A gadolinium(iii) complex that shows room-temperature phosphorescence in the crystalline state
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1 Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information (ESI) Table of Contents A gadolinium(iii) complex that shows room-temperature phosphorescence in the crystalline state Hidetaka Nakai,* abc Kazuhiro Kitagawa, ac Juncheol Seo, a Takahiro Matsumoto abc and Seiji go* abc a Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, 744 Moto-oka, Nishi-ku, Fukuoka , Japan b Centre for Small Molecule Energy, Kyushu University, 744 Moto-oka, Nishi-ku, Fukuoka , Japan c International Institute for Carbon-Neutral Energy Research (WPI-I2CNER), Kyushu University, 744 Moto-oka, Nishi-ku, Fukuoka , Japan Experimental details General..... S 2 X-ray crystallography.. S 3 Synthesis of [{( MeMe Ar) 3 tacn}gd III (THF)] (1 Phe ).. S 4 References... S 5 Tables Table S1 Crystallographic data for 1 Phe and 1 Phe + 1-naphtohol.. S 6 Table S2 Continuous shape measures (CSM) values calculated for the Gd 3+ in 1 Phe. S 7 Figures Fig. S1 A Gd(III) complex 1 Pyr and photographs of 1 Pyr. S 8 Fig. S2 PXRD pattern for the microcrystalline powder of 1 Phe.. S 9 Fig. S3 CIE chromaticity diagram of 1 Phe and 1 Phe + 1-naphtohol.. S10 Fig. S4 Luminescence decay curve of 1 Phe in the crystalline state. S11 Fig. S5 Luminescence spectra of 1 Phe in the crystalline state. S11 Fig. S6 Photographs of 1 Phe + 1-naphtohol.. S12 Fig. S7 Luminescence spectra of 1 Phe + 1-naphtohol in the crystalline state.. S13 Fig. S8 Luminescence decay curve of 1 Phe + 1-naphtohol in the crystalline state... S13 Fig. S9 An RTEP drawing 1 Phe + 1-naphtohol (1-naphtohol /1 Phe = 0.5 mol%).. S14 Fig. S10 Luminescence spectrum of 1 Phe under Ar in THF. S15 Fig. S11 Luminescence decay curve of 1 Phe under Ar in THF.. S15 S1
2 Experimental details General: All experiments were performed under a dry nitrogen or argon atmosphere using standard Schlenk techniques or a glovebox. Gd(Tf) 3 was purchased from Aldrich. {( MeMe ArH) 3 tacn} = {(CH 2 (CH 3 ) 2 C 6 H 2 H) 3 C 6 H 12 N 3 } was prepared according to the literature procedures. 1 All other chemicals were obtained from commercial sources and used as received unless otherwise noted. UV-vis absorption spectra were measured in a JASC V-670 UV-visible-NIR Spectrophotometer (cell length = 10.0 mm). Powder X-ray diffraction (PXRD) patterns were measured using an X-ray diffractometer (Rigaku SmartLab) with Cu-Kα radiation generated at 40 kv and 30 ma {scan speed: 1 min -1 (2θ= 5 30 )}. Elemental analyses were performed using a Yanaco CHN-coder MT-5. Corrected luminescence and excitation spectra, luminescence lifetimes (> 20 µs) and luminescence quantum yields were measured using a Horiba Jobin Yvon FluoroMax-4P Spectrofluorometer. Luminescence lifetimes (< 20 µs) were measured using a Horiba Jobin Yvon DeltaFlex Spectrofluorometer equipped with a NanoLED (300 nm) and a TBX-850 detector ( nm) with a WG-320 filter. Low temperature (77 K) spectra were obtained using a quartz tube cell (1 mm inner diameter) placed in a quartz-walled Dewar flask filled with liquid nitrogen. Luminescence quantum yields were measured by the relative comparison method with quinine bisulfate in 0.5 M H 2 S 4 (Φ = 0.60) chosen for the standard (the error in the reported values is within ±10%). 2 The general equation used for determination of relative quantum yields is given as Q x /Q st = [A st (λ)/a x (λ)][i x /I st ][n 2 x /n 2 st ], where A is the absorbance at an excitation wavelength, I is the integrated luminescence intensity and n is the refractive index. The subscripts x and st represent the sample and standard, respectively. Luminescence quantum yields of the crystals were measured using a Quanta-phi integration sphere. All spectroscopic measurements were independently repeated at least three times. S2
