Redox-Responsive Complexation between a. Pillar[5]arene with Mono ethylene oxide Substituents. and Paraquat

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1 Redox-Responsive Complexation between a Pillar[5]arene with Mono ethylene oxide Substituents and Paraquat Xiaodong Chi, Min Xue, Yong Yao and Feihe Huang* MOE Key Laboratory of Macromolecular Synthesis and Functionalization, Department of Chemistry, Zhejiang University, Hangzhou , P. R. China. Fax: ; Tel: ; address: fhuang@zju.edu.cn. Supporting Information (14 pages) 1. Materials and Methods S2 2. ITC experiments of 1 3 and 2 3 in acetonitrile S2 3. Electrospray ionization mass spectra of hosts 1 and 2 with guest 3 S5 4. A photo showing color changes of redox-responsive complexation between 1 and 3 S6 5 NOESY NMR analysis of 1 3 and 2 3 S7 6 X-ray crystal data for 1 S9 7. X-ray crystal data for 1 3 S9 8. Stoichiomestry determination of 1 3 and 2 3 in acetonitrile S10 9. The Coulomb attractions between the positive charges and the centers of high electron density in the macrocyclic pentagon S References S14 S1

2 1. Materials and Methods: All reagents were commercially available and used as supplied without further purification. Pillar[5]arenes 1 and 2 were synthesized according to a published literature procedure. S1 Solvents were either employed as purchased or dried according to procedures described in the literature. NMR spectra were recorded with a Bruker Avance DMX 500 spectrophotometer or a Bruker Avance DMX 400 spectrophotometer with the deuterated solvent as the lock and the residual solvent or TMS as the internal reference. Low-resolution electrospray ionization (LRESI) mass spectra were obtained on a Bruker Esquire 3000 plus mass spectrometer (Bruker-Franzen Analytik GmbH, Bremen, Germany) equipped with an ESI interface and an ion trap analyzer. UV-vis spectroscopy was performed on a Shimadzu UV-2550 instrument at room temperature. Isothermal titration calorimetric (ITC) measurements were performed on a VP-ITC micro-calorimeter (Microcal, USA). The crystals data were collected on an Oxford Diffraction Xcalibur Atlas Gemini ultra. The crystal structures were solved by SHELXS-97 S2 and refined by SHELXL-97. S3 2. ITC experiments of 1 3 and 2 3 in acetonitrile Isothermal titration calorimetric measurements were performed on a VP-ITC micro calorimeter (Microcal, USA), which is composed of a reference cell and a sample cell of 1.43 ml. Stock solutions of host (0.100 mm, 10.0 ml) and guest (2.00 mm, 5.00 ml) in acetonitrile were prepared using volumetric glassware. Before each titration, all the solutions were degassed and kept constant temperature. In a typical run, a 250 µl syringe was full of guest (2.00 mm) and the cell was loaded with host (0.100 mm, 1.43 ml). The titration of the host with the guest was carried out at 298 K with a constant rate of 307 rpm, 29 injections of 3.3 µl, a time interval of 240 s and a duration of 2 s per μl. The enthalpy change per mole of each added paraquat in the sample cell was recorded continuously. The control titrations of paraquat into acetonitrile were also completed under the same conditions. The enthalpy changes of the titrations of the blank test were subtracted from the original titration. All the data were analyzed with Microcal Origin 7.0 software provided by the manufacturer. The S2

3 final integration data obtained from the titration were fitted by the one set of binding sites model Figure S1. Titration of 1 (0.100 mm) with 3 (2.00 mm) in acetonitrile at 298 K. S3

4 R = Figure S2. Titration of 2 (0.100 mm) with 3 (2.00 mm) in acetonitrile at 298 K. S4

5 3. Electrospray ionization mass spectra of hosts 1 and 2 with guest Figure S3. Electrospray ionization mass spectrum of an equimolar solution of 1 with R = Figure S4. Electrospray ionization mass spectrum of an equimolar solution of 2 with 3. S5

