Syntheses and Characterizations of Molecular Hexagons and Rhomboids and Subsequent Encapsulation of Keggin-Type Polyoxometalates by Molecular Hexagons
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1 Supporting Information for Syntheses and Characterizations of Molecular Hexagons and Rhomboids and Subsequent Encapsulation of Keggin-Type Polyoxometalates by Molecular Hexagons Kazuhiro Uehara, Takamichi Oishi, Takayuki Hirose, and Noritaka Mizuno* Department of Applied Chemistry, School of Engineering, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo , Japan Contents Details of X-ray Crystallography Details of DFT calculations Figure S1. IR spectrum of [(en)pd(l)] 3 (OTf) 6 1t OTf (KBr, cm 1 ) Figure S2. IR spectrum of [(en*)pd(l)] 2 (PF 6 ) 4 2d PF 6 (KBr, cm 1 ) Figure S3. IR spectrum of {[(dppe)pd(l)](otf) 2 } 3 OTf (KBr, cm 1 ) Figure S4. IR spectrum of [(en*)pd(l)] 3 [ α-pw 12 O 40 ](NO 3 ) 3 S3 S4 S14 S15 S16 S17 Figure S5. CSI-MS spectrum of {[(dppe)pd(l)](otf) 2 } 3 OTf (263 K, MeCN) S18 Figure S6. NMR spectra of [(en)pd(l)] 3 (OTf) 6 1t OTf in DMSO-d 6, (a) 1 H line (500 MHz), 13 C{H} line ( MHz), and (c) 19 F line ( MHz) S19 Figure S7. NMR spectra of [(en*)pd(l)] 2 (PF 6 ) 4 2d PF 6 in DMSO-d 6, (a) 1 H line (500 MHz), (b) 13 C{H} line ( MHz), (c) 31 P{H} line ( MHz), and (d) 19 F line ( MHz). S21 Figure S8. NMR spectra of {[(dppe)pd(l)](otf) 2 } 3 OTf in DMSO-d 6, (a) 1 H line (500 MHz), (b) 13 C{H} line ( MHz), (c) 31 P{H} line ( MHz) and (d) 19 F line ( MHz) Figure S9. 1 H DOSY spectrum of [(en)pd(l)] n (OTf) 2n 1t/1d OTf (n = 2, 3) (DMSO-d 6, 303 S23 S1
2 K) S25 Figure S10. Curve fitting analysis of 1 H DOSY NMR for [(en)pd(l)] 3 (OTf) 6 1t OTf Figure S11. Curve fitting analysis of 1 H DOSY NMR for [(en)pd(l)] 2 (OTf) 4 1d OTf S26 S27 Figure S12. Curve fitting analysis of 19 F DOSY NMR for [(en)pd(l)] n (OTf) 2n 1t/1d OTf (n = 2, 3) S28 Figure S13. 1 H DOSY spectrum of [(en*)pd(l)] n (PF 6 ) 2n 2t/2d PF 6 (n = 2, 3) (DMSO-d 6, 303 K) S29 Figure S14. Curve fitting analysis of 1 H DOSY NMR for [(en*)pd(l)] 2 (PF 6 ) 4 2t PF 6 S30 Figure S15. Curve fitting analysis of 1 H DOSY NMR for [(en*)pd(l)] 2 (PF 6 ) 4 2d PF 6. S31 Figure S16. Curve fitting analysis of 31 P DOSY NMR for [(en*)pd(l)] n (PF 6 ) 2n 2t/2d PF 6 S32 Figure S17. Curve fitting analysis of 1 H DOSY NMR for {[(dppe)pd(l)] 2 (OTf) 2 } 3 OTf S33 Figure S18. Curve fitting analysis of 19 F DOSY NMR for {[(dppe)pd(l)] 2 (OTf) 2 } 3 OTf S34 Figure S19. 1 H DOSY spectrum of [(en*)pd(l)] n (PF 6 ) 2n 2t/2d PF 6 (n = 2, 3) in the presence of H 3 [α-pw 12 O 40 ] (DMSO-d 6, 303 K) S35 Figure S20. Curve fitting analysis of 1 H DOSY NMR for {[(en*)pd(l)] 3 [[ α-pw 12 O 40 ]](PF 6 ) 3 2t [α-pw 12 O 40 ] 3 S36 Figure S21. Curve fitting analysis of 1 H DOSY NMR for {[(en*)pd(l)] 2 [α-pw 12 O 40 ]}(PF 6 ) 2d [α-pw 12 O 40 ] 3 S37 Figure S22. Curve fitting analysis of 31 P DOSY NMR for {[(en*)pd(l)] 3 [ α-pw 12 O 40 ]}(PF 6 ) 3 2t [α-pw 12 O 40 ] 3 S38 Figure S23. Curve fitting analysis of 31 P DOSY NMR for H 3 [α-pw 12 O 40 ] S39 References S40 S2
3 Details of X-ray crystallography. Diffraction measurements for 1t OTf, 2d PF 6, and 3 W 6 O 19 were made on Rigaku MicroMax-007 with Mo Kα radiation (λ = Å). The data collections were carried out at 153 K. Indexing was performed from 12 oscillation images, which were exposed for 5 s. The crystal-to-detector distance was 45 mm. Readout was performed with the pixel size of mm. A sweep of data was done using ω scans from 110 to 70 at κ = 45 and φ = 0, 90. A total of 720 images for each compound were collected. Neutral scattering factors were obtained from the standard source. 