Hexagon Wreaths: Self-Assembly of Discrete Supramolecular Fractal Architectures Using Multitopic Terpyridine Ligands

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1 Hexagon Wreaths: Self-Assembly of Discrete Supramolecular Fractal Architectures Using Multitopic Terpyridine Ligands Ming Wang,, Chao Wang,, Xin-Qi Hao, Jingjing Liu, Xiaohong Li, Chenglong Xu, Alberto Lopez, Luyi Sun, Mao-Ping Song, Hai-Bo Yang, # and Xiaopeng Li, * Department of Chemistry and Biochemistry, Texas State University, San Marcos, TX 78666, United States College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou , P. R. China Department of Chemical & Biomolecular Engineering and Polymer Program, Institute of Materials Science, University of Connecticut, Storrs, CT 06269, United States College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou , China # Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, Shanghai , P. R. China Table of Contents 1. Experimental section.s Synthesis of the ligands and complexes..s ESI mass spectra data of hexagon wreaths...s Calibration of drift time scale......s19 5. Molecular modeling results...s Photophysical properties of ligands and complexes..s H NMR, 13 C NMR, 2D COSY NMR, 2D NOESY NMR and 2D HSQC NMR and variable-temperature 1 H NMR....S TEM and energy-minimized structures from molecular modeling S52 9. Reference.... S53 S1

2 1. Experimental Section General Procedures. Compound 1, 5, 9 and 11 were purchased from Aldrich, Matrix Scientific, Alfa Aesar and used without further purification. Compound 7 was synthesized according to the reported method. 1 Column chromatography was conducted using basic Al 2 O 3 (Brockman I, activity, 58 Å) or SiO 2 (VWR, um, 60Å) and the separated products were visualized by UV light. 1 H NMR and 13 C NMR spectra data were recorded on a Bruker Avance 400-MHz and 600-MHz NMR spectrometer in CDCl 3 and CD 3 CN with TMS standard. UV vis absorption (UV) spectra were recorded with a PerkinElmer Lambda35 UV/Vis Spectrometer. Photoluminescence (PL) spectra were obtained on a PerkinElmer LS50B Luminescence spectrometer. Transmission Electron Microscopy (TEM) was obtained on JEOL Electrospray ionization (ESI) mass spectra were recorded with a Waters Synapt G2 tandem mass spectrometer, using solutions of 0.01mg sample in 1 ml of CHCl 3 /CH 3 OH (1:3, v/v) for ligand or 0.5 mg in 1 ml of MeCN/MeOH (3:1, v/v) for complex. TWIM MS. The TWIM MS experiments were performed under the following conditions: ESI capillary voltage, 3kV; sample cone voltage, 30 V; extraction cone voltage, 3.5 V; source temperature 100 ºC; desolvation temperature, 100 ºC; cone gas flow, 10 L/h; desolvation gas flow, 700 L/h (N 2 ); source gas control, 0 ml/min; trap gas control, 2 ml/min; Helium cell gas control, 100 ml/min; ion mobility (IM) cell gas control, 30 ml/min; sample flow rate, 5 μl/min; IM traveling wave height, 25 V; and IM traveling wave velocity, 1000 m/s. Q was set in rf-only mode to transmit all ions produced by ESI into the triwave region for the acquisition of TWIM MS data. S2

3 Collision cross-section calibration. The calibration procedure of Scrivens et al 2 was used to convert the drift time scale of the TWIM MS experiments to a collision cross-section (CCS) scale via the calibration curve was constructed by plotting the corrected CCSs of the molecular ions of cytochrome C (horse heart) 3 against the corrected drift times of the corresponding molecular ions measured in TWIM MS experiments at the same traveling wave velocity, traveling wave height, and ion mobility gas flow settings viz., 1000m/s, 25 V, and 30 ml/min, respectively. Molecular modeling. Energy minimization of the macrocycles was conducted with Materials Studio version 4.2, using the Anneal and Geometry Optimization tasks in the Forcite module (Accelrys Software, Inc.). All counterions are omitted. An initially energy-minimized structure was subjected to 70 annealing cycles with initial and mid-cycle temperatures of 50 K and 1500 K, respectively, twenty heating ramps per cycle, one thousand dynamics steps per ramp, and one dynamics step per femtosecond. A constant volume/constant energy (NVE) ensemble was used and the geometry was optimized after each cycle. Geometry optimization used a universal force field with atom-based summation and cubic spline truncation for both the electrostatic and van der Waals parameters. 70 energy-minimized structures were selected for the calculation of theoretical collision cross-sections using MOBCAL programs. TEM. The sample was dissolved in CH 3 CN at a concentration of 10-6 M. The solutions were drop cast on to a carbon-coated Cu grid and extra solution was absorbed by filter paper to avoid aggregation. The TEM images of the drop cast samples were taken with a JEOL 2010 transmission electron microscope. S3

