A Facile Route to Rare Heterobimetallic Aluminum-Copper. and Aluminum-Zinc Selenide Clusters
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1 Supporting Information For A Facile Route to Rare Heterobimetallic Aluminum-Copper and Aluminum-Zinc Selenide Clusters Bin Li, Jiancheng Li, Rui Liu, Hongping Zhu*, and Herbert W. Roesky*, State Key Laboratory of Physical Chemistry of Solid Surfaces, National Engineering Laboratory for Green Chemical Productions of Alcohols-Ethers-Esters, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen , China Institut fu r Anorganische Chemie, Georg-August-Universita t, Tammannstraβe 4, 37077Go ttingen, Germany Content: S1. Experimental Section S2.X-ray Crystallographic Analysis of Complexes 2 and 3 S3. NMR Spectra of Complexes 2 and 3 S4. Spectra of NMR tube reactions S5. TG analysis of Complexes 2 and 3 S6. References
2 S1. Exerimental Section Syntheses were carried out under a dry argon or nitrogen atmosphere using Schlenk line and glovebox techniques. Solvents including toluene and n-hexane were dried by refluxing with sodium/potassium benzophenone under N 2 prior to use. The NMR ( 1 H, 13 C, 27 Al and 77 Se) spectra were recorded on Bruker Avance II 400 MHz spectrometer. The 27 Al chemical shift is recorded relative to the 1 H resonance of tetramethylsilane (TMS) as no suitable reference sample was found. S1 Melting points of compounds were measured in a sealed glass tube using the Büchi-540 instrument. Elemental analysis was performed with a Thermo Quest Italia SPA EA 1110 instrument. TGA/DTA analysis was carried out on HCT-2 microcomputer differential thermal analyzer. Commercial reagents were purchased from Aldrich, Acros, or Alfa-Aesar Chemical Co. and used as received. Compounds LAl(SeH) 2 S2 and (CuMes) 4 S3 were prepared according to literature methods. [LAl(SeCu) 2 ] 2 (2, L = HC(CMeN-2,6-iPr 2 C 6 H 3 ) 2 ) LAl(SeH) 2 (0.302 g, 0.5 mmol) and (MesCu) 4 (0.183 g, 0.25 mmol) were placed in a flask ( 100 ml) and then cold toluene ( 20 C, 15 ml) was added dropwise under stirring at 20 C. The mixture was left to warm to room temperature and stirred for additional 24 h. All volatiles were removed under vacuum then n-hexane (10 ml) was added. The insoluble solid was removed by filtration and the n-hexane filtrate was stored at room temperature. After one day, colorless crystals of 2 were obtained. Yield: (0.20 g, 55%). Mp: 185 o C (decomp.). 1 H NMR (400 MHz, C 6 D 6, 298K, ppm): δ = 1.06 (d, 3 J HH = 6.8 Hz, 24 H, CHMe 2 ), 1.55 (s, 12 H, β-me), 1.65 (d, 3 J HH = 6.8 Hz, 24 H, CHMe 2 ), 3.63 (sept, 3 J HH = 6.8 Hz, 8 H, CHMe 2 ), 4.87 (s, 2 H, γ-ch), 7.09 (br, 12 H, C 6 H 3 ). 13 C NMR (100 MHz, C 6 D 6, 298K, ppm): δ = 24.88, 25.29, 26.96, (CHMe 2, CMe), (γ-ch), , , (C 6 H 3 ), (CN). 27 Al NMR (104.2 MHz, C 6 D 6, 298K, ppm): δ = (ν 1/2 = 400 Hz). 77 Se NMR (76.29 MHz, C 6 D 6, 298K, ppm, SnMe 2 in C 6 D 6 ): δ = Anal. Calcd(%) for C 58 H 82 Al 2 N 4 Cu 4 Se 4 (M r = ): C, 47.74; H, 5.66; N, Found: C, 47.30; H, 5.51; N, [LAl(Se) 2 ] 2 Zn 3 Et 2 (3, L = HC(CMeN-2,6-iPr 2 C 6 H 3 ) 2 ) LAl(SeH) 2 (0.240 g, 0.4 mmol) was placed in a flask (100 ml) and toluene (15 ml) was added. Then the solution was cooled to 70 C to which a 1 M n-hexane solution of ZnEt 2 (0.6 ml, 0.6 mmol) was added dropwise while stirring. After keeping at this temperature for 30 min, the mixture was left to warm to room temperature over 4 h. The color of the reaction mixture changed from yellow to colorless. The mixture was stirred for additional 12 h. The insoluble parts were removed by filtration, and the resulting filtrate was evaporated to dryness. The residue was extracted with n-hexane (10 ml). The n-hexane extract was stored at 20 C for one day, giving colorless crystals of 3. Yield: (0.18 g, 60%). Mp: 225 C (decomp.). 