Photo-Induced Self-Assembly of Pt(II)-Linked Rings and Cages via the Photolabilization of a Pt(II) Pyridine Bond
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1 Photo-Induced Self-Assembly of Pt(II)-Linked Rings and Cages via the Photolabilization of a Pt(II) Pyridine Bond Ken-ichi Yamashita, Kei-ichi Sato, Masaki Kawano and Makoto Fujita* Contents; Figure S1. 1 H NMR observation of the self-assembly from ligand 4a by UV irradiation. Figure S2. Figure S3. Figure S4. Figure S5. Figure S6. 1 H NMR observation of the self-assembly from ligand 4b by UV irradiation. 1 H NMR observation of the self-assembly from ligand 4c by UV irradiation. 1 H NMR observation of the self-assembly from ligand 2b by UV irradiation. 1 H NMR observation of the self-assembly from ligand 2c by UV irradiation. 1 H NMR observation of the self-assembly from ligand 2a after heating at 80 ºC without UV irradiation. Figure S7. Frontier energy level scheme and some related molecular orbitals for [(en)pt(4a)] 8+ 4, as calculated using DFT. Figure S8. Frontier energy level scheme and some related molecular orbitals for [(en)pt(4b)] 6+ 3, as calculated using DFT. Figure S9. Frontier energy level scheme and some related molecular orbitals for [(en)pt(4c)] 6+ 3, as calculated using DFT. Figure S10. Frontier energy level scheme and some related molecular orbitals for [(en)pt(4d)] 6+ 3, as calculated using DFT. Table S1. Cartesian Coordinates of [(en)pt(4a)] 8+ 4 optimized using the B3LYP level of the theory with the LANL2DZ basis set for Pt, and 6-31G* for the other atoms, respectively. Table S2. Cartesian Coordinates of [(en)pt(4b)] 6+ 3 optimized using the B3LYP level of the theory with the LANL2DZ basis set for Pt, and 6-31G* for the other atoms, respectively. Table S3. Cartesian Coordinates of [(en)pt(4c)] 6+ 3 optimized using the B3LYP level of the theory with the LANL2DZ basis set for Pt, and 6-31G* for the other atoms, respectively. Table S4. Cartesian Coordinates of [(en)pt(4d)] 6+ 3 optimized using the B3LYP level of the theory with the LANL2DZ basis set for Pt, and 6-31G* for the other atoms, respectively. Table S5. Cartesian Coordinates of 4b optimized using the B3LYP level of the theory with the 6-31G* for all atoms. Table S6. Cartesian Coordinates of 4d optimized using the B3LYP level of the theory with the 6-31G* for all atoms. Table S7. Crystal data and structure refinement for 5 (H 2 O) m. Figure S11. ORTEP views (30% probability level) of 9 (H 2 O) m. Water molecules and nitrate anions are severely disordered. 1
2 Figure S1. 1 H NMR observation of the self-assembly from ligand 4a by UV irradiation (Aromatic region, 500 MHz, D 2 O/1,4-dioxane-d 8 1:1): (a) before irradiation, and after irradiation for (b) 1 h, (c) 3 h, and (d) 6 hours. 2
3 Figure S2. 1 H NMR observation of the self-assembly from ligand 4b by UV irradiation (500 MHz, D 2 O/1,4-dioxane-d 8 1:1): (a) before irradiation, and after irradiation for (b) 15 min, (c) 60 min, and (d) 240 min. 3
4 Figure S3. 1 H NMR observation of the self-assembly from ligand 4c by UV irradiation (500 MHz, D 2 O/1,4-dioxane-d 8 1:1): (a) before irradiation, and after irradiation for (b) 30 min, (c) 60 min, (d) 90 min, and (e) 120 min. 4
5 Figure S4. 1 H NMR observation of the self-assembly from ligand 2b by UV irradiation (500 MHz, D 2 O/1,4-dioxane-d 8 1:1): (a) before irradiation, and after irradiation for (b) 15 min, (c) 30 min, (d) 60 min, and (e) 120 min. 5
6 Figure S5. 1 H NMR observation of the self-assembly from ligand 2c by UV irradiation (500 MHz, D 2 O/1,4-dioxane-d 8 1:1): (a) before irradiation, and after irradiation for (b) 15 min, (c) 30 min, (d) 60 min, and (e) 180 min. 6
7 Figure S6. 1 H NMR observation of the self-assembly from ligand 2a after heating at 80ºC without UV irradiation (500 MHz, D 2 O/1,4-dioxane-d 8 1:1): (a) before heating, and after heating for (b) 4 h, (c) 1 d, (d) 8 d, and (e) 36 d. 7
8 Figure S7. Frontier energy level scheme and some related molecular orbitals for [(en)pt(4a)] 4 8+, as calculated using DFT. 8
9 Figure S8. Frontier energy level scheme and some related molecular orbitals for [(en)pt(4b)] 3 6+, as calculated using DFT. 9
10 Figure S9. Frontier energy level scheme and some related molecular orbitals for [(en)pt(4c)] 6+ 3, as calculated using DFT. 10
11 Figure S10. Frontier energy level scheme and some related molecular orbitals for [(en)pt(4d)] 3 6+, as calculated using DFT. 11