4 2. Synthesis of the ligands and complexes 2-Hexyloxyl-5-bromobenzaldehyde (2). A mixture of 2-hydroxyl-5-bromo benzaldehyde (5.0 g, 25.0 mmol), 1-bromohexane (4.5 g, 27.5 mmol), K 2 CO 3 (6.9 g, 50.0 mmol) and DMF (25 ml) was heated at 110 C overnight. The mixture was cooled to room temperature. After DMF was removed under reduced pressure, the crude product was purified by a silica gel column chromatography. Compound 2 was obtained as light yellow oil with a yield of 92%. 1 H NMR (CDCl 3, 400 MHz, ppm): 1 H NMR (400 MHz, Chloroform-d) δ (d, J = 0.4 Hz, 1H, Ph-H D ), 7.92 (d, J = 2.8 Hz, 1H, Ph-H A ), 7.60 (ddd, J = 8.9, 2.6, 0.4 Hz, 1H, Ph-H B ), 6.89 (d, J = 8.9 Hz, 1H, Ph-H C ), 4.07 (t, J = 6.4 Hz, 2H, Alkyl-H E ), (m, 2H, Alkyl-H F ), (m, 2H, Alkyl-H G ), (m, 4H, Alkyl-H H and Alkyl-H I ), (t, J = 6.3 Hz, 3H, Alkyl-H J ). 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , 69.00, 31.45, 28.93, 25.65, 22.53, (hexyloxy)-5-((trimethylsilyl)ethynyl)benzaldehyde (3) : A solution of 2-Hexyloxyl-5-bromobenzaldehyde (4.7 g, 16.5 mmol), ethynyltrimethylsilane (3.2 g, 33.1 S4

5 mmol), palladium(ii) acetate (180 mg) and tri-phenylphosphine (360 mg) in anhydrous triethylamine (30 ml) was rapidly heated to 80 ºC under argon. After 30 h, the solvent was removed under reduced pressure and the residue was purified by column chromatography on SiO 2 with hexane: ethyl acetate (20:1) as eluent to afford compound 3 in 86% yield as an oil. 1 H NMR (400 MHz, Chloroform-d) δ (d, J = 0.4 Hz, 1H, Ph-H D ), 7.95 (d, J = 2.3 Hz, 1H, Ph-H A ), 7.62 (ddd, J = 8.6, 2.3, 0.5 Hz, 1H, Ph-H B ), 6.92 (d, J = 8.7 Hz, 1H, Ph-H C ), 4.10 (t, J = 6.5 Hz, 2H, Alkyl-H E ), (m, 2H, Alkyl-H F ), (m, 2H, Alkyl-H G ), (m, 4H, Alkyl-H H and Alkyl-H I ), (t, J = 6.4 Hz, 3H, Alkyl-H J ), 0.26 (s, 9H, Alkyl-H K ). 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , 93.74, 68.83, 31.47, 28.95, 25.66, 22.54, Compound 4. To a solution of NaOH powder (3.2 g, 80 mmol) in 70 ml EtOH, 2-(hexyloxy)-5-((trimethylsilyl)ethynyl)benzaldehyde (4.3 g, 15.0 mmol) and 2-acetylpyridine (4.0 g, 33.0 mmol) was added. After stirring at 25 ºC for 10 h, aqueous NH 3 H 2 O (50 ml) was added and the mixture was refluxed for 20 h. After cooling to room temperature, ethanol was removed under reduced pressure. The aqueous phase was extracted using DCM and the organic layer was washed with water three times. After the solvent was removed under reduced pressure, the residue was purified by column chromatography on S5

