Supplementary Material (ESI) for Polymer Chemistry This journal is The Royal Society of Chemistry 212 -CD H1 A ddn -CH2 PAA, AD H AD H2-4 Ar H HOD ddn N-CH2 Fig. S15. 2D NOESY 1H NMR (6 MHz) spectrum (mixing time 3ms) of a solution 1. x 1-3 mol dm-3 in β-cden3bz and 1. wt. % in 3% substituted PAAADen such that the adamantyl substituent concentration is 3. x 1-3 mol dm-3 in D2O (pd 7. phosphate buffer, I =.1 mol dm-3) at 298.2K. The rectangle encloses the crosspeaks arising from interaction between the annular β-cd H3,5,6 protons of βcden3bz and the adamantyl substituent H1-4 protons of PAAADen. B Fig. S16. 2D NOESY 1H NMR (6 MHz) spectrum (mixing time 3ms) of a solution 1. x 1-3 mol dm-3 in β-cden3bz and 1. wt. % in 3% substituted PAAADddn such that the adamantyl substituent concentration is 3. x 1-3 mol dm-3 in D2O (pd 7. phosphate buffer, I =.1 mol dm-3) at 298.2K. Rectangles A and B enclose the cross-peaks arising from interaction between the annular β-cd H3,5,6 protons of β-cden3bz and the adamantyl substituent H1-4 protons and the tether dodecyl 2-11 methylene protons of PAAADddn, respectively. 7
8 This journal is The Royal Society of Chemistry 212 ITC Data µj/s -1-1 kj/mol -CD [ -CD]/[adamantyl substituent] Fig. S17. Isothermal titration calorimetry (ITC) data for.13 wt. % PAAAD ([adamantyl substituent] = mol dm -3 ) with β-cd ( mol dm -3 ) in aqueous phosphate buffer at ph 7. (I =.1 mol dm -3 ) at K. The top section shows the raw ITC experimental plot. The bottom section shows a solid curve representing the best fit to the data points of an algorithm for an equilibrium analogous to that shown in eqn. 1 in the published text for the complexation by β-cd of the adamantyl substituent guests of PAAAD. 8
9 This journal is The Royal Society of Chemistry µj/s kj/mol -CD [ -CD]/[adamantyl substituent] Fig. S18. Isothermal titration calorimetry (ITC) data for.37 wt. % PAAADhn ([adamantyl substituent] = mol dm -3 ) with β-cd ( mol dm -3 ) in aqueous phosphate buffer at ph 7. (I =.1 mol dm -3 ) at K. The top section shows the raw ITC experimental plot. The bottom section shows a solid curve representing the best fit of an algorithm. The bottom section shows a solid curve representing the best fit to the data points of an algorithm for an equilibrium analogous to that shown in eqn. 1 in the published text for the complexation by β-cd of the adamantyl substituent guests of PAAADhn. 9
10 This journal is The Royal Society of Chemistry µj/s kj/mol -CD [ -CD]/[adamantyl substituent] Fig. S19. Isothermal titration calorimetry (ITC) data for.21 wt. % PAAADddn ([adamantyl substituent] = mol dm -3 ) with β-cd ( mol dm -3 ) in aqueous phosphate buffer at ph 7. (I =.1 mol dm -3 ) at K. The top section shows the raw ITC experimental plot. The bottom section shows a solid curve representing the best fit to the data points of an algorithm for an equilibrium analogous to that shown in eqn. 1 in the published text for the complexation by β-cd of the adamantyl substituent guests of PAAADddn. 1
11 This journal is The Royal Society of Chemistry µj/s -1-5 kj/mol -CD 3 bz [ -CD 3 bz]/[adamantyl substituent] Fig. S2. Isothermal titration calorimetry (ITC) data for.13 wt. % PAAAD ([adamantyl substituent] = mol dm -3 ) with β-cd 3 bz ( mol dm -3 ) in aqueous phosphate buffer at ph 7. (I =.1 mol dm -3 ) at K. The top section shows the raw ITC experimental plot. The bottom section shows a solid curve representing the best fit to the data points of an algorithm for an equilibrium analogous to that shown in eqn. 2 in the published text for the complexation by β- CD 3 bz of the adamantyl substituent guests of PAAAD.. 11
12 This journal is The Royal Society of Chemistry µj/s kj/mol -CD 3 bz [ -CD 3 bz]/[adamantyl substituent] Fig. S21. Isothermal titration calorimetry (ITC) data for.2 wt. % PAAADen ([adamantyl substituent] = mol dm -3 ) with β-cd 3 bz ( mol dm -3 ) in aqueous phosphate buffer at ph 7. (I =.1 mol dm -3 ) at K. The top section shows the raw ITC experimental plot. The bottom section shows a solid curve representing the best fit to the data points of an algorithm for an equilibrium analogous to that shown in eqn. 2 in the published text for the complexation by β- CD 3 bz of the adamantyl substituent guests of PAAADen. 12