12 Table S1. Cartesian Coordinates of [(en)pt(4a)] 8+ 4 optimized using the B3LYP level of the theory with the LANL2DZ basis set for Pt, and 6-31G* for the other atoms, respectively. [(en)pt(4a)]4 8+ Symmetry C1; singlet state; HF = Coordinates (Angstroms) Coordinates (Angstroms) Atom X Y Z Atom X Y Z C H C C H N H C C C N C H H H C C H C C H H H C C C C H C C H C H H H Pt C N H N H H C H C N H C N C H H H H N C C H N C H C H H H C H H H H H Pt C N C C C H C H H N H H C H C C C H C H Pt N H H H H H H C N C H H H C H C N N H C H H C H C N H Pt H H N C H C H H H C H
13 Table S2. Cartesian Coordinates of [(en)pt(4b)] 6+ 3 optimized using the B3LYP level of the theory with the LANL2DZ basis set for Pt, and 6-31G* for the other atoms, respectively. [(en)pt(4b)]3 6+ Symmetry C1; singlet state; HF = Coordinates (Angstroms) Coordinates (Angstroms) Atom X Y Z Atom X Y Z Pt N N N N C C C C C C H H H H C C C C H H H H H H H H C C H H H H C C C C C C C C C C H H H H C C H H H H C C C C C C C C C C H H H H N N H H H H Pt Pt N N N N N N C C C C C C C C H H H H H H H H C C C C H H H H H H H H H H H H C C H H H H C C C C C C H H H H
14 Table S3. Cartesian Coordinates of [(en)pt(4c)] 6+ 3 optimized using the B3LYP level of the theory with the LANL2DZ basis set for Pt, and 6-31G* for the other atoms, respectively. [(en)pt(4c)]3 6+ Symmetry C1; singlet state; HF = Coordinates (Angstroms) Atom X Y Z Pt N N N N C C H H H H C C C C H H H H C H H C C H H C H H C H H C C C C C C C C C C C H C C H H C C H H N Coordinates (Angstroms) Atom X Y Z H H N H Pt Pt N N N N N N C C H H H H C C C C C C H H H H H H H H C H H C C H H C H H H H H H C H H C C C
15 Table S4. Cartesian Coordinates of [(en)pt(4d)] 6+ 3 optimized using the B3LYP level of the theory with the LANL2DZ basis set for Pt, and 6-31G* for the other atoms, respectively. [(en)pt(4d)]3 6+ Symmetry C1; singlet state; HF = Coordinates (Angstroms) Atom X Y Z Pt N N N N C C C C C C H H H H C C C C H H H H H H H H C C H H H H C C C C C C C C C C C C C C C C C C C C H H H H H H H Coordinates (Angstroms) Atom X Y Z H H H H H C C H H H H H H H H H H H H C C C C C C C C H H H H N N H H H H Pt Pt N N N N N N C C C C C C C C H H H H H H H Coordinates (Angstroms) Atom X Y Z H C C C C H H H H H H H H H H H H C C H H H H C C C C C C C C C C H H H H H H H H H H H H
16 Table S5. Cartesian Coordinates of 4b optimized using the B3LYP level of the theory with the 6-31G* for all atoms. 4b Symmetry C1; singlet state; HF =
17 Table S6. Cartesian Coordinates of 4d optimized using the B3LYP level of the theory with the 6-31G* for all atoms. 4d Symmetry C1; singlet state; HF =
18 Table S7. Crystal data and structure refinement for 5 (H 2 O) m. Identification code Empirical formula PtTriangle5 C66 H123 N18 O37.50 Pt3 Formula weight Temperature Wavelength Crystal system 80(2) K Å Triclinic Space group P-1 Unit cell dimensions a = (18) Å α= (2). b = (3) Å β= (2). c = (3) Å γ = (2). Volume (11) Å 3 Z 2 Density (calculated) Mg/m 3 Absorption coefficient mm -1 F(000) 2358 Crystal size 0.16 x 0.15 x 0.10 mm 3 Theta range for data collection 1.91 to Index ranges -18<=h<=18, -24<=k<=25, -25<=l<=25 Reflections collected Independent reflections [R(int) = ] Completeness to theta = % Absorption correction Semi-empirical Max. and min. transmission and Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters / 780 / 1391 Goodness-of-fit on F Final R indices [I>2sigma(I)] R1 = , wr2 = R indices (all data) R1 = , wr2 = Largest diff. peak and hole and e.å -3 18
19 Figure S11. ORTEP views (30% probability level) of 5 (H 2 O) m. Water molecules and nitrate anions are severely disordered. 19
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Supporting Information for A general synthetic route to [Cu(X)(NHC)] (NHC = N- heterocyclic carbene, X =Cl, Br, I) complexes Orlando Santoro, Alba Collado, Alexandra M. Z. Slawin, Steven P. Nolan and Catherine
Supporting information. An unusual bifunctional Tb-MOF for highly sensing of Ba 2+ ions and remarkable selectivities of CO 2 /N 2 and CO 2 /CH 4
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Supporting Information Wiley-VCH 27 69451 Weinheim, Germany Supplementary Figure 1. Synthetic results as detected by XRD (Cu-Kα). Simulation pattern of MCM-68 Relative Intensity / a.u. YNU-2P Conventional
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data reports 2-(4-Methylphenyl)-2-oxoethyl 3,4-dimethoxybenzoate Structure description Synthesis and crystallization Refinement
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Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2014 Bis- and Tris(pyrazolyl)borate/methane-Stabilized P III -Centered Cations Lianghu Gu, Gopinadhanpillai Gopakumar,