6 SiO 2 with DCM as eluent to afford compound 4 as white solid: 4.9 g (76%); 1 H NMR (400 MHz, Chloroform-d) δ (m, 2H, tpy-h 6,6'' ), 8.71 (s, 2H, tpy-h 3',5' ), 8.69 (dt, J = 8.0, 1.1 Hz, 2H, tpy-h 3,3'' ), 7.88 (ddd, J = 8.0, 7.5, 1.8 Hz, 2H, tpy-h 4,4'' ), 7.75 (d, J = 2.1 Hz, 1H, Ph-H A ), 7.52 (dd, J = 8.5, 2.2 Hz, 1H, Ph-H B ), 7.34 (ddd, J = 7.5, 4.8, 1.2 Hz, 2H, tpy-h 5,5'' ), 6.96 (d, J = 8.5 Hz, 1H, Ph-H C ), 4.04 (t, J = 6.2 Hz, 2H, Alkyl-H E ), 3.06 (s, 1H, H D ), (m, 2H, Alkyl-H F ), (m, 2H, Alkyl-H G ), (m, 4H, Alkyl-H H and Alkyl-H I ), (t, J = 6.4 Hz, 3H, Alkyl-H J ). 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , 83.39, 76.21, 68.66, 31.50, 29.04, 25.75, 22.34, Compound 10. To a flask containing Pd(PPh 3 ) 2 Cl 2 (56 mg, 0.08 mmol), CuI (7.6 mg, 0.04 mmol) and 1,3-dibromo-5-methoxybenzene (528 mg, 2.0 mmol) in 20 ml THF, 5 ml Et 3 N was added. After stirring at 50 ºC for 10 minutes, the solution of the compound 4 (433 mg, 1.0 mmol) in 10 ml THF was slowly added over 1 h. The mixture was heated at 50 ºC for 30 h. After removal of the volatile, the residue was purified by column chromatography on SiO 2 with chloroform as eluent to afford 10 in 75% yield as a yellow solid. 1 H NMR (400 MHz, Chloroform-d) δ 8.74 (s, 2H, tpy-h 3',5' ), 8.72 (ddd, J = 4.8, 1.8, 0.9 Hz, 2H, tpy-h 6,6'' ), 8.69 (dt, J = 8.0, 1.1 Hz, 2H, tpy-h 3,3'' ), (dt, J = 8.0, 1.8, 2H, tpy-h 4,4'' ), 7.80 (d, J = 2.1 S6

7 Hz, 1H, Ph-H A ), 7.54 (dd, J = 8.5, 2.2 Hz, 1H, Ph-H B ), 7.33 (ddd, J = 7.5, 4.8, 1.2 Hz, 2H, tpy-h 5,5'' ), (m, 1H, Ph-H D ), 7.04 (dd, J = 2.4, 1.8 Hz, 1H, Ph-H K ), 7.02 (dd, J = 2.4, 1.3 Hz, 1H, Ph-H L ), 6.97 (d, J = 8.6 Hz, 1H, Ph-H C ), 4.04 (t, J = 6.2 Hz, 2H, Alkyl-H E ), 3.81 (s, 3H, -OCH 3 ), (m, 2H, Alkyl-H F ), (m, 2H, Alkyl-H G ), (m, 4H, Alkyl-H H and Alkyl-H I ), 0.75 (t, J = 7.1 Hz, 3H, Alkyl-H J ). 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , , , 90.35, 87.12, 68.69, 55.57, 31.54, 29.08, 25.79, 22.37, Compound 8. To a solution of NaOH powder (4.8 g, 120 mmol) in100 ml EtOH, toluene 10 ml, 5-((trimethylsilyl)ethynyl)isophthalaldehyde (2 g, 8.7 mmol) and 2-acetylpyridine (5.26 g, 43.5 mmol) was added. After stirring at 25 ºC for 10 h, aqueous NH 3 H 2 O (70 ml) was added and the mixture was refluxed for 20 h. After cooling to room temperature, ethanol was removed under reduced pressure. The aqueous phase was extracted using DCM and the organic layer was washed with water three times. After the solvent was removed under reduced pressure, the residue was purified by column chromatography on SiO 2 with chloroform (1 % ethanol) as eluent to afford compound 8 as white solid: 2.8 g (56%); 1 H NMR (400 MHz, Chloroform-d) δ 8.83 (s, 4H, tpy-h 3',5' ), 8.77 (ddd, J = 4.8, 1.8, 0.9 Hz, 4H, S7

8 tpy-h 6,6'' ), 8.72 (dt, J = 8.0, 1.1 Hz, 4H, tpy-h 3,3'' ), 8.36 (t, J = 1.7 Hz, 1H, Ph-H A ), 8.14 (d, J = 1.7 Hz, 2H, Ph-H B ), (m, 4H, tpy-h 4,4'' ), 7.39 (ddd, J = 7.5, 4.8, 1.2 Hz, 4H, tpy-h 5,5'' ), 3.24 (s, 1H, H C ). 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , 82.91, Ligand LA. Under argon, a mixture of Pd(PPh 3 ) 2 Cl 2 (21 mg, 0.03 mmol), CuI (5.7 mg, 0.03 mmol), compound 10 (308 mg, 0.5 mmol) and compound 8 (282 mg, 0.5 mmol) in 20 ml DMSO and 5 ml Et 3 N was stirred at 80 ºC for 10 h. 100 ml water was added and used DCM to extract 3 time. After that, the organic layer was washed three times with water. DCM was removed and the residue was purified by column chromatography on SiO 2 with chloroform (2 % ethanol) as eluent to afford LA in 80% yield as a white solid. 1 H NMR (400 MHz, Chloroform-d) δ 8.85 (s, 4H, tpy-h 3',5' ), 8.77 (ddd, J = 4.8, 1.8, 0.9 Hz, 4H, tpy-h 6,6'' ), 8.75 (s, 2H, tpy-h a3',a5' ), (m, 6H, tpy-h a6,a6'' and tpy-h 3,3'' ), 8.68 (t, J = 0.6, 2H, tpy-h a3,a3'' ), 8.33 (d, J = 3.5, 1.7 Hz, 1H, Ph-H A ), 8.18 (d, J = 1.7 Hz, 2H, Ph-H B ), 7.91 (m, 6H, tpy-h a4,a4'' S8