13 This journal is The Royal Society of Chemistry µj/s kj/mol -CD 3 bz [ -CD 3 bz]/[adamantyl substituent] Fig. S22. Isothermal titration calorimetry (ITC) data for.21 wt. % PAAADddn ([adamantyl substituent] = mol dm -3 ) with β-cd 3 bz ( mol dm -3 ) in aqueous phosphate buffer at ph 7. (I =.1 mol dm -3 ) at K. The top section shows the raw ITC experimental plot. The bottom section shows a solid curve representing the best fit to the data points of an algorithm for an equilibrium analogous to that shown in eqn. 2 in the published text for the complexation by β- CD 3 bz of the adamantyl substituent guests of PAAADddn. 13
14 This journal is The Royal Society of Chemistry (a) (b) µj/s kj/mol -CDen 3 bz [ -CDen 3 bz]/[adamantyl substituent] Fig. S23. Isothermal titration calorimetry (ITC) data for.13 wt. % PAAAD ([adamantyl substituent] = mol dm -3 ) with β-cden 3 bz ( mol dm -3 ) in aqueous phosphate buffer at ph 7. (I =.1 mol dm -3 ) at K. The top section shows the raw ITC experimental plot where (a) is the data for dilution of β- CDen 3 bz and (b) is that for the titration obtained as described in the published text. The bottom section shows a solid curve representing the best fit to the corrected titration data points of an algorithm for an equilibrium analogous to that shown in eqn. 3 in the published text for the complexation by β-cden 3 bz of the adamantyl substituent guests of PAAADddn. 14
15 This journal is The Royal Society of Chemistry (a) (b) -1-2 µj/s -3-4 kj/mol -CDen 3 bz [ -CDen 3 bz]/[adamantyl substituent] Fig. S24. Isothermal titration calorimetry (ITC) data for.2 wt.% PAAADen ([adamantyl substituent] = mol dm -3 ) with β-cden 3 bz ( mol dm -3 ) in aqueous phosphate buffer at ph 7. (I =.1 mol dm -3 ) at K. The top section shows the raw ITC experimental plot where (a) is the data for dilution of β- CDen 3 bz and (b) is that for the titration obtained as described in the published text. The bottom section shows a solid curve representing the best fit to the corrected titration data points of an algorithm for an equilibrium analogous to that shown in eqn. 3 in the published text for the complexation by β-cden 3 bz of the adamantyl substituent guests of PAAADen. 15
16 This journal is The Royal Society of Chemistry (a) (b) -1 µj/sec -2-3 kj/mole -CDen 3 bz [ -CDen 3 bz]/[adamantyl substituent] Fig. S25. Isothermal titration calorimetry (ITC) data for.2 wt. % PAAADhn ([adamantyl substituent] = mol dm -3 ) with β-cden 3 bz ( mol dm -3 ) in aqueous phosphate buffer at ph 7. (I =.1 mol dm -3 ) at K. The top section shows the raw ITC experimental plot where (a) is the data for dilution of β- CDen 3 bz and (b) is that for the titration obtained as described in the published text. The bottom section shows a solid curve representing the best fit to the corrected titration data points of an algorithm for an equilibrium analogous to that shown in eqn. 3 in the published text for the complexation by β-cden 3 bz of the adamantyl substituent guests of PAAADhn. 16
17 This journal is The Royal Society of Chemistry (a) (b) -1 µj/s kj/mol -CDen 3 bz [ -CDen 3 bz]/[adamantyl substituent] Fig. S26. Isothermal titration calorimetry (ITC) data for.21 wt. % PAAADddn ([adamantyl substituent] = mol dm -3 ) with β-cden 3 bz ( mol dm -3 ) in aqueous phosphate buffer at ph 7. (I =.1 mol dm -3 ) at K. The top section shows the raw ITC experimental plot where (a) is the data for dilution of β- CDen 3 bz and (b) is that for the titration obtained as described in the published text. The bottom section shows a solid curve representing the best fit to the corrected titration data points of an algorithm for an equilibrium analogous to that shown in eqn. 3 in the published text for the complexation by β-cden 3 bz of the adamantyl substituent guests of PAAADddn. 17
18 This journal is The Royal Society of Chemistry 212 Table S1. Variation of the chemical shift of the aromatic 1 H resonance of -CDen 3 bz with concentration. a,b [ -CDen 3 bz] mol dm -3 ppm b a In D 2 O phosphate buffer at pd 7., I =.1 mol dm -3 and K. b Chemical shift downfield of HOD resonance at 4.79 ppm which is downfield of the methyl resonance of sodium-3(trimethylsilyl)propanesulfonate at. ppm (H. E. Gottlieb, V. Kotlyar and A Nudelman, J. Org. Chem., 1997, 62, ) Determined at 3 MHz. 18
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