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1 Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique Singular Supramolecular Self-assembling of Bis-Cyclodextrinyl-Bis-Lariat Hosts with Bis-Aryl- Sulfonates as Guests Florence Dumarçay-Charbonnier, * Jean Pierre Joly and Alain Marsura* UMR CNRS SRSMC Faculté des Sciences et Technologies. Université de Lorraine, BP, Vandœuvre-lès-Nancy, France. alain.marsura@univ-lorraine.fr; Tel :+. General procedures. Characterization of the products. NMR Spectra Supporting Information. General procedures Chemicals and solvents (reagent grade or better) were purchase from Sigma-Aldrich. Anhydrous solvents were dried by usual procedures and stored over Å molecular sieves under Ar before use. Chromatography was carried out using Grace silicagel. H and C-NMR spectra were recorded on a Bruker DRX FT-NMR spectrometer at MHz for H and MHz for C. Chemicals shifts were reported in parts per million (ppm), calibrated to the residual solvent peak set, with coupling constants reported in Hertz (Hz). High Resolution Electrospray (HR-ESIMS) and (MALDI-TOF) Mass spectra were recorded on a Bruker MicroQ-TOF and a Bruker Daltonics Reflex IV spectrometer respectively. FT-IR spectra were obtained from KBr pellets on a perkin Elmer Spectrum photometer. Zn II, Cu II and Ca II bis-tosylates, Zn II and Cu II bis-sulfanilate salts were obtained by a slightly modified method of the literature. Synthesis of the chiral bis- -cyclodextrinyldiazacrown receptor see. Synthesis of the achiral bis- cyclodextrinyl-diazacrown receptor see. General procedure for pseudo-rotaxane preparation equiv. of metal bis-tosylate or bis-sulfanilate salt is added to equiv. of dimer, or in water (ml) at r.t. The solution is stirred overnight at r. t., evaporated to dryness and then lyophilised.. Characterization of the products [bis-triazolo-peracetylated- -cyclodextrinyl]-diaza-[-]-crown To a stirred solution of N,N -bis-propargyl-diaza-[-]-crown ( mg,, mmol,. g.mol - ) in CH Cl at r.t. are added mono-azido peracetylated -cyclodextrin ( mg,. g.mol -,. equiv.), Na-ascorbate ( mg,. equiv.) and CuSO. H O (.mg,. equiv.) under argon. The yellow pale mixture is stirred overnight and evaporated. The crude material is purified by chromatography on silicagel with CH Cl /MeOH gradient as eluent. The final product is obtained as a white powder in % yield. H NMR (MHz, CDCl, K): =. (s, H; Triazol H),. (s, H; H),.-. (m, H ; H, H, H, H, H, H ),.-. (m; CH crown),.-. (m; H, CH crown),. (bs, H; CH triazol),.-. (m, H; CH -CO). C NMR (MHz, CDCl, K): = (CH CO),. (CH -C=C-N triazol)),. (CH triazol) (C), (C), (C, C, C), (CH crown), (C),. (N-CH -C=C triazol), (CH crown),. (C ),. (CH crown),. (CH -CO). [bis-triazolo- -cyclodextrinyl]-diaza-[-]-crown NH is bubbling during hours through a solution of (.mg,. mmol,. g.mol-) in anhyd. MeOH. The solution is stirred into the MeOH /NH saturated solution during or days. The mixture is then evaporated to dryness, lyophilised to give in a quantitative yield as flocculent white solid. H NMR (MHz, D O, K): =. (s, H, TriazolH),. (s, H; CH crown),. (s,h; H ),. (b s; CH crown),.