9 and tpy-h 4,4'' ) 7.83 (d, J = 2.1 Hz, 1H, Ph-H F ), 7.59 (dd, J = 8.5, 2.1 Hz, 1H, Ph-H G ), 7.46 (t, J = 1.4 Hz, 1H, Ph-H C ), 7.38 (ddd, J = 7.5, 4.7, 1.2 Hz, 4H, tpy-h 5,5'' ), 7.34 (ddd, J = 7.5, 4.7, 1.2 Hz, 2H, tpy-h a5,a5'' ), 7.14 (ddd, J = 14.4, 2.5, 1.4 Hz, 2H, Ph-H D and Ph-H E ), 7.01 (d, J = 8.6 Hz, 1H, Ph-H H ), 4.08 (t, J = 6.2 Hz, 2H, Alkyl-H I ), 3.91 (d, J = 6.4 Hz, 3H, -OCH 3 ), (m, 2H, Alkyl-H J ), (m, 2H, Alkyl-H K ), (m, 4H, Alkyl-H L and Alkyl-H M ), 0.76 (t, J = 7.1 Hz, 3H, Alkyl-H N ). 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , 89.90, 89.62, 88.87, 87.79, 68.69, 55.54, 31.53, 29.08, 25.78, 22.36, ESI-HRMS (m/z): Calcd. for [C 74 H 55 N 9 O 2 +1H] 1+ and [C 74 H 55 N 9 O 2 +2H] 2+ : and Found: and S9

10 Complex [Zn 9 LA 6 ]. To a solution of ligand LA (6.0 mg, 5.4 μmol) in CHCl 3 (1 ml), a solution of Zn(NO 3 ) 2 6H 2 O (2.4 mg, 8.2 μmol) in MeOH (3 ml) was added; then the mixture was stirred at 50 ºC for 8 h. After cooling to room temperature, 200 mg NH 4 PF 6 was added and observed white precipitate, and used water to wash and obtained product (yield: 88%). 1 H NMR (400 MHz, Acetonitrile-d 3 ) δ 9.27 (m, 4H, tpy-h 3',5' and tpy-h b3',b5' ), 9.06 (s, 2H, tpy-h a3',a5' ), 8.97 (s, 1H, Ph-H A ), 8.87 (m, 4H tpy-h 3,3'' and tpy-h b3',b5' ), 8.71 (m, 2H, Ph-H B ), 8.68 (m, 2H, tpy-h a3,a3'' ), 8.27 (m, 2H, tpy-h 4,4'' ), 8.18 (m, 5H, tpy-h a4,a4'', tpy-h b4,b4'' and Ph-H F ), (m, 7H, tpy-h 6,6'', tpy-h a6,a6'', tpy-h b6,b6'' and Ph-H G ), 7.61 (m, 1H, Ph-H C ), 7.52 (m, 3H, tpy-h 5,5'' and Ph-H D ), (m, 6H, tpy-h a5,a5'', tpy-h b5,b5'', Ph-H E and Ph-H H ), 4.31 (s, 2H, Alkyl-H I ), 3.98 (s, 3H, -OCH 3 ), 1.80 (m, 2H, Alkyl-H J ), 1.49 (m, 2H, S10

