Room-temperature emissive liquid crystalline materials based on palladium(ii) imine derivatives containing the 2-phenylpyridine core
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1 Electronic Supplementary Information for: Room-temperature emissive liquid crystalline materials based on palladium(ii) imine derivatives containing the 2-phenylpyridine core Marin Micutz a, Monica Iliş a, Teodora Staicu a, Florea Dumitraşcu b, Iuliana Pasuk c, Yann Molard d, Thierry Roisnel d, Viorel Cîrcu a* a Dept. of Inorganic Chemistry, University of Bucharest, 23 Dumbrava Rosie st, sector 2, Bucharest , Romania, viorel_carcu@yahoo.com, viorel.circu@g.unibuc.ro b Centre for Organic Chemistry C. D. Nenitzescu, Romanian Academy, Spl. Independentei 202B, Bucharest , Romania c National Institute of Materials Physics, P.O. Box MG-7, Magurele, 07712, Romania d Sciences Chimiques de Rennes UMR 6226 CNRS Université de Rennes 1, Avenue du Général Leclerc 3042 Rennes Cedex, France Content: 1. Scheme 1. Preparation of N-benzoyl-N -aryl thiourea derivatives (BTU) p.2 2. Table 1. Crystallographic data for complexes. p.3 3. Table 2. Bond lengths (Å) and angles (º) for complexes 3, 4b and 9 p.4 4. Table 3. X-ray diffraction data for Pd(II) complexes (11 and 12) p.. Figure S1. Pictures of taken at room temperature, without irradiation (a) and of the same area irradiated within the nm range (b) p.6 6. Figure S2. POM textures shown by complex 11 at 140 o C (a) and complex 12 at 1 o C (b). Pictures of complex 12 taken at 30 C with no irradiation (c) and irradiated within the nm range (d) p.6 7. Figure S3. Powder X-ray diffractogram of complex 11 recorded at 30ºC before melting p.7 8. Figure S4. The emission spectrum of complex 3, (λ exc = 380 nm, Φ = 0.08, 1x -4 M in CH 2 Cl 2 solution) p.7 9. Figure S. DSC curve for 1b (first heating-cooling cycle (a) and second heating - cooling cycle (b)) p.8. Figure S6. DSC trace for complex p Figure S7. DSC trace for complex 11, first heating-cooling cycle (a) and second heating-cooling cycle (b) p Figure S8. DSC trace for complex 12 p Figure S9. The emission spectra of palladium(ii) complexes recorded in dichloromethane solution p. 14. Figure S. The solid-state emission spectra of 12 (λ exc =380 nm) p. 1. Figure S11. The solid-state emission of 11 before and after heating (λ exc =480 nm) p Figure S12. The solid-state emission of 12 before and after heating (λ exc =480 nm) p References p.11 1
2 (O)H R 3 R 3 H(O) R-Br R 2 HCl R 2 H(O) COOCH 3 K 2 CO 3 Butanone R 1 COOCH 3 EtOH R 1 COOH R 3 R 3 SOCl 2 R 2 KSCN R 2 CH 2 Cl 2 R 1 C Cl Acetone R 1 CONCS O R 3 H 2 N OC 8 H 17 Acetone R 2 R 1 H N H N 6: R 1 = R 3 = H, R 2 = 2-ethylhexyloxy 7: R 1 = R 2 = -OC 12 H 2, R 3 = H O S OC 8 H 17 8: R 1 = R 2 = R 3 = -OC 12 H 2 Scheme 1. Preparation of N-benzoyl-N -aryl thiourea derivatives (BTU) 1 2
3 Table 1. Crystallographic data for complexes. 