1 H NMR (400 MHz, C 6 D 6, 298K, ppm): δ = 0.03 (q, 3 J HH = 8 Hz, 4 H, CH 2 CH 3 ), 1.05 (d, 3 J HH = 8 Hz, 24 H, CHMe 2 ), 1.24 (t, 3 J HH = 8 Hz, 6 H, CH 2 CH 3 ), 1.45 (s, 12 H, β-me), 1.54 (d, 3 J HH = 8 Hz, 24 H, CHMe 2 ), 3.58 (sept, 3 J HH = 8 Hz, 8 H, CHMe 2 ), 4.76 (s, 2 H, γ-ch), (br, 12 H, C 6 H 3 ). 13 C NMR (100 MHz, C 6 D 6, 298K, ppm): δ = 8.86, (CH 2 CH 3 ), 24.20, 25.12, 26.50, (CHMe 2, CMe), (γ-ch), , , (C 6 H 3 ),
3 (CN). 27 Al NMR (104.2 MHz, C 6 D 6, 298K, ppm): δ = (broad peak). 77 Se NMR (76.29 MHz, C 6 D 6, 298K, ppm, SnMe 2 in C 6 D 6 ): δ = Anal. Calcd(%) for C 62 H 92 Al 2 N 4 Se 4 Zn 3 (Mr = ): C, 51.03; H, 6.35; N, Found: C, 51.46; H, 6.43; N, S2. X-ray Crystallographic Analysis of 2 and 3 Crystallographic data for (2) n-hexane and toluene were collected on an Oxford Gemini S Ultra system (Mo-Kα radiation, λ = Å). Absorption corrections were applied using the spherical harmonics program (multi-scan type). All structures were solved by direct methods (SHELXS-96) S4 and refined against F 2 using SHELXL-97. S5 In general, the non-hydrogen atoms were located by difference Fourier synthesis and refined anisotropically, and hydrogen atoms were included using a riding model with U iso tied to the U iso of the parent atoms unless otherwise specified. In (2) n-hexane, two independent main molecules and two n-hexane solvent molecules were located, of which the latter two molecules were determined by a half moiety with the occupations of the respective 0.25 and 0.5. The solvent carbon atoms were refined isotropically due to low occupation value. In toluene, three toluene molecules were located. Two of them were disordered and treated by PART splitting mode method. The final refinements gave a 60.04% occupation for C(63)C(64)C(65)C(66)C(67)C(68)C(69) and then a 39.96% occupation for C(63A)C(64A)C(65A)C(66A)C(67A)C(68A)C(69A) and a 84.74% occupation for C(70)C(71)C(72)C(73)C(74)C(75)C(76) and then a 15.26% occupation for C(70A)C(71A)C(72A)C(73A)C(74A)C(75A)C(76A). The third toluene molecule was seriously disordered and only a half moiety was located, in which the hydrogen atoms were not able to be included. Table S1. Crystal data and structure refinement for complexes n-hexane and toluene (2) n-hexane toluene formula C H Al 4 Cu 4 N 8 Se 8 C H 108 Al 2 N 4 Se 4 Zn 3 fw crystsyst Triclinic Triclinic space group P 1 P 1 a/å (5) (6) b/å (7) (4) c/å (8) (8) α/deg (3) (3) β/deg (3) (3) γ/deg (3) (3) V/Å (4) (3) Z 2 2 ρ calcd /g cm μ/mm F(000)
4 crystal size/mm θ range/deg h h 15 index ranges 23 k h l h 31 collected data unique data (R int = ) (R int = ) completeness to θ (%) data/restraints/params 26212/4/ /1234/ 949 GOF on F final R indices [I > 2(I)] R 1 = wr 2 = R 1 = wr 2 = R indices (all data) R 1 = wr 2 = R 1 = wr 2 = Largest diff peak/hole (e Å -3 ) 1.056/ / R 1 = ( F o F c )/ F o, wr 2 = [ w(f o 2 F c 2 ) 2 / w(f o 2 )] 1/2, GOF = [ w(f o 2 F c 2 ) 2 /(N o N p )] 1/2. Figure S1. Al 2 Cu 4 Se 4 core structure of 2 with thermal ellipsoids at 50% probability level. The ligands (L) are omitted for clarity. Selected bond lengths /Å and angles / : Se(1)-Cu(1) (8), Se(1)-Cu(2) (8), Se(1)-Al(1) (14), Cu(1) Cu(2) (11), Cu(1) Cu(4) (9), Cu(2) Cu(3) (8), Cu(3) Cu(4) (10); Se(1)-Al(1)-Se(2) (6), Se(3)-Al(2)-Se(4) (6). [Another independent molecule: Se(5)-Cu(8) (8), Se(5)-Cu(5) (8), Se(5)-Al(3) (17), Cu(5) Cu(6) (10), Cu(5) Cu(8) (9), Cu(6) Cu(7) (9), Cu(7) Cu(8) (9); Se(6)-Al(3)-Se(5) (6), Se(7)-Al(4)-Se(8) (6)].