11 Alkyl-H K ), 1.24 (m, 2H, Alkyl-H L ), 1.06 (m, 2H, Alkyl-H M ), 0.58 (m, 3H, Alkyl-H N ). 13 C NMR (100 MHz, CD 3 CN) δ , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , 99.92, 89.31, 87.86, 78.16, 69.13, 55.57, 29.94, 28.94, 25.77, 22.18, ESI MS (m/z): [M-8PF 6 ] 8+ (calcd m/z: ), [M-9PF 6 ] 9+ (calcd m/z: ), [M-10PF 6 ] 10+ (calcd m/z: 836.2), [M-11PF 6 ] 11+ (calcd m/z: 746.7), [M-12PF 6 ] 12+ (calcd m/z: 672.6) and [M-13PF 6 ] 13+ (calcd m/z: 609.7). Compound 12. To a flask containing Pd(PPh 3 ) 2 Cl 2 (35 mg, 0.05 mmol), CuI (5.7 mg, 0.03 mmol) and 1,3,5-triiodobenzene (456 mg, 1.0 mmol) in 20 ml THF, 8 ml Et 3 N was added. After stirring at 50 ºC for 10 minutes, the solution of the compound 8 (282 mg, 0.5 mmol) in 10 ml THF was slowly added over 1 h. The mixture was heated at 50 ºC for 28 h. After removal of the volatile, the residue was purified by column chromatography on SiO 2 with chloroform (1 % ethanol) as eluent to afford 6 in 70% yield as a white solid. 1 H NMR (400 MHz, Chloroform-d) δ 8.84 (s, 4H, tpy-h 3',5' ), 8.78 (ddd, J = 4.8, 1.8, 0.9 Hz, 4H, tpy-h 6,6'' ), S11

12 8.74 (dt, J = 7.9, 1.1 Hz, 4H, tpy-h 3,3'' ), 8.34 (t, J = 1.7 Hz, 1H, Ph-H A ), 8.15 (d, J = 1.7 Hz, 2H, Ph-H B ), 8.08 (t, J = 1.5 Hz, 1H, Ph-H D ), 7.97 (d, J = 1.6 Hz, 2H, Ph-H C ), 7.93 (ddd, J = 8.0, 7.5, 1.8 Hz, 4H, tpy-h 4,4'' ), 7.40 (ddd, J = 7.5, 4.8, 1.2 Hz, 4H, tpy-h 5,5'' ). 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , 94.04, 91.12, Ligand LB. Under argon, A mixture of Pd(PPh 3 ) 2 Cl 2 (21 mg, 0.03 mmol), CuI (5.7 mg, 0.03 mmol), compound 4 (433 mg, 1 mmol) and compound 12 (446 mg, 0.5 mmol) in 25 ml DMSO and 8 ml Et 3 N was stirred at 80 ºC for 16 h. 150 ml water was added and used DCM to extract 3 time. After that, the organic layer was washed with water three times. DCM was removed and the residue was purified by column chromatography on SiO 2 with chloroform (2 % ethanol) as eluent to afford LB in 71% yield as a white solid. 1 H NMR (400 MHz, Chloroform-d) δ 8.86 (s, 4H, tpy-h 3',5' ), (m, 8H, tpy-h 6,6' and tpy-h a3',a5' ), (m, 10H, tpy-h 3,3'', tpy-h a6,a6'' and tpy-h a3,a3'' ), 8.68 (t, J = 1.2 Hz, 2H, tpy-h a3,a3'' ), 8.35 (s, S12

13 1H, Ph-H A ), 8.18 (d, J = 1.7 Hz, 2H, Ph-H B ), (m, 8H, tpy-h a4,a4'' and tpy-h 4,4'' ), 7.83 (d, J = 2.1 Hz, 2H, Ph-H E ), 7.77 (d, J = 1.5 Hz, 2H, Ph-H C ), 7.73 (d, J = 1.5 Hz, 1H, Ph-H D ), (m, 2H, Ph-H F ), 7.36 (ddd, J = 7.5, 4.8, 1.2 Hz, 4H, tpy-h 5,5'' ), 7.32 (ddd, J = 7.5, 4.8, 1.2 Hz, 4H, tpy-h a5,a5'' ), 7.01 (d, J = 8.6 Hz, 2H, Ph-H G ), 4.07 (t, J = 6.2 Hz, 4H, Alkyl-H H ), (m, 4H, Alkyl-H I ), (m, 4H, Alkyl-H J ), (m, 8H, Alkyl-H K and Alkyl-H L ), 0.76 (t, J = 6.8 Hz, 6H, Alkyl-H M ). 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , 90.39, 89.64, 89.31, 87.22, 68.70, 31.52, 29.08, 25.77, 22.36, ESI-HRMS (m/z): Calcd. for [C 102 H 78 N 12 O 2 +1H] 1+ and [C 102 H 78 N 12 O 2 +2H] 2+ : and Found: and S13

