Electronic Supplementary Information for Dalton Transactions. Supplementary Data
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- Κασσιέπεια Βιλαέτης
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1 Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2017 Electronic Supplementary Information for Dalton Transactions Supplementary Data Synthesis, spectroscopic, electrochemical and computational studies of rhenium(i) tricarbonyl complexes based on bidentate-coordinated 2,6- di(thiazol-2-yl)pyridine derivatives Tomasz Klemens a, Katarzyna Czerwińska a, Agata Szlapa-Kula b, Slawomir Kula b, Anna Świtlicka a, Sonia Kotowicz c, Mariola Siwy d, Katarzyna Bednarczyk c, Stanisław Krompiec b, Karolina Smolarek e, Sebastian Maćkowski e, Witold Danikiewicz f, Ewa Schab-Balcerzak c,d* and Barbara Machura a * a Department of Crystallography, Institute of Chemistry, University of Silesia, 9 th Szkolna St., Katowice, Poland b Department of Inorganic, Organometallic Chemistry and Catalysis, Institute of Chemistry, University of Silesia, 9 th Szkolna St., Katowice, Poland c Department of Polymer Chemistry, Institute of Chemistry, University of Silesia in Katowice, 9 th Szkolna St., Katowice, Poland d Centre of Polymer and Carbon Materials, Polish Academy of Sciences, 34 th M. Curie-Sklodowska St., Zabrze, Poland e Institute of Physics, Faculty of Physics, Astronomy and Informatics, Nicolaus Copernicus University, 5 th Grudziadzka St., Torun, Poland f Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, , Warsaw, Poland. 1
2 Tables: Table S1. Crystal data and structure refinement details of the rhenium(i) complexes. Table S2. The selected experimental and calculated bond lengths [Å] and angles [ ] for the rhenium(i) complexes. Table S3. Short intra- and intermolecular contacts detected in the structures of complexes. rhenium(i) Table S4. The absorption maxima and molar extinction coefficient values for complexes 4, 5, 6, 8 and their terpyridine analogues. Table S5. The energies and characters of the selected spin-allowed electronic transitions for 1 calculated with the TDDFT/PBE1PBE method, together with assignment to the experimental absorption bands. Table S6. The energies and characters of the selected spin-allowed electronic transitions for 2 calculated with the TDDFT/PBE1PBE method, together with assignment to the experimental absorption bands. Table S7. The energies and characters of the selected spin-allowed electronic transitions for 3 calculated with the TDDFT/PBE1PBE method, together with assignment to the experimental absorption bands. Table S8. The energies and characters of the selected spin-allowed electronic transitions for 4 calculated with the TDDFT/PBE1PBE method, together with assignment to the experimental absorption bands. Table S9. The energies and characters of the selected spin-allowed electronic transitions for 5 calculated with the TDDFT/PBE1PBE method, together with assignment to the experimental absorption bands. Table S10. The energies and characters of the selected spin-allowed electronic transitions for 6 calculated with the TDDFT/PBE1PBE method, together with assignment to the experimental absorption bands. Table S11. The energies and characters of the selected spin-allowed electronic transitions for 7 calculated with the TDDFT/PBE1PBE method, together with assignment to the experimental absorption bands. Table S12. The energies and characters of the selected spin-allowed electronic transitions for 8 calculated with the TDDFT/PBE1PBE method, together with assignment to the experimental absorption bands. Table S13. The energies and characters of the selected spin-allowed electronic transitions for 9 calculated with the TDDFT/PBE1PBE method, together