1 Data were corrected for Lorentz and polarization effects. Empirical absorption corrections were made with HKL 2000 for Linux. 2 Molecular structures were solved by SHELX-97 3 linked to Win-GX for Windows 4. Total of six and four anions for 1t OTf and 2d PF 6 were confirmed, but highly disordered. Therefore, the SQUEEZE program of PLATON was used to remove the electron density on the Fourier map derived from the disordered solvents of crystallization. 5 Cationic parts for 1t OTf, 2d PF 6, and 3 W 6 O 19 were refined anisotropically. Tungsten atoms of hexatungstate in 3 W 6 O 19 were refined anisotropically, whereas oxygen atoms of hexatungstate in 3 W 6 O 19 were refined isotropically. Hydrogen atoms for 1t OTf, 2d PF 6, and 3 W 6 O 19 were refined as a riding model. As for 3 W 6 O 19, parts of phenyl groups of dppe ligand in 3 W 6 O 19 were disordered. The disordered atom sets were (C21A C26A, C21B C26B) and (C61A C66A, C61B C66B), and the respective occupancies were 0.51, 0.49) and (0.39, 0.61), respectively. Hydrogen atoms for these parts were not refined. Crystallographic data for compounds 1t OTf (CCDC ), 2d PF 6 (CCDC ), and 3 W 6 O 19 (CCDC ) are available free of charge from the Cambridge Crystallographic Data Center. S3
4 Details of DFT calculations DFT calculations were performed with Gaussian 09 software. Cationic parts of 1t OTf and 2h PF 6 were optimized using 6-31G* (C, H, N) /LanL2DZ (Pd) (6D, 7F) with B3LYP level of theory, taking into account the solvation in DMSO with the conductor-like polarizable continuum model (IEFPCM) with the parameter sets of United Atom Topological Model (UAKS). The corresponding single-point energy calculation was carried out using G** (C, H, N) / LanL2DZ (Pd) basis sets with B3LYP level of theory, taking into account the solvation in DMSO with the conductor-like polarizable continuum model (IEFPCM) with the parameter sets of United Atom Topological Model (UAKS). Cartesian coordinates of [(en)pd(l)] 4+ 2 in DMSO. C 1 symmetry Hartree hartree (single-point) Pd C Pd H N C N H N C N C C C H C C H H C C C H C S4
5 C C H H C C H C C H C C N H C C H H C C H C C N C C H H C C H H C C H C H H C C H H H N N C C H H H C C H C C C C H H H C H H H H H H H S5
6 H H Cartesian coordinates of [(en*)pd(l)] 4+ 2 in DMSO. C 1 symmetry hartree hartree (single-point) Pd H Pd C N C N H N C N H C C H H C C H C C N C H H C C H H C C C C C H C C H C C C H H S6
7 H C H C C H H C H H H C C H H C H C C N H C H H C C H H H C H C C H H C H H H C N H C H H H C N H C C H C H H H C C H H H H C H H C H C S7
8 H C C H H H Cartesian coordinates of [(en)pd(l)] 6+ 3 in DMSO C 1 symmetry hartree hartree (single-point) Pd H N N C H H H C N H H C H C N H C C H C C H C C H C C H H C N S8
9 H H C H C N C H C H H N C C H H C C H H C C C C H H C C C H C C H C H C C C H H H C Pd H N C C H H C C C H H C C C H C C H C H C C C H H S9
10 H C Pd H N C C H H C C C H H C C C C H C C H H H N C H H H H N C H H H C N C C H H Cartesian coordinates of [(en*)pd(l)] 6+ 3 in DMSO. C 1 symmetry hartree hartree (single-point) S10
11 Pd C N C C H H C C H H C C H C C H C C H H C N C N C N H C H H C C H H H C Pd C N H C C H H C C H C C N C N H C C H C C N H C C H C C H H S11
12 C C H C C H C C C H C N H N C N H C C H H C C H C C H C C H C C C H H C H C C C H C H H Pd C N H C C H H C H C H H C C H C H C H H C H H S12
13 C H H H H C C H H H H H H C C H H H H H H C C H H H H H H C C H H H H H H H C H H S13
14 Figure S1. IR spectrum of [(en)pd(l)] 3 (OTf) 6 1t OTf (KBr, cm 1 ). S14
15 Figure S2. IR spectrum of [(en*)pd(l)] 2 (PF 6 ) 4 2d PF 6 (KBr, cm 1 ). S15
