the Recognition of Hydrogenpyrophosphate in
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1 Biscarbazolylureas as Selective Receptors for the Recognition of Hydrogenpyrophosphate in Aqueous Media Guzmán Sánchez, Arturo Espinosa*, David Curiel, Alberto Tárraga and Pedro Molina* SUPPLEMENTARY INFRMATIN 1 H-NMR and 13 C-NMR...2 UV-Vis spectra...5 Titrations in pure acetonitrile...7 Titrations in acetonitrile/water...9 NMR titrations..14 Deprotonation tests...15 NCIplot analyses...17 Calculated structures...18 S1
2 1 H-NMR and 13 C-NMR spectra Compound 4 (DMS-d 6, 200 MHz): N 2 N H N 2 Because of solubility problems in common deuterated solvents, no 13 C-NMR espectra could be obtained for this compound Compound 5 (DMS-d 6, 200 MHz): N H 2 N H NH 2 S2
3 Compound 6 (DMS-d 6, 200 MHz (proton)/300 MHz (carbon): N NH H NH 2 Compound 7 (DMS-d 6, 200 MHz): N N H H NH HN NH HN S3
4 Compound 8 (DMS-d 6, 200 MHz): N N H H NH HN NH 2 H 2 N Compound 1 (DMS-d 6, 300 MHz): N N H H NH HN NH NH HN HN 2 N N 2 S4
5 Compound 2 (DMS-d 6, 200 MHz (proton)/400 MHz (carbon): N N H H NH HN NH NH HN HN S5
6 UV-Vis spectra 2.5 Absorbance Wavelength (nm) Figure S1. UV-Vis spectrum of receptor 1 in acetonitrile (c = 2x10-5 M, T = 25 ºC). 2 Absorbance Wavelength (nm) Figure S2. UV-Vis spectrum of receptor 2 in acetonitrile (c = 2x10-5 M, T = 25 ºC). S6
7 Titrations in pure acetonitrile 2 Absorbance Wavelength (nm) Absorbance nm nm Equivalents of Guest (A-Ao)Xh Figure S3. UV-Vis titration of 1 with with HP in acetonitrile (c = 2x10-5 M, T = 25 ºC) Absorbance Xh Equivalents of guest Xh (A-Ao)Xh Figure S4. UV-Vis Job plot of 2 with with PPi in HP in acetonitrile at λ = 370 nm (c = 2x10-5 M, T = 25 ºC) S7
8 Figure S5. Fluorescence Job plot of 2 with HP in acetonitrile at λ = 500 nm (c = 2x10-5 M, T = 25 ºC, λ exc = 345 nm) S8
9 Titrations in acetonitrile/water Figure S6. Job plot of the complex [1 HP ] in acetonitrile/water 15% (v/v) (c = 2x10-5 M, T = 25 ºC, λ exc = 345 nm) Water logk 11 error D.L. (M) Content (%) 0 > Table S1. Binding constants and detection limits of receptor 1 towards HP for different water contents Absorbance Exp Fit Absorbance Exp Fit E Concentration of Guest (M) E Concentration of Guest (M) Absorbance E Concentration of Guest (M) Figure S7. Fit plots of the curves corresponding to the complex [1 HP ] with different amounts of water: (from left to right and from top to bottom) 15%, 20% and 30%. (v/v) Exp Fit S9
10 A/Ao Equivalents of Guest Figure S8. Comparison of all the anion tested with 1 in acetonitrile/water 20 % (v/v): 3- HP 2 7 ( ), ATP (-), ADP (+), the rest of anions (acetate, benzoate, 1,3,5- benzenetricarboxylic acid, citrate, phthalate, isophthalate, terephthalate, fluoride, chloride, bromide, iodide, cyanide and azide) are overlapped in the horizontal binding isotherm. Absorbance Wavelength (nm) Figure S9.Evolution of the UV-Vis spectra upon addition of a large excess of HP (only 1, blue line; equiv. of HP red line and equiv. of HP , green line). S10
11 Figure S10. Titration of 1 with HP in the presence of 2 equiv. of acetate, benzoate, trimeaste, citrate, phthalate, isophthalate, terephthalate, fluoride, chloride, bromide, iodide, cyanide and azide. Figure S11. Relative changes in absorbance upon addition of 1 equivalent of HP to receptor 1 in the presence of 10 equivalents of interfering anions in acetonitrile/water 20%. Figure S12. Colour change in the solution of receptor 1 (5x10-5 M in acetonitrile/water 15%) upon addition of 2 equivalents of (from left to right): none, hydrogenpyrophosphate, acetate, benzoate, terephthalate, trimesate, citrate, chloride and dihydrogenphosphate. S11
12 2.5 Absorbance Wavelength (nm) 3- Figure S13. Evolution of absorption spectra of 2 upon titration with HP 2 7 acetonitrile/water 15% (v/v). in Figure S14. Job plot of 2 with HP in acetonitrile/water 15% ([H] = [G] = 2x10-5 M). S12
13 I/Io Equivalents of Guest Figure S15. Comparison of all the anion tested by emission spectroscopy with 2 in 3- acetonitrile/water 15%: HP 2 7 ( ),the rest of anions (acetate, benzoate, trimeaste, citrate, phthalate, isophthalate, terephthalate, fluoride, chloride) are overlapped in the rest of binding isotherms. Figure S16. Fit plot of the curve corresponding to the complex [2 ( HP ) 2 ]. S13
14 NMR titrations 0 eq 0.5 eq 1 eq 1.5 eq 2 eq 3 eq Figure S17. Evolution of the 31 P-NMR spectra of HP in DMS-d 6 upon titration with the receptor 1, using HMPA as external reference. Figure S18. Evolution of 1 H-NMR spectra of 1 at different temperatures upon titration with HP in DMS-d 6. S14