-. (m, H; CH crown),.-. (m, H; H, H, H, H, H, H ),.-. (m; CH crown),.-. (m; CH crown),.-. (m; CH crown),. (s, H; CH triazol). C NMR (MHz, D O, K): =. (CH triazol),. (C),. (C),.-.-. (C, C, C),. (C),. (C ),. (CH triazol), (CH crown),. (CH triazol),. (CH crown),. (CH crown). ESIMS: m/z:. [M/+H + ]. Pseudo-[]rotaxane [bis- -cyclodextrinyl]-diaza-[-]-crown dimer (mg,, mmol, M =, g.mol - ). Zn II p-tosylate (, mg,,. - mmol, M=, g.mol - ). was obtained quantitatively as a pale white flocculent solid. IR (KBr): = (OH), (CH- ), (CH arom.), (C=O urea) cm -. H NMR (MHz, D O, K): =. (d, J (H,H)=Hz, H; Har),. (d, J (H,H)=Hz, H; Har),. (s, H; H),. (d, J (H,H) = Hz, H; CH crown),. (bs, H; H ),.-. (m, H; CH crown),.-. (m, H; CH crown),.-. (m, H; CH crown),.-. (m, H; H, H, H, H, H, H ),.-. (m, H; CH crown). C NMR (MHz, D O, K): =. (C=O; urea),. (q),. (q),. (CH arom.),. (CH arom.),. (C),. (C),. (CH crown),. (CH crown),. (CH crown),. (CH crown),.-.-. (C, C, C),. (C). (CH crown),. (CH crown),. (C ),. (CH crown),. (CH crown),. (CH crown),. (CH Ph). Maldi-TOF [C H N O S Zn:.u.m.a.],. [M- Zn(OTs) ]
2 Pseudo-[]rotaxane [bis- -cyclodextrinyl]-diaza-[-]-crown dimer (mg,, mmol, M =, g.mol - ). Cu II p-tosylate (,mg,,. - mmol, M=, g.mol - ). was obtained quantitatively as a pale green flocculent solid. IR (KBr): (OH) (CH-) (CH arom.), (C=O urea) cm -. H NMR (MHz, D O, K): =. (d, J(H,H)=Hz, H; Har),. (d, J(H,H)=Hz, H; Har),. (bs, H; H),. (s, H; CH - crown),. (s, H; H ),. (m, H; CH crown),.-. (m, H; H, H, H, H, H, CH crown),.-. (m, H; CH crown),. (s, H; CH -Ph). C NMR (MHz, D O, K): =. (C=O urea),. (q),. (q),. (CH arom.),. (CH arom.),. (C),. (C),. (CH crown),. (CH crown),. (CH crown),. (CH crown),. (C),. (C),. (CH crown),.-.-. (CH crown),. (C),.-. (CH crown),. (C),. (C),. (CH crown),. (C ),.-.,. (CH crown),. (CH ) Maldi-TOF [C H CuN O S :. u.m.a.]:. [M-Cu(OTs) +Cu],. [M-Cu(OTs) ]. Pseudo-[]rotaxane [bis- -cyclodextrinyl]-diaza-[-]-crown dimer (mg,, mmol, M =, g.mol - ). Ca II p-tosylate (, mg,,. - mmol, M=, g.mol - ). was obtained quantitatively as a pale white flocculent solid. H NMR (MHz, D O, K) =. (d, J(H,H)=Hz, H; Har),. (d, J(H,H)=Hz, H; Har),. (s, H, CH crown),. (d, J(H,H)=Hz,H; CH crown),. (bs, H; H),.-. (m, H; CH crown),.-. (m, H; CH crown),.-. (m, H; H, H, H, H, H, H ),.-. (m, H; CH crown). C NMR (MHz, D O, K): =. (C=O urea),. (q),. (q),.(ch arom.),. (CH arom.),. (C),. (CH crown),. (CH crown),. (CH crown),. (CH crown),. (CH crown),.-.