14 Complex [Zn 12 LB 6 ]. To a solution of ligand LB (6.2 mg, 4.1 μmol) in CHCl 3 (1 ml), a solution of Zn(NO 3 ) 2 6H 2 O (2.5 mg, 8.2 μmol) in MeOH (3 ml) was added; then the mixture was stirred at 50 ºC for 8 h. After cooling to room temperature, 210 mg NH 4 PF 6 was added and observed white precipitate, and used water to wash and obtained product (yield: 91%). 1 H NMR (600 MHz, Acetonitrile-d 3 ) δ 9.22 (s, 4H, tpy-h 3',5' ), 9.10 (s, 4H, tpy-h a3',a5' ), 9.03 (m, 1H, Ph-H A ), 8.88 (m, 4H, tpy-h 3,3'' ), 8.70 (m, 6H, tpy-h a3,a3'' and Ph-H B ), 8.20 (m, 10H, tpy-h a4,a4'', tpy-h 4,4'' and Ph-H E ), 8.04 (s, 2H, Ph-H F ), 7.97 (m, 6H, tpy-h 6,6' and Ph-H G ), 7.89 S14

15 (m, 4H, tpy-h a6,a6'' ), 7.83 (m, 3H, Ph-H C and Ph-H D ), 7.43 (m, 8H, tpy-h 5,5'' and tpy-h a5,a5'' ), 4.34 (s, 4H, Alkyl-H H ), 1.91 (m, 4H, Alkyl-H I ), 1.51 (m, 4H, Alkyl-H J ), 1.29 (m, 4H, Alkyl-H K ), 1.06 (m, 4H, Alkyl-H L ), 0.62 (m, 6H, Alkyl-H M ). 13 C NMR (150 MHz, CD 3 CN) δ , , , , , , , , , , , , , , , , , , , , , , , 90.45, 89.70, 87.22, 69.16, 31.33, 28.95, 25.79, 22.22, ESI MS (m/z): [M-8PF 6 ] 8+ (calcd m/z: ), [M-9PF 6 ] 9+ (calcd m/z: ), [M-10PF 6 ] 10+ (calcd m/z: ), [M-11PF 6 ] 11+ (calcd m/z: ), [M-12PF 6 ] 12+ (calcd m/z: 962.3), [M-13PF 6 ] 13+ (calcd m/z: 876.9), [M-14PF 6 ] 14+ (calcd m/z: 804.0), [M-15PF 6 ] 15+ (calcd m/z: 740.9), [M-16PF 6 ] 16+ (calcd m/z: 685.2), [M-17PF 6 ] 17+ (calcd m/z: 636.5), [M-18PF 6 ] 18+ (calcd m/z: 593.2) and [M-19PF 6 ] 19+ (calcd m/z: 554.2). S15

16 3. ESI mass spectra data of [Zn 9 LA 6 ] and [Zn 12 LB 6 ] (PF 6 as counterion) [Zn 9 LA 6 ]: m/z m/z m/z m/z Figure S1. Measured (bottom) and calculated (top) isotope patterns for the different charge states observed from [Zn 9 LA 6 ] (PF 6 as counterion). [Zn 12 LB 6 ]: m/z 593 m/z S16

17 m/z m/z m/z 804 m/z m/z m/z m/z m/z S17

18 m/z m/z Figure S2. Measured (bottom) and calculated (top) isotope patterns for the different charge states observed from [Zn 12 LB 6 ] (PF 6 as counterion). S18

19 Corrected Collision Cross-Section 4. Calibration of drift time scale Corrected drift times (arrival times) against corrected published cross sections for the multiply charged ions arising from cytochrome C (horse heart). Drift times were measured at a traveling wave velocity of 1000 m/s and a traveling wave height of 25 V. This calibration plot was utilized to obtain the experimental collision cross sections (CCSs) listed in Table y = x 0.58 R 2 = Corrected Drift Time Figure S3. The calibration curve was constructed by plotting the corrected CCSs of the molecular ions of cytochrome C. S19

20 Collision Cross-Section (A 2 ) 5. Molecular modeling Complex [Zn 9 LA 6 ] Relative Energy (cal/mol) Figure S4. Plot of collision cross-section (CCS) vs. relative energy for 70 candidate structures of [Zn 9 LA 6 ] generated by annealing simulations. CCSs were calculated by the TJ method using the MOBCAL program. The average TJ CCS is ± 74.4 Å 2. S20

21 Collision Cross-Section (A 2 ) Relative Energy (cal/mol) Figure S5. Plot of collision cross-section (CCS) vs. relative energy for 70 candidate structures of [Zn 9 LA 6 ] generated by annealing simulations. CCSs were calculated by the PA method using the MOBCAL program. The average PA CCS is ± 67.4 Å 2. S21

22 Collision Cross-Section (A 2 ) Relative Energy (cal/mol) Figure S6. Plot of collision cross-section (CCS) vs. relative energy for 70 candidate structures of [Zn 9 LA 6 ] generated by annealing simulations. CCSs were calculated by the EHSS method using the MOBCAL program. The average EHSS CCS is ± 76.3 Å 2. S22