3 X-ray crystallography: All measurements were made on a Rigaku/MSC Saturn CCD diffractometer with confocal monochromated Mo Kα radiation (λ = Å). Data were collected and processed using CrystalClear 4 software (Rigaku). The data were corrected for Lorentz and polarisation effects. Empirical absorption corrections were applied. The structures were solved by direct methods: SIR-92 5 and expanded using a Fourier technique. All calculations were performed using the CrystalStructure 6 crystallographic software package except for refinement, which was performed using SHELXL2014/6 7. All non-hydrogen atoms were refined anisotropically. Hydrogen atoms were refined using the riding model. Crystallographic data has been deposited with the Cambridge Crystallographic Data Centre (CCDC). CCDC reference number: (1 Phe ). S3
4 Synthesis [{( MeMe Ar) 3 tacn}gd III (THF)] (1 Gd ) 8 H N H N N H i) Gd(Tf) 3 ii) NEt 3 Acetone/THF N N Gd N {( MeMe ArH) 3 tacn} [{( MeMe Ar) 3 tacn}gd III (THF)] A mixture of {( MeMe ArH) 3 tacn} (54 mg, 0.10 mmol) and Gd(Tf) 3 (60 mg, 0.10 mmol) in acetone/thf (100/1, 10 ml) was stirred for 5 min at room temperature. To the mixture was added dropwise triethylamine (0.06 ml, 0.43 mmol). The resulting solution was stirred for 3 h at room temperature. The white precipitate (microcrystalline powder: <100 µm in long axis, Fig. S2) was isolated by filtration and washed with acetone. Yield: 44 mg (70%). UV-Vis (THF): λ max /nm (ε/m 1 cm 1 ) = 303 (15000). Anal. calcd. for [{( MeMe Ar) 3 tacn}gd III (THF)] (C 37 H 50 GdN 3 4 ): C, 58.62; H, 6.65; N, 5.54%. Found: C, 58.62; H, 6.61; N, 5.52%. S4
5 References 1 D. A. Moore, P. E. Fanwick and M. J. Welch, Inorg. Chem., 1989, 28, K. Suzuki, A. Kobayashi, S. Kaneko, K. Takehira, T. Yoshihara, H. Ishida, Y. Shiina, S. ishi and S. Tobita, Phys. Chem. Chem. Phys., 2009, 11, R. Battino, T. R. Rettich and T. Tominaga, J. Phys. Chem. Ref. Data, 1983, 12, CrystalClear: Data Collection and Processing Software, Rigaku Corporation ( ). Tokyo , Japan. 5 A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, J. Appl. Cryst., 1993, 26, CrystalStructure 4.1.1: Crystal Structure Analysis Package, Rigaku Corporation ( ). Tokyo , Japan. 7 G. M. Sheldrick, Acta. Crystallogr., Sect. A: Fundam. Crystallogr., 2008, A64, H. Nakai, T. Goto, K. Kitagawa, K. Nonaka, T. Matsumoto and S. go, Chem. Commun., 2014, 50, S5
6 Tables Table S1 Crystallographic data for 1 Phe and 1 Phe + 1-naphthol 1 Phe 1 Phe +1-naphthol 0.5 mm 0.5 mm Formula C 37 H 50 N 3 4 Gd C 37 H 50 N 3 4 Gd Fw Crystal system triclinic triclinic Space group P-1 (No. 2) P-1 (No. 2) a (Å) (11) (18) b (Å) (19) (3) c (Å) (17) (3) α (deg) (4) (8) β (deg) (5) (8) γ (deg) (5) (9) V (Å 3 ) (4) (6) Z 2 2 µ (cm -1 ) F(000) D calcd (g/cm 3 ) Temperature (K) Reflections collected Independent (R int = 0.035) (R int = 0.032) Data/parameters 7659/ /412 R 1 [I > 2σ(I)] wr 2 (all data) Goodness-of-fit Photographs of the crystals of 1 Phe and 1 Phe + 1-naphthol were taken with an lympus SZX7 microscope connected with a digital camera (Nikon digital sight DS-U1) connected with a Leica DMLP polarizing microscope. S6
7 Table S2 Continuous shape measures (CSM) values calculated for the Gd 3+ in 1 Phe HP 7 HPY 7 PBPY 7 CC 7 CTPR 7 JPBPY 7 JETPY 7 1 Phe HP-7 (D 7h ) Heptagon HPY-7 (C 6v ) Hexagonal pyramid PBPY-7 (D 5h ) Pentagonal bipyramid CC-7 (C 3v ) Monocapped octahedron (Capped octahedron) CTPR-7 (C 2v ) Monocapped trigonal prism (Capped trigonal prism) JPBPY-7 (D 5h ) Johnson pentagonal bipyramid (J13) JETPY-7 (C 3v ) Johnson elongated triangular pyramid (J7) S7