-. (C, C, C),. (C). (CH crown),. (CH crown),. (C ),. (CH crown),. (CH crown),. (CH crown),. (CH ). Maldi-TOF [C H CaN O S :.u.m.a.]:. [M- Ca(OTs) ]. Pseudo-rotaxane [bis- -cyclodextrinyl]-diaza-[-]-crown dimer (mg,, mmol, M =. g.mol - ). Zn II p-tosylate (. mg,,. - mmol, M=. g.mol - ). was obtained quantitatively as a white flocculent solid. IR (KBr): (OH), (CH-), (CHar), (C=O urea) cm -. H NMR (MHz, D O, K): =. (d, J(H,H)=Hz, H; Har),. (d, J(H,H)=Hz, H; Har),. (s, H; H),.-. (m, H; H, H, H, H, H, H, CH crown),. (s, H, CH ). C NMR (MHz, D O, K): =. (C=O urea),. (q),. (q),. (CH arom.),. (CH arom.),. (C),. (C), (C, C, C, C) (C),. (C),. (C ),. (CH crown),. (CH crown),. (CH ). Maldi-TOF [C H N O S Zn:. u.m.a.]:. [M- Zn(OTs) +H + ] Pseudo-[]rotaxane [bis- -cyclodextrinyl]-diaza-[-]-crown dimer (mg,, mmol, M =. g.mol - ). Cu II p-tosylate (, mg,,. - mmol, M=, g.mol - ). was obtained quantitatively as a pale green flocculent solid. IR (KBr): (OH), (CH- ), (CHar), (C=O urea) cm -. H NMR (MHz, D O, K) =. (d, J(H,H) = Hz, H; Har),. (d, J(H,H) = Hz, H; Har),. (s, H; H),.-. (m, H; H, H, H, H, H, H, CH crown),. (s, H, CH ). C NMR (MHz, D O, K): =. (C=O urea),. (q),. (q),. (CH arom.),. (CH arom.),. (C),. (C),.,.,.,., (C, C, C, C),. (C),. (C ),. (CH crown),. (CH crown),. (CH ). Maldi-TOF [C H CuN O S :. u.m.a.]:. [M-Cu(OTs) ],. [M-Cu(OTs) +Cu]; ESIMS: m/z :.[M/+H + ],.[M-Cu(OTs) +Cu+OTs],. [M+H + ] Pseudo-[]rotaxane [bis- -cyclodextrinyl]-diaza-[-]-crown dimer (mg,, mmol, M =. g.mol - ). Ca II -p-tosylate (. mg,,. - mmol, M=. g.mol - ). was obtained quantitatively as an off-white flocculent solid. IR (KBr): (OH), (CH-), (CHar), (C=O urea), cm -. H NMR (MHz, D O, K): =. (d, J(H,H) = Hz, H; Har),. (d, J(H,H) = Hz, H; Har),. (s, H; H),.-. (m, H H, H, H, H, H, H, CH crown),. (s, H; CH ). C NMR (MHz, D O, K): =. (C=O urea),. (q),. (q),. (q),. (q),. (C),. (C),.,.,.,.,. (C, C, C, C) (C),. (C),. (C ),. (CH crown),. (CH crown),. (CH ). Maldi-TOF [C H CaN O S :. u.m.a.]:. [M- Ca(OTs) ] Pseudo-[]rotaxane [bis- -cyclodextrinyl]-diaza-[-]-crown dimer (mg,, mmol, M =, g.mol - ), Zn II bis-sulfanilate (. mg,,. - mmol, M=. g.mol - ) was obtained quantitatively as a white solid. IR (KBr): (OH), (CH-), (CHar), (C=O urea) cm -. H NMR (MHz, D O, K): =. (d, J (H,H) = Hz, H; Har),. (d, J (H,H) = Hz, H; Har),. (s, H; H),. (d, J (H,H) = Hz, H; CH crown),. (bs, H; H),. (d, J (H,H) = Hz, H; CH crown),.-. (m, H; CH crown),.-. (m, H; H, H, H, H, H, H, CH crown),.-. (m, H, CH crown). C NMR (MHz, D O, K): =. (C=O urea),. (q),. (q),.(ch arom.),. (CH arom.),. (C),. (C),. (CH crown),. (CH crown),. (CH crown),. (CH crown),.,.,. (C, C, C),. (C). (CH crown),. (CH crown),. (C ),. (CH crown),. (CH crown),. (CH crown). Maldi-TOF [C H N O S Zn:.u.m.a.]:. [M- Zn(NH PhSO ) +H + ] Pseudo-[]rotaxane [bis- -cyclodextrinyl]-diaza-[-]-crown dimer (mg,, mmol, M =, g.mol - ). Ca II bis-sulfanilate (. mg,,. - mmol, M= g.mol - ). was obtained quantitatively as a white solid. IR (KBr): (OH), (CH-), (CH arom.), (C=O urea) cm -. H NMR (MHz, D O, K): =. (d, J =(H,H) = Hz, H; CH arom.),. (d, J(H,H) = Hz, H; Har),. (s, H; H),. (d, J(H,H) = Hz, H; CH crown),. (bs, H; H),. (d, J (H,H) = Hz, H; CH crown),.