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1 Supporting Information Selective EPR detection of primary amines in water with a calix[6]azacryptand-based copper(ii) funnel complex Alex Inthasot,,, Nicolas Le Poul, # Michel Luhmer, Benoit Colasson,,* Ivan Jabin,,* Olivia Reinaud, * Laboratoire de Chimie Organique, Université Libre de Bruxelles (U.L.B.), Avenue F.D. Roosevelt 50, CP160/06, B-1050 Brussels, Belgium. Laboratoire de Résonance Magnétique Nucléaire Haute Résolution, Université Libre de Bruxelles (U.L.B.), Avenue F.D. Roosevelt 50, CP160/08, B-1050 Brussels, Belgium. Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques (CNRS UMR 8601), Université Paris Descartes Sorbonne Paris Cité, 45 rue des Saints-Pères, Paris, France. # Laboratoire de Chimie, Electrochimie Moléculaires et Chimie Analytique (CNRS UMR 6521), Université de Brest, 6 avenue Le Gorgeu, Brest Cedex 3, France. Table of Contents Characterization of water-soluble X 6 tren (4)(Cl) 3 S2 Characterization of [Cu.4](Cl) 5 S7 Recognitions studies S9 EPR simulations for various host-guest complexes S14 Determination of the pseudo-pka shift for octylamine S16 S1
2 1. Characterization of water-soluble X6tren (4)(Cl)3 Figure S1.1. Above: Mass spectrum (ESI+, MeOH) of (4)(PF 6 ) 3. m/z = for the dicationic species [(H.4)(PF 6 ) 2 ] 2+ ; m/z = for the monocationic species [(4)(PF 6 ) 2 ] + ; m/z = for the monocationic species [(H.4)(PF 6 ) 3 ] +. In inset: zoom of the signal attributed to the dicationic species. Below: Simulated isotopic profile and simulated peak list for the signal corresponding to the dicationic species. Figure S1.2. IR spectrum of (4)(PF 6 ) 3. S2
3 Figure S1.3. Edited HSQC spectrum (D 2 O + DCl, ph = 1.1, 600 MHz, 358 K) of (4)(Cl) 3. Figure S1.4. dqfcosy spectrum (D 2 O + DCl, ph = 1.1, 600 MHz, 358 K) of (4)(Cl) 3. S3
4 Figure S1.5. HMBC-8Hz spectrum (D 2 O + DCl, ph = 1.1, 600 MHz, 358 K) of (4)(Cl) 3. Figure S C NMR spectrum (D 2 O + DCl, ph = 1.1, 100 MHz, 358 K) of (4)(Cl) 3. S4
5 Figure S1.7. Left: HRMS (ESI+, MeOH) of (4)(Cl) 3. Peak at m/z: (calc ) for [(4)] 3+ and zoom for this signal. Right: Simulated isotopic profile and simulated peak list for the same signal. Figure S1.8. IR spectrum of (4)(Cl) 3. S5
6 Figure S H NMR spectra (D 2 O, 600 MHz, 298 K) of (4)(Cl) 3 at different phs. 1 Figure S H NMR spectra (D 2 O, ph = 7.2, 600 MHz) of (4)(Cl) 3 at different temperatures. 1 ph modification was achieved with addition of DCl/NaOD and was modified in the same order as the spectra order (from below to above). S6
7 2. Characterization of [Cu.4](Cl)5 Figure S2.1. Left: HRMS (ESI+, MeOH) of [Cu.4](Cl) 5. Peak at m/z: (calc ) for [Cu.4] 5+ and zoom for this signal. Right: Simulated isotopic profile and simulated peak list for the same signal. Figure S2.2. EPR spectra (2 mm, 100 K, X band) of [Cu.4] 5+ in H 2 O at different phs. Left: ph = 12.1 (pink), ph = 11.0 (dark blue), ph = 9.9 (orange). Right: ph = 7.4 (red), ph = 5.0 (blue), ph = 3.0 (green). S7
8 Figure S2.3. IR spectrum of [Cu.4](Cl) 5. Figure S2.4. Left: CVs at a glassy carbon electrode of complex [Cu.4] 5+ (0.3 mm) in 12.5 mm phosphate buffer, ph = 7.4 for 0.02 V/s < v < 0.5 V/s. Right: CV (v = 0.1 V/s) of [Cu(tren)(H 2 O)] 2+ in 12.5 mm phosphate buffer, ph = 7.4. S8
9 3. Recognition studies Figure S3.1. EPR spectra (6 mm of starting complex, 100 K, X band) of [Cu.4] 5+ in phosphate buffer ph = 7.4 (red), and after successive addition of 30 eq. of NaCl, 30 eq. of NaF and 25 eq. of NaN 3 (blue). Figure S3.2. EPR spectra (40 mm of starting complex, 100 K, X band) of [Cu.4] 5+ in phosphate buffer ph = 7.4 (red), with 10 eq. of acetonitrile (blue), 40 eq. of acetonitrile (green) and 100 eq. of acetonitrile (orange). S9