16 Figure S3. IR spectrum of {[(dppe)pd(l)](otf) 2 } 3 OTf (KBr, cm 1 ). S16
17 Figure S4. IR spectrum of [(en*)pd(l)] 3 [[ α-pw 12 O 40 ](NO 3 ) 3. S17
18 Figure S5. CSI-MS spectrum of {[(dppe)pd(l)](otf) 2 } 3 OTf (263 K, MeCN) S18
19 Figure S6. NMR spectra of [(en)pd(l)] 3 (OTf) 6 1t OTf in DMSO-d 6, (a) 1 H line (500 MHz), 13 C{H} line ( MHz), and (c) 19 F line ( MHz). S19
20 Figure S6. (Continued) S20
21 Figure S7. NMR spectra of [(en*)pd(l)] 2 (PF 6 ) 4 2d PF 6 in DMSO-d 6, (a) 1 H line (500 MHz), (b) 13 C{H} line ( MHz), (c) 31 P{H} line ( MHz), and (d) 19 F line ( MHz). S21
22 Figure S7. (Continiued) S22
23 Figure S8. NMR spectra of {[(dppe)pd(l)](otf) 2 } 3 OTf in DMSO-d 6, (a) 1 H line (500 MHz), (b) 13 C{H} line ( MHz), (c) 31 P{H} line ( MHz) and (d) 19 F line ( MHz). S23
24 Figure S8. (Continitued) S24
25 Figure S9. 1 H DOSY spectrum of [(en)pd(l)] n (OTf) 2n 1t/1d OTf (n = 2, 3) (DMSO-d 6, 303 K). S25
26 Figure S10. Curve fitting analysis of 1 H DOSY NMR for [(en)pd(l)] 3 (OTf) 6 1t OTf S26
27 Figure S11. Curve fitting analysis of 1 H DOSY NMR for [(en)pd(l)] 2 (OTf) 4 1d OTf. S27
28 Figure S12. Curve fitting analysis of 19 F DOSY NMR for [(en)pd(l)] n (OTf) 2n 1t/1d OTf (n = 2, 3). S28
29 Figure S13. 1 H DOSY spectrum of [(en*)pd(l)] n (PF 6 ) 2n 2t/2d PF 6 (n = 2, 3) (DMSO-d 6, 303 K). S29
30 Figure S14. Curve fitting analysis of 1 H DOSY NMR for [(en*)pd(l)] 2 (PF 6 ) 4 2t PF 6. S30
31 Figure S15. Curve fitting analysis of 1 H DOSY NMR for [(en*)pd(l)] 2 (PF 6 ) 4 2d PF 6. S31
32 Figure S16. Curve fitting analysis of 31 P DOSY NMR for [(en*)pd(l)] n (PF 6 ) 2n 2t/2d PF 6 S32
33 Figure S17. Curve fitting analysis of 1 H DOSY NMR for {[(dppe)pd(l)] 2 (OTf) 2 } 3 OTf. S33
34 Figure S18. Curve fitting analysis of 19 F DOSY NMR for {[(dppe)pd(l)] 2 (OTf) 2 } 3 OTf. S34
35 Figure S19. 1 H DOSY spectrum of [(en*)pd(l)] n (PF 6 ) 2n 2t/2d PF 6 (n = 2, 3) in the presence of H 3 [α-pw 12 O 40 ] (DMSO-d 6, 303 K). S35
36 Figure S20. Curve fitting analysis of 1 H DOSY NMR for {[(en*)pd(l)] 3 [[ α-pw 12 O 40 ]](PF 6 ) 3 2t [α-pw 12 O 40 ] 3. S36
37 Figure S21. Curve fitting analysis of 1 H DOSY NMR for {[(en*)pd(l)] 2 [α-pw 12 O 40 ]}(PF 6 ) 2d [α-pw 12 O 40 ] 3. S37
38 Figure S22. Curve fitting analysis of 31 P DOSY NMR for {[(en*)pd(l)] 3 [ α-pw 12 O 40 ]}(PF 6 ) 3 2t [α-pw 12 O 40 ] 3. S38
39 Figure S23. Curve fitting analysis of 31 P DOSY NMR for H 3 [α-pw 12 O 40 ]. S39
40 References (1) International Tables for X-ray Crystallography, Kynoch Press, Birmingham, U.K., 1975, Vol. 4. (2) Otwinowski, Z.; Minor, W. Processing of X-ray Diffraction Data Collected in Oscillation Mode, Methods in Enzymology, Macromolecular Crystallography, Part A (Eds: C. W. Carter, Jr., R. M. Sweet), Academic Press, New York, 1997, Vol. 276, p (3) Sheldrick, G. M. SHELX-97, Programs for Crystal Structure Analysis, release 97 2, University of Göttingen: Göttingen, Germany, (4) Farrugia, L. J. J. Appl. Crystllogr. 1999, 32, (5) Spek, A. L. J. App. Cryst. 2003, 33, (6) Complete Ref. 30: Gaussian 09, Revision B.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian, Inc., Wallingford CT, (7) Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, (8) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, (9) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, (10) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, S40
41 (11) Becke, A. D. J. Chem. Phys. 1993, 98, (12) Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77, (13) Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1997, 78, (14) Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, S41
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