15 Deprotonation tests 0 eq. 0.5 eq. 1 eq. 1.5 eq. 2 eq. 3 eq. Figure S19. Evolution of 1 H-NMR spectra of 1 upon titration with TBAH in DMSd 6. 0 eq. 0.5 eq. 1 eq. 1.5 eq. 2 eq. 3 eq. Figure S20. Evolution of 1 H-NMR spectra of 2 upon titration with TBAH in DMSd 6. S15
16 Emission Intensity (a.u.) Emission Intensity (a.u.) Equivalents of Guest Wavelength (nm) Figure S21. Evolution of emission spectra of 2 upon titration with TBAH in acetonitrile/water 15% (v/v) (c = 2x10-5 M, T = 25 ºC, λ exc = 345 nm) S16
17 NCIplot analyses The reduced density gradient, s (or RDG), derived from the electron density and its first derivative (s = 1/(2(3π2) 1/3 ) ρ /ρ 4/3 ), is a fundamental dimensionless property in DFT used to describe heterogeneous electron distributions. 1 It has large positive values in regions far from the molecule where density decays to zero exponentially but, on the contrary, has very small values (approaching zero) for regions of both covalent and noncovalent interactions. NCIs (non-covalent interactions) can be identified as regions with low ρ and low RDG, originating spikes in RDG vs ρ plots, 2,3 the ρ value of which turns out to be an indicator of the interaction strength. In order to better differentiate among a wide range of weak interactions and especially between stabilizing and destabilizing interactions, the sign of the Laplacian of the density, 2 ρ, must be taken into account by decomposing it into a sum of contributions along the three principal axis of maximal variation, 2 ρ = λ 1 + λ 2 + λ 3 (being λ 1 λ 2 λ 3 ), a criterion widely applied for the analysis of chemical bonding. 4,5 Covalent bonding is characterized by dominant negative contributions of the eigenvalues λ i resulting in an overall negative Laplacian. For weaker interactions (both bonding and nonbonding), the Laplacian is dominated by positive interactions but here the sign of λ 2 is of diagnostic relevance: the interatomic regions of weak bonding interactions can be identified by a negative value of λ 2 whereas nonbonded contacts (steric clashes) feature λ 2 > 0. Consequently, in the RDG plot, the quantity ρ in the horizontal axis is multiplied by the sign of λ 2 (second highest eigenvalue of the electron density Hessian matrix). Vertical spikes approaching the RDG = 0 regime indicate different types of interactions. Those at the positive side of the sign(λ 2 ) ρ axis correspond to nonbonded contacts, whereas at the negative side the bonding interactions are found with the (absolute) value providing information about their strength. S17
18 Figure S22: NCIplot-derived representation of RDG (au) versus sign(λ 2 ) ρ (au) for receptor 1a (blue) and derived 1a HP complex (red). Figure S23: NCIplot-derived representation of RDG (au) versus sign(λ 2 ) ρ (au) for receptor 2a (blue) and derived 2a (H 2 )(K 2 HP 2-7 ) 2 complex (red). Calculated structures. Cartesian coordinates (in Å) and energies for all computed species.- 1a: E = au S18
19 C N H N H N C C C C C C C C C C C C H H H H H H H N C C C C C C C C C C C C H H H H H H H N H C N H C C C C C C H H H H N N H C N H C C C C C C H H H H N a HP : E = au C N H N H N C C C C C C C C C C C C H H H H H H H N C C C C C C C C C C C S19
20 C H H H H H H H N H C N H C C C C C C H H H H N N H C N H C C C C C C H H H H N P P H a: E = au C N H N H N C C C C C C C C C C C C H H H H H H H N C C C C C C C C C C C C H H H H H H H N H C N H N H C N H C C C C C C C C S20
21 C C C C C C C C H H H H H H H H H C C C C C C C C C C C C C C C C H H H H H H H H H a (H 2 )(K 2 HP ) 2 : E = au C N H N H N C C C C C C C C C C C C H H H H H H H N C C C C C C C C C C C C H H H H H H H N H C N H C C C C C C C C C C C C C C C C H H H H H H H H H N H C S21
22 N H C C C C C C C C C C C C C C C C H H H H H H H H H P H P K K P H P K K a (H 2 ) 3 : E = au C N H N H N C C C C C C C C C C C C H H H H H H H N C C C C C C C C C C C C H H H H H H H N H C N H C C C C C C C C C C C C C C C C H H S22
23 H H H H H H H N H C N H C C C C C C C C C C C C C C C C H H H H H H H H H H H H H H H (1) Cohen, A. J.; Mori-Sánchez, P.; Yang, W. Science 2008, 321, 792 (2) Johnson, E. R.; Keinan, S.; Mori-Sánchez, P.; Contreras García, J.; Cohen, A. J.; Yang, W. J. Am. Chem. Soc. 2010, 132, 6498 (3) Contreras García, J.; Johnson, E. R.; Keinan, S.; Chaudret, R.; Piquemal, J.,.P.; Beratan, D. N.; Yang, W. J. Chem. Theory Comput. 2011, 7, 625 (4) Bader, R. F. W. J. Chem. Phys. 1984, 80, 1943 (5) Bader, R. F. W. J. Phys. Chem. A 1998, 102, 7314 S23
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