10 Figure S3.3. EPR spectra (40 mm of starting complex, 100 K, X band) of [Cu.4] 5+ in phosphate buffer ph = 7.4 (red), with 40 eq. of ethanol (blue) and 100 eq. of ethanol (green). Figure S3.4. Left: EPR spectra (20 mm of starting complex, 100 K, X band) of [Cu.4] 5+ in phosphate buffer ph = 7.4 (red) and with 10 eq. of octanol (blue). Right: EPR spectra (20 mm of starting complex, 100 K, X band) of [Cu.4] 5+ in phosphate buffer ph = 7.4 (red) and with 10 eq. of PhCN (blue). S10
11 Figure S3.5. Left: EPR spectra (6 mm of starting complex, 100 K, X band) of [Cu.4] 5+ in phosphate buffer ph = 7.4 (red) and with 10 eq. of propylamine (blue). Right: UV-vis spectra (1.4 mm) of [Cu.4] 5+ in phosphate buffer ph = 7.4 (red) and with 12 eq. of propylamine (blue). Figure S3.6. EPR spectra (6 mm of starting complex, X band, 100 K) of [Cu.4] 5+ in phosphate buffer ph = 7.4 (red), and after successive addition of 15 eq. of N- methylbutylamine (blue) and 20 eq. of tert-butylamine (green). S11
12 Figure S3.7. EPR spectra (9 mm of starting complex, 100 K, X band) of [Cu.4] 5+ in phosphate buffer ph = 7.4 (red) and with 1 eq. of tryptamine.hcl (blue). Figure S3.8. EPR spectra (6 mm of starting complex, 100 K, X band) of [Cu.4] 5+ in phosphate buffer ph = 7.4 (red) and with 1 eq. of tyramine (blue). S12
13 Figure S3.9. EPR spectra (2 mm, 100 K, X band) of [Cu.4(octylamine)] 5+ in H 2 O with 10 eq. of the guest at different phs. Left: ph = 12.2 (red), ph = 7.4 (blue), ph = 4.9 (green), ph = 3.1 (orange). Right: ph = 3.1 (orange), ph = 1.9 (black), ph = 1.0 (pink), ph = 5.1 (brown). 2 Figure S3.10. EPR spectra (20 mm of starting complex, 100 K, X band) of [Cu.4] 5+ in phosphate buffer ph = 7.4 (red), and after successive addition of 20 eq. of octanol (blue) and 10 eq. of heptylamine (green). 2 ph is progressively decreased with HCl to ph = 1.0 in the sequence presented, then put at ph = 5.1 with NaOH. S13
14 Figure S3.11. EPR spectra (20 mm of starting complex, 100 K, X band) of [Cu.4] 5+ in phosphate buffer ph = 7.4 (red), and after successive addition of 20 eq. of PhCN (blue), 40 eq. of benzylic alcohol (green) and 20 eq. of benzylamine (orange). 4. EPR simulation for various host-guest complexes Figure S4.1. Experimental (solid lines, red) and simulated (dashed lines, blue) EPR spectra of [Cu.4] 5+ (phosphate buffer, ph = 7.4, 100 K, X band) S14
15 Figure S4.2. Experimental (solid lines, red) and simulated (dashed lines, blue) EPR spectra of [Cu.4] 5+ (phosphate buffer, ph = 7.4, 100 K, X band) with 10 eq. of various amino-guests. Trace a, guest is propylamine. Trace b, guest is octylamine. Trace c, guest is tryptamine. Table S1. Comparison of the EPR parameters of the calix[6]tren-based Cu II complexes obtained in water ([Cu.4] 5+, phosphate buffer, ph = 7.4) and in dichloromethane a with various guest ligands. Solvent Guest EPR parameters (X band, 100 K) (A/10-4 cm -1 ) Water H 2 O g // = 2.24 (160.0), g = 2.06 Water Propylamine g 1 = (64.3), g 2 = (81.5), g 3 = (124.4) Water Octylamine g 1 = (64.0), g 2 = (49.0), g 3 = (120.0) Water Tryptamine g 1 = (59.2), g 2 = (31.7), g 3 = (123.4) CH 2 Cl 2 H 2 O g 1 = (36.4), g 2 = (69.7), g 3 = (145.4) CH 2 Cl 2 EtOH g 1 = (58.2), g 2 = (37.1), g 3 = (148.5) CH 2 Cl 2 MeCN g 1 = (52.4), g 2 = (59.5), g 3 = (141.4) a Izzet, G.; Douziech, B.; Prangé, T.; Tomas, A.; Jabin, I.; Le Mest, Y.; Reinaud, O. Calix[6]tren and copper(ii): A Third Generation of Funnel Complexes on the Way to Redox Calix-zymes. Proc. Nat. Acad. Sci. 2005, 102, S15
16 5. Determination of the pseudo-pka for octylamine The formation constant K and K' ph are defined according to the following equilibrium: From the analysis of the octylamine titration, K' 7.4 value was found to be ca M -1 leading to K ~ 4.0x10-4. We can estimate a pseudo-pka (-logk) of ~ Compared to the pk a of free octylamine of ca. 10.6, a pk a shift of ca. 7.2 is observed in the presence of the receptor. 3 It is calculated considering that the inclusion complex is formed at 90 % when only one species can be detected on the EPR spectrum. S16
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