-. (m, H; CH crown),.-. (m, H; H, H, H, H, H, H, CH crown),.-. (m, H; CH crown). C NMR (MHz, D O, K) =. (CO urea),. (q). (q),.(ch arom.),. (CH arom.),. (C),. (C),. (CH crown),. (CH crown),. (CH crown),. (CH crown),.,.,. (C, C, C),. (C). (CH crown),. (CH crown),. (C ),. (CH crown),. (CH crown),. (CH crown). Maldi-TOF [C H CaN O S :. u.m.a.]:.[m- Ca(NH PhSO ) +H + ] Pseudo-rotaxane Bis-triazolo- -cyclodextrinyl-diaza-[-]-crown dimer (mg,, mmol, M =. g.mol - ). Zn II bis-sulfanilate (. mg,,. - mmol, M=. g.mol - ) in water, was obtained quantitatively as a white solid. IR (KBr): (OH) (CH-) (CH arom.), (C=O urea) cm -. H NMR (MHz, D O, K): =. (s, H; TriazolH),. (d, J (H,H)=Hz, H; Har),. (d, J (H,H)=Hz, H; Har),. (s, H; CH crown),. (s,h; H ),. (b s; CH crown),. (m, H; CH crown),. (m; CH crown),.-. (m, H;
3 H, H, H, H, H, H ),.-. (m; CH crown),.-. (m; CH crown),.-. (m; CH crown),. (s, H; CH triazol). C NMR (MHz, D O, K): =. (CH arom.),. (CH triazol),. (CH arom.),. (C),. (C),.-.-. (C, C, C),. (C),. (C ),. (CH triazol),. (CH crown),. (CH triazol),. (CH crown),. (CH crown). Maldi-TOF [C H N O S Zn:. u.m.a.]:. [M- Zn(NH PhSO ) +H + ]. NMR Spectra Pseudo-[]rotaxane D NMR (ROESY) H arom H arom CH -Ph H,H H,H Pseudo-[]rotaxane D NMR (ROESY) H arom H,H H,H
4 C NMR SPECTRA Pseudorotaxane : C FDIV...r.esp - Pseudorotaxane C FDIV_r.esp -
5 Pseudorotaxane : FDIV...r.esp - Pseudorotaxane : C FDIV_r.esp -
6 Pseudorotaxane : C FDIV complète...r.esp - Pseudorotaxane : FDIV...r.esp -
7 Pseudorotaxane : FDIV...r.esp - Pseudorotaxane : FDIV...r.esp -
8 Job plots of pseudo[]rotaxanes to NB : job plots of and : are not given because of less amount of starting the chiral dimer material. Pseudo[]rotaxane Variation of CD H protons Variation of tosylate aromatic protons
9 Pseudo[]rotaxane : Variation of CD H protons Variation of tosylate aromatic protons
10 Pseudo[]rotaxane : Variation of CD H protons Variation of tosylate aromatic protons
11 Pseudo[]rotaxane : Variation of tosylate aromatic protons Variation of CD H protons
12 pseudorotaxane Titration of with Zn II bisulfanilate sur Ka pente.. ord ori.e- Ka = M - Variation of sulfanilate aromatic protons
13 Pseudo[]rotaxane : Variation of CD H protons Variation of sulfanilate aromatic protons
14 Pseudo[]rotaxane : Titration of with Zn II bisulfanilate : sur Ka pente.. ord ori.e-.. Ka = M -
15 References S. Menuel, J.-P. Joly, B. Courcot, J. Elysée, N. E. Ghermani and A. Marsura, Tetrahedron,,, -. S. Porvanski, F. Dumarcay-Charbonnier, S. Menuel, V. Bulach, J.-P. Joly and A. Marsura, Tetrahedron,,, -. Xu-Jie, Yang, X. Wang, D.-Y. Chen, J. Yang, L.-D. Lu, X.-Q. Sun, G.-Y. He and J. Chen, J. of Applied Polymer Science,,, -.
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