23 Collision Cross-Section (A 2 ) Complex [Zn 12 LB 6 ] Relative Energy (cal/mol) Figure S7. Plot of collision cross-section (CCS) vs. relative energy for 70 candidate structures of [Zn 12 LB 6 ] generated by annealing simulations. CCSs were calculated by the TJ method using the MOBCAL program. The average TJ CCS is ± 40.7 Å 2. S23

24 Collision Cross-Section (A 2 ) Relative Energy (cal/mol) Figure S8. Plot of collision cross-section (CCS) vs. relative energy for 70 candidate structures of [Zn 12 LB 6 ] generated by annealing simulations. CCSs were calculated by the PA method using the MOBCAL program. The average PA CCS is ± 25.1 Å 2. S24

25 Collision Cross-Section (A 2 ) Relative Energy (cal/mol) Figure S9. Plot of collision cross-section (CCS) vs. relative energy for 70 candidate structures of [Zn 12 LB 6 ] generated by annealing simulations. CCSs were calculated by the EHSS method using the MOBCAL program. The average EHSS CCS is ± 29.9 Å 2. S25

26 Normalized PL Normalized Absorbance 6. Photophysical properties of ligands and complexes 1.0 a 0.8 LA LB [Zn 9 LA 6 ] [Zn 12 LB 6 ] Wavelength (nm) 1.0 b 0.8 LA LB [Zn 9 LA 6 ] [Zn 12 LB 6 ] Wavelength (nm) Figure S10. UV (a) and PL (b) spectra of ligands in DCM and complexes in acetonitrile. S26

27 7. 1 H NMR, 13 C NMR, 2D COSY NMR, 2D NOESY NMR and 2D HSQC NMR Figure S11. 1 H NMR (400 MHz) spectrum of ligand LA. S27

28 Figure S C NMR (400 MHz) spectrum of ligand LA. S28

29 G H I J K L M N a3 a4 a5 a5 E a6 F a3 D C a3 a4 a6 a5 B b3 b4 3 b5 b5 b6 A 5 b3 3 b3 5 4 b4 b6 b5 Figure S13. 2D COSY NMR (400 MHz) spectrum of ligand LA. S29

30 6, ,3 a6,a6 a3,a A G H I J K L M N a3 a4 a5 a5 E a6 F a3 D C a3 a4 a6 a5 B b3 b4 3 b5 b5 b6 A 5 b3 3 b3 5 4 b4 b6 b5 B 4,4 5,5 a4,a4 G a5,a5 H Figure S14. 2D COSY NMR (400 MHz) spectrum of ligand LA (aromatic region). S30

31 I G H I J K L M N a3 a4 a5 a5 E a6 F a3 D C a3 a4 a6 a5 B b3 b4 3 b5 b5 b6 A 5 b3 3 b3 4 b4 b6 5 b5 J K L M N Figure S15. 2D COSY NMR (400 MHz) spectrum of ligand LA (aliphatic region). S31

32 Figure S16. 1 H NMR (400 MHz) spectrum of ligand LB. S32

33 Figure S C NMR (400 MHz) spectrum of ligand LB. S33

34 D 5 A 3 4 C B F G E a3 a3 a4 H I J a3 a4 a5 a5 a6 a5 a6 L M K Figure S18. 2D COSY NMR (400 MHz) spectrum of ligand LB. S34

35 6,6 3,3 a6,a6 a3,a3 A D 5 A 3 4 4,4 B C B a4,a4 E F G E a3 F a3 a4 H I J a3 a4 a5 a5 a6 a5 a6 5,5 L M K a5,a PF 6 - G Figure S19. 2D COSY NMR (400 MHz) spectrum of ligand LB (aromatic region). S35

36 H D 5 A 3 4 C B F G E a3 a3 a4 H I J a3 a4 a5 a5 a6 a5 a6 L M K I J K L M Figure S20. 2D COSY NMR (400 MHz) spectrum of ligand LB (aliphatic region). S36

37 Figure S21. 1 H NMR (400 MHz) spectrum of [Zn 9 LA 6 ]. S37

38 Figure S C NMR (400 MHz) spectrum of [Zn 9 LA 6 ]. S38

39 G H I J K L M N a3 a4 a5 a5 E a6 F a3 D C a3 a4 a6 a5 B b3 b4 3 b5 b5 b6 A 5 b3 3 b3 5 4 b4 b6 b PF 6 - Figure S23. 2D COSY NMR (400 MHz) spectrum of [Zn 9 LA 6 ]. S39