3 4b 9 Empirical formula C 26 H 27 N 3 O 2 PtS C 29 H 38 Cl 4 N 2 O 2 PtS C 4 H 66 N 6 O 3 Pd 2 S 2 M T/K (2) (2) (2) λ/nm Å 0.773Å Å Crystal system monoclinic triclinic triclinic Space group P 2 1 /n P -1 P -1 a/ Å 1.741(3) 7.43(9).2638() b/ Å () 8.23() 14.47(14) c/ Å (3) (3) (16) α/ () (3) β/ 9.10() () (4) γ/ () 73.76(4) V/ Å (7) 187.1(3) (4) Z, Calculated density(g.cm -3 ) Absorption coefficient,µ/mm F(000) Crystal size/mm 0.34 x 0.21 x x 0.13 x x 0.16 x 0.1 Crystal color yellow yellow yellow θ range for data collection/ 2.91 to to to h_min, h_max -20, 20-9, 9-13, 13 k_min, k_max -, 9 -, -18, 18 l_min, l_max -2, 23-34, 34-19, 24 Reflections collected / unique / / / 1170 [R(int) a = ] [R(int) a = ] [R(int) a = ] Completeness to θ max Max. and min. transmission 0.66, , , Data / restraints / parameters 439 / 0 / / 0 / / 0 / 96 b Goodness-of-fit Final R indices [I>2σ] R1 c = R1 c = R1 c = wr2 d = wr2 d = wr2 d = R indices (all data) R1 c = R1 c = 0.0, R1 c = wr2 d = wr2 d = wr2 d = Largest diff. peak and hole/ 0.60 and and and e.å -3 a R int = F o 2 - < F o 2 > / [F o 2 ] b S = { [w(f o 2 - F c 2 ) 2 ] / (n - p)} 1/2 c R1 = F o - F c / F o d wr2 = { [w(f o 2 - F c 2 ) 2 ] / [w(f o 2 ) 2 ]} 1/2 w = 1 / [σ(f o 2 ) + ap 2 + bp] where P = [2F c 2 + MAX(F o 2, 0)] /3 3
4 Table 2. Bond lengths (Å) and angles (º) for complexes 3, 4b and 9 Complex 3 4b 9 M-C 1.980(3) (4) 2.09(4) M-O 2.080(2) (3) 2.070(3) M-N 2.037(2) 2.078(4) 2.069(3) 1.982(4) M-S 2.247(8) (13) 2.212(12) 2.247(13) Pt-Cl(1) (13) Pt-Cl(2) (13) C-M-N 80.9(11) (16) 81.28(16) C-M-S 94.93(9) (13) 93.(13) N-M-O 91.21(9) (12) 92.8(13) O-M-S 93.40(6) (9) 93.0(9) N-Pt-Cl (12) S-Pt-Cl () N-Pt-Cl (12) S-Pt-Cl () 4
5 Table 3. X-ray diffraction data for Pd(II) complexes (11 and 12) Compound T/( o C) d exp /Å Indexation d calc /Å Mesophase parameters d 36.2 Col h d a=41.8 Å d Z~1..30 d 22.4 S=113 Å d d d d h ch 3.6 h 0 d exp / Å Indexation d calc /Å Mesophase parameters d 32.9 Col h 19.1 d a = 38.0 Å 16. d Z~ d S h = 121Å 2.9 d h ch 3.6 h 0 The columnar lattice parameter was calculated with the following relationship a = d x 2/3 1/2, where the cross-section area was calculated as following: S = a 2 x3 1/2 /2.
6 (a) (b) Figure S1. Pictures of taken at room temperature, without irradiation (a) and of the same area irradiated within the nm range (b) (a) (b) (c) (d) Figure S2. POM textures shown by complex 11 at 140 oc (a) and complex 12 at 1 oc (b). Pictures of complex 12 taken at 30 C with no irradiation (c) and irradiated within the nm range (d) 6
7 Intensity/cps θ/ Figure S3. Powder X-ray diffractogram of complex 11 recorded at 30ºC before melting Intensity/arbitrary units λ/nm Figure S4. The emission spectrum of complex 3, (λ exc = 380 nm, Φ = 0.08, 1x -4 M in CH 2 Cl 2 solution) 7
8 2 20 (a) 2 20 (b) T/ C T/ C Figure S. DSC curve for 1b (first heating-cooling cycle (a) and second heating - cooling cycle (b)) T/ C Figure S6. DSC trace for complex 8
9 T g = 24 C T/ 0 C (a) Figure S7. DSC trace for complex 11, first heating-cooling cycle (a) and second heatingcooling cycle (b) (b) T/ C 1 T g = 21 C T/ C Figure S8. DSC trace for complex 12 9
10 Normalized intensity (λ ex =28 nm) 11 (λ ex =283 nm) 12 (λ ex =283 nm) λ/nm Figure S9. The emission spectra of palladium(ii) complexes recorded in dichloromethane solution Intensity/arbitrary units λ/nm Figure S. The solid-state emission spectra of 12 (λ exc =380 nm)
11 solid, before heating after heating Intensity/arbitrary units λ/nm Figure S11. The solid-state emission of 11 before and after heating (λ exc =480 nm) solid, before heating after heating Intensity/arbitrary units λ/nm Figure S12. The solid-state emission of 12 before and after heating (λ exc =480 nm) References: 1. M. Ilis, M. Bucos, F. Dumitrascu and V. Circu, J. Mol. Struct., 2011, 987, 1. 11
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