6 4. A photo showing color changes of redox-responsive complexation between 1 and 3 Figure S5. A photo showing color changes of redox-responsive complexation between 1 and 3: (a) 1 alone; (b) equimolar mixture of 1 and paraquat; (c) after addition of 10.0 equiv. of Zn powder to (b); (d) after removal of Zn powder from (d) and exposure to air for two hours; (e) after addition of Zn powder to 1.00 mm 3. S6

7 5. NOESY NMR analysis of 1 3 and 2 3 H 1a H A Figure S6. Partial NOESY NMR analysis of 1 3 (5.00 mm) in CD 3 CN with a mixing time of 800 ms (500 MHz, 298 K). S7

8 H H 2b B H 2a C Figure S7. Partial NOESY NMR analysis of 2 3 (5.00 mm) in CD 3 CN with a mixing time of 800 ms (500 MHz, 298 K). S8

9 6. X-ray crystal data for 1 Crystal data of 1: block, light yellow, C 65 H 90 O 20, FW , monoclinic, space group P 1 a = (4), b = (5), c = (5) Å, = (3), = (2), = (2), V = (19) Å 3, Z = 2, D c = g cm 3, T = 170 K, = mm 1, measured reflections, independent reflections, 384 parameters, 3 restraints, F(000) = , R 1 = , wr 2 = (all data), R 1 = , wr 2 = [I > 2 (I)], max. residual density e Å 3, and goodness-of-fit (F 2 ) = CCDC X-ray crystal data for 1 3 Crystal data of 1 3: block, yellow, C 77 H 104 O 20 F 12 N 2 P 2, FW , monoclinic, space group P 1 a = (6), b = (8), c = (8) Å, = (4), = (4), = (4), V = (3) Å 3, Z = 2, D c = g cm 3, T = 170 K, = mm 1, measured reflections, independent reflections, 1030 parameters, 3 restraints, F(000) = , R 1 = , wr 2 = (all data), R 1 = , wr 2 = [I > 2 (I)], max. residual density e Å 3, and goodness-of-fit (F 2 ) = CCDC S9

10 Absorption Intensity 8. Stoichiomestry determination of 1 3 and 2 3 in acetonitrile Wavelength nm S10

11 R 2 = [H] 0 / [G] 0 R 2 = Absorption Intensity Figure S8 The absorption spectral changes of 1 (0.500 mm) upon addition of 3 (5.00 mm) (top) and mole ratio plot (bottom) for the complexation between 1 and 3, indicating a 1:1 stoichiometry. S11

12 Absorption Intensity Wavelength nm R 2 = [H] 0 / [G] 0 R 2 = Absorption Intensity Figure S9 The absorption spectral changes of 2 (0.500 mm) upon addition of 3 (5.00 mm) (top) and mole ratio plot (bottom) for the complexation between 2 and 3, indicating a 1:1 stoichiometry. S12

13 10. The Coulomb attractions between the positive charges and the centers of high electron density in the macrocyclic pentagon M R V Q N S P O U T Figure S10. Ball-stick views of the crystal structure of 1 3. Host 1 is red, guest 3 is blue, hydrogen atoms are sky blue, oxygen atoms are green, and nitrogen atoms are black. PF 6 counterions, solvent molecules and hydrogens except the ones involved in hydrogen bonding were omitted for clarity. Blue dashed lines indicate the Coulomb attractions between the positive charges and the centers of high electron density in the macrocyclic pentagon (M V). The Coulomb attraction parameters: the Coulomb attraction distances (Å): M, 5.70; N, 6.15; O, 6.05; P, 5.82; Q, 4.65; R, 5.16; S, 4.69; T, 4.93; U, 5.82; V, A reviewer of this paper said that these Coulomb attractions are important for the stabilization of this complex and asked us to list the related distances. Therefore, these related distances are listed here. S13

14 References: S1. Ogoshi, T., Shiga, R., Yamagishi, T., J. Am. Chem. Soc. 2012, 134, S2. Sheldrick, G. M. SHELXS-97, Program for solution of crystal structures, University of Göttingen, Germany, S3. Sheldrick, G. M. SHELXS-97, Program for refinement of crystal structures, University of Göttingen, Germany, S14

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