8 Figures (a) (b) N N Gd N 1 Pyr Fig. S1 A gadolinium(iii) complex 1 Pyr and photographs of 1 Pyr in the crystalline state taken with a digital single-lens reflex camera (Canon ES KISS X5) at room temperature under (a) Ar and room light, (b) Ar and dark (λ ex = 254 nm). S8
9 0.5 mm Intensity θ (deg) 30 Fig. S2 Powder X-ray diffraction (PXRD) pattern for the microcrystalline powder (<100 µm in long axis) of 1 Phe (black) and the simulated pattern for the crystal (>200 µm in long axis) of 1 Phe (red). Photograph of the microcrystalline powder of 1 Phe was taken with an lympus SZX7 microscope connected with a digital camera (Nikon digital sight DS-U1) connected with a Leica DMLP polarizing microscope. S9
10 1 Phe + 1-naphthol in the crystalline state (0.283, 0.367) 1 Phe in the crystalline state (0.206, 0.198) Fig. S3 CIE 1931 chromaticity diagram of 1 Phe in the crystalline state and 1 Phe + 1-naphtol in the crystalline state at room temperature under air (λ ex = 250 nm). S10
11 Intensity Time / ms Fig. S4 Luminescence decay curve (red) of 1 Phe under air in the crystalline state at room temperature. The decay was monitored at 436 nm (λ ex = 250 nm). Fitted by bi-exponential curve (black: τ 1 = 293 µs, amplitude A 1 = 0.810; τ 2 = 117 µs, amplitude A 1 = 0.190). Intensity Wavelength / nm Fig. S5 Corrected luminescence spectra of 1 Phe under air in the crystalline state at room temperature. (λ ex = 250 nm). The spectra were acquired with a delay time of 0 µs (black) and (b) 50 µs (red). S11
12 (a) 1 Phe + 1-naphthol 1 Phe + 1-naphthol 1 Phe + 1-naphthol in THF Powder Crystal (b) at room temperature under air atmosphere (c) at room temperature under Ar atmosphere Fig. S6 Photographs of 1 Phe + 1-naphtol (1-naphthol/1 Phe = 0.5 mol%) in THF, in the microcrystalline powder state and in the crystalline state taken with a digital single-lens reflex camera (Canon ES KISS X5) at room temperature under (a) air and room light, (b) air and dark (λ ex = 254 nm) and (c) Ar and dark (λ ex = 254 nm). S12
13 Intensity Wavelength / nm Fig. S7 Corrected luminescence spectra of 1 Phe + 1-naphtol (1-naphthol/1 Phe = 0.5 mol%) under air in the crystalline state at room temperature. (λ ex = 250 nm). The spectra were acquired with a delay time of 0 µs (black), 50 µs (red) and (b) 500 µs (blue). Intensity Time / ms Fig. S8 Luminescence decay curve (red) of 1 Phe + 1-naphtol (1-naphthol/1 Phe = 0.5 mol%) under air in the crystalline state at room temperature. The decay was monitored at 538 nm (λ ex = 250 nm). Fitted by single-exponential curve (black: τ = 1272 µs). S13
14 1 4 N2 N1 3 2 N3 Gd mm Fig. S9 An RTEP drawing of 1 Phe + 1-naphtol (1-naphthol/1 Phe = 0.5 mol%) with 50% probability ellipsoids. Hydrogen atoms are omitted for clarity. Selected bond lengths [Å] and angles [ ]: Gd1 N1 = 2.574(2), Gd1 N2 = 2.561(2), Gd1 N3 = 2.554(2), Gd1 1 =, (17), Gd1 2 = (17), Gd1 3 = (17), Gd1 4 = (19), 1 Gd1 4 = 80.23(7), 2 Gd1 4 = 81.57(6), 3 Gd1 4 = 75.37(7). Photographs of the crystals of 1 Phe + 1-naphthol was taken with a digital camera (Nikon digital sight DS-U1) connected with a Leica DMLP polarizing microscope. S14
15 Intensity Wavelength / nm Fig. S10 Corrected luminescence spectrum of 1 Phe under Ar in THF at room temperature (λ ex = 250 nm). Intensity Time / ms Fig. S11 Luminescence decay curve of 1 Phe under Ar (red) in THF at room temperature. The decay was monitored at 436 nm (λ ex = 250 nm). Fitted by single-exponential curve (black: τ = 70 µs). S15
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