5 Figure S2. Four AlSe 3 Cu 2 chair-shaped rings in core of 2. Dihedral angels in different rings [/ ] (Plane 1: AlSe 2 ; Plane 2: Cu 2 Se 2 ; Plane 3: Cu 2 Se). Angels between Plane 1 and 2, Plane 2 and 3, Plane 1 and 3 in turn: A , 9.811, ; B , , ; C , , 5.718; D , , Figure S3. Al 2 Se 4 Zn 3 core structure of 3 with thermal ellipsoids at 50% probability level. The ligands (L) and ethyl groups are omitted for clarity. Selected bond lengths /Å and angles / :Zn(1)-Se(1)2.4647(4), Zn(1)-Se(3)2.4913(5), Zn(1)-Zn(3) (5), Zn(2)-C(32) 1.954(3), Zn(2)-Se(2) (4), Zn(2)-Se(3) (5), Zn(3)-Se(4) (4), Zn(3)-Se(2) (4), Zn(3)-Se(1) (4), Zn(3)-Al(1)
6 2.9441(9), Zn(3)-Se(3) (4), Zn(3)-Al(2) (8), Se(1)-Al(1) (8), Se(2)-Al(1) (9), Se(3)-Al(2) (8), Se(4)-Al(2) (8); Se(2)-Al(1)-Se(1) (3), Se(4)-Al(2)-Se(3) (3), Se(1)-Zn(1)-Se(3) (16), Se(2)-Zn(2)-Se(3) (16), Se(4)-Zn(3)-Se(2) (18), Se(4)-Zn(3)-Se(1) (18), Se(2)-Zn(3)-Se(1) (15), Se(4)-Zn(3)-Se(3) (14), Se(2)-Zn(3)-Se(3) (14), Se(1)-Zn(3)-Se(3) (14). S3. NMR Spectra for complex 2 and 3 Figure S4. 1 H NMR spectrum of 2 recorded in C 6 D 6 at 298K.
7 Figure S5. 13 C NMR spectrum of 2 recorded in C 6 D 6 at 298K. Figure S6. 27 Al NMR spectrum of 2 recorded in C 6 D 6 at 298K.
8 Figure S7. 77 Se NMR spectrum of 2 recorded in C 6 D 6 at 298K. Figure S8. 1 H NMR spectrum of 3 recorded in C 6 D 6 at 298K.
9 Figure S9. 13 C NMR spectrum of 3 recorded in C 6 D 6 at 298K. Figure S Al NMR spectrum of 3 recorded in C 6 D 6 at 298K.
10 Figure S Se NMR spectrum of 3 recorded in C 6 D 6 at 298K. S4. Spectra of NMR tube reactions
11 Figure S12. 1 H NMR spectra of reaction of LAl(SeH) 2 with ZnEt 2 (1M n-hexane solution) in 2:3 molar ratio in C 6 D 6 at room temperature (A: the presence of the whole spectra; B: the presence of the γ-ch resonances for clarity). Trace amount of unknown impurity (*) exists in the starting material LAl(SeH) 2 even after several times recrystallization (less than 5%). After mixing LAl(SeH) 2 and ZnEt 2, the reaction finished completely within 5 min at room temperature. Figure A displays the disappearance of SeH resonance at ppm, and Figure B shows the formation of 3 based on the γ-ch resonance at 4.76 ppm. No intermediate was observed at room temperature. S5. TG analysis of Complexes 2 and 3 Figure S13. TG spectra of 2 and 3. The measurement was carried out through
12 temperature ramping rate at 10 o C/min in N 2 flow rate of 10 ml/min. In the TG spectra, complexes 2 and 3 display similar decomposition processes. According to the final weight percent as 30.8% for 2 and 32.7% for 3, we predicted the formation of Cu 2 Se and ZnSe after decomposition, respectively. S6. References (S1) Harris, R. K.; Becker, E. D.; Cabral, S. M.; Cabral De Menezes, S. M.; Goodfellow, R.; Granger, P. Pure Appl. Chem.2001, 73, (S2) Cui, C.; Roesky, H. W.; Hao, H.; Schmidt, H.-G.; Noltemeyer, M., Angew. Chem., Int. Ed.2000,39, (S3) Eriksson, H.; Håkansson, M. Organometallics1997, 16, (S4) Sheldrick, G. M. ActaCrystallogr., Sect. A 1990, 46, (S5) Sheldrick, G. M. SHELXL-97, Program for Crystal Structure Refinement; University of Göttingen: Göttingen, Germany, 1997.
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