40 G H I J K L M N a3 a4 a5 a5 E a6 F a3 D C a3 a4 a6 a5 B b3 b4 3 b5 b5 b6 A 5 b3 3 b3 5 4 b4 b6 b PF 6-3,3 a3,a3 b3,b3 a4,a4 b4,b4 4,4 6,6 a6,a6 b6,b6 5,5 a5,a5 b5,b5 F G Figure S24. 2D COSY NMR (400 MHz) spectrum of [Zn 9 LA 6 ] (aromatic region). S40

41 G H I J K L M N a3 a4 a5 a5 E a6 F a3 D C a3 a4 a6 a5 B b3 b4 3 b5 b5 b6 A 5 b3 3 b3 5 4 b4 b6 b PF 6 - I J K L M N Figure S25. 2D COSY NMR (400 MHz) spectrum of [Zn 9 LA 6 ] (aliphatic region). S41

42 G H I J K L M N a3 a4 a5 a5 E a6 F a3 D C a3 a4 a6 4 a5 5 3 B b3 b4 3 6 b5 b5 b6 A 5 b b3 b4 b6 b5 3,3 a6,a6 3,5 b3,b3 b6,b6 a4,a4 b3,b5 a3,a3 b4,b4 6,6 a3,a5 5,5 A B 4,4 F PF 6 - a5,a5 b5,b5 Figure S26. 2D NOESY NMR (400 MHz) spectrum of [Zn 9 LA 6 ] (aromatic region). S42

43 28 ºC 40 ºC 50 ºC 60 ºC 70 ºC Figure S27. Variable-temperature (28 C - 70 C) 1 H NMR (400 MHz) signals of the aromatic protons for complex [Zn 9 LA 6 ] in CD 3 CN. S43

44 Figure S28. 1 H NMR (600 MHz) spectrum of [Zn 12 LB 6 ]. S44

45 Figure S C NMR (600 MHz) spectrum of [Zn 12 LB 6 ]. S45

46 D 5 A 3 4 C B F G E a3 a3 a4 H I J a3 a4 a5 a5 a6 a5 a6 L M K PF 6 - Figure S30. 2D COSY NMR (600 MHz) spectrum of [Zn 12 LB 6 ]. S46

47 3,3 5 6 a3,a D A C B F G E a3 a3 a4 H I J a3 a4 a5 a5 a6 a5 a6 L M K PF 6-4,4 a4,a4 5,5 6,6 a6,a6 a5,a5 Figure S31. 2D COSY NMR (600 MHz) spectrum of [Zn 12 LB 6 ] (aromatic region). S47

48 D 5 A 3 4 C B F G E a3 a3 a4 H I J a3 a4 a5 a5 a6 a5 a6 L M K PF 6 - H I J K L M Figure S32. 2D COSY NMR (600 MHz) spectrum of [Zn 12 LB 6 ] (aliphatic region). S48

49 5 6 a3,a5 a3,a3 3,5 3,3 B D 5 A 3 4 C B F G E a3 a3 a4 H I J a3 a4 a5 a5 a6 a5 a6 4,4 a4,a4 6,6 E a6,a6 L M K 5, PF 6 - a5,a5 Figure S33. 2D NOESY NMR (400 MHz) spectrum of [Zn 12 LB 6 ] (aromatic region). S49

50 CH 2 aliphatic area aromatic area Figure S34. 2D HSQC NMR (600 MHz) spectrum of [Zn 12 LB 6 ]. S50

51 28 ºC 40 ºC 50 ºC 60 ºC 70 ºC Figure S35. Variable-temperature (28 C - 70 C) 1 H NMR (400 MHz) signals of the aromatic protons for complex [Zn 12 LB 6 ] in CD 3 CN. S51

52 8. TEM and energy-minimized structures from molecular modeling 5 nm Figure S36. TEM image (left) and energy-minimized structure from molecular modeling (right) of complex [Zn 9 LA 6 ]. The long alkyl chains were omitted for clarity in the molecular modeling. Figure S37. The energy-minimized structures from molecular modeling of complexes [Zn 9 LA 6 ] (left) and [Zn 12 LB 6 ] (right). S52

53 10. References (1) Catala, L.; Turek, P.; Le Moigne, J.; De Cian, A.; Kyritsakas, N. Tetrahedron Lett. 2000, 41, (2) Thalassinos, K.; Grabenauer, M.; Slade, S. E.; Hilton, G. R.; Bowers, M. T.; Scrivens, J. H. Anal. Chem. 2008, 81, 248. (3) Fernandez-Lima, F. A.; Blase, R. C.; Russell, D. H. Int. J. Mass spectrom. 2010, 298, 111. S53

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