with assignment to the experimental absorption bands. Table S14. The emission maxima for complexes 4, 5, 6, 8 and their terpyridine analogues. Figures: Figure S1. Representative IR spectra of complexes 2 and 5. Figure S2. Representative 1 H NMR (a) and 13 C NMR (b) spectra of complex 9. Figure S3. A view of the crystal packing showing intermolecular stacking interactions for tricarbonyl rhenium(i) complexes. Figure S4. Cyclic voltammograms of the rhenium(i) complexes. Figure S5. Absorption spectra of the rhenium(i) complexes in chloroform and acetonitrile solutions. 2
3 Figure S6. Experimental and theoretical absorption spectra of 1-9 complexes in acetonitrile solution. Figure S7. HOMO-5 to HOMO molecular orbitals of 1-9 complexes. Figure S8. LUMO to LUMO+5 molecular orbitals of 1-9 complexes. Figure S9. Isodensity surface electron spin density for the complexes 1 9 at their T 1 state geometry. Blue and green colours show regions of positive and negative spin density values, respectively. Figure S10. Isodensity surface plots of the HSOMO and LSOMO for the complexes 1 9 at their T 1 TDDFT state geometry. Blue and grey colours show regions of positive and negative spin density values, respectively. Figure S11. Luminescent properties of 1-9 complexes in solid state, low temperature glass matrix (EtOH:MeOH, 4:1 v/v), acetonitrile and chloroform solutions. Figure S12. PL spectra of [ReCl(CO) 3 (R n -dtpy)] complexes as film registered under various excitation wavelength ( ex ). 3
4 Table S1. Crystal data and structure refinement details of the rhenium(i) complexes Empirical formula C 19 H 10 ClN 4 O 3 S 2 Re C 18 H 9 ClN 3 O 3 S 3 Re C 22 H 11 ClN 3 O 3 S 4 Re C 20 H 11 ClN 3 O 4 S 2 Re C 19 H 12 ClN 4 O 3 S 2 Re C 28 H 20 ClN 4 O 4 ReS 2 Formula weight Temperature [K] 298.0(2) 298.0(2) 298.0(2) 298.0(2) 298.0(2) 298.0(2) Wavelength [Å] Crystal system monoclinic orthorhombic monoclinic monoclinic monoclinic monoclinic Space group P2 1 /c Pbca I2/a P2 1 /n P2 1 /n P2 1 /n Unit cell dimensions [Å, ] a = (4) a = (3) a = (5) a = (11) a = (3) a = (6) b = (4) b = (6) b = (4) b = (12) b = (5) b = (8) c = (5) c = (6) c = (9) c = (12) c = (7) c = (6) = (3) = (3) = (11) = (3) = (4) Volume [Å 3 ] (12) (2) (3) (4) (14) (3) Z Density (calculated) [Mg/m 3 ] Absorption coefficient [mm ] F(000) Crystal size [mm] 0.09 x 0.09 x x 0.06 x x 0.06 x x 0.15 x x 0.07 x x 0.16 x 0.05 range for data collection 3.41 to to to to to to [ ] Index ranges -13 h k l h k l h k l h k l h k l h k l 16 Reflections collected Independent reflections 3522 (R int = 3486 (R int = ) 4323 (R int = ) 3823 (R int = ) 3686 (R int = ) 5159 (R int = ) ) Completeness to 2 =50º [%] Max. and min. transmission and and and and and and Data / restraints / 3522 / 0 / / 0 / / 0 / / 0 / / 0 / / 0 / 362 parameters Goodness-of-fit on F Final R indices [I>2 (I)] R 1 = wr 2 = R 1 = wr 2 = R 1 = wr 2 = R 1 = wr 2 = R 1 = wr 2 = R 1 = wr 2 = R indices (all data) R 1 = wr 2 = R 1 = wr 2 = R 1 = wr 2 = R 1 = wr 2 = R 1 = wr 2 = R 1 = wr 2 =
5 Largest diff. peak and and and and and and and hole[eå -3 ] CCDC numbers
6 Table S2. The selected experimental and calculated bond lengths [Å] and angles [ ] for the rhenium(i) complexes experimental calculated experimental calculated experimental calculated Bond lengths Re(1) C(1) 1.916(8) (6) (4) Re(1) C(2) 1.907(6) (6) (4) Re(1) C(3) 1.908(7) (6) (4) Re(1) N(1) 2.161(5) (4) (3) Re(1) N(2) 2.239(4) (4) (2) Re(1) Cl(1) (15) (13) (8) C(1) O(1) 1.162(8) (6) (4) C(2) O(2) 1.145(7) (6) (4) C(3) O(3) 1.134(7) (6) (4) Bond angles C(2) Re(1) C(1) 89.0(2) (2) (15) C(3) Re(1) C(1) 89.0(2) (2) (15) C(3) Re(1) C(2) 87.7(2) (2) (14) C(1) Re(1) N(1) (19) (18) (12) C(2) Re(1) N(1) 95.2(2) (19) (12) C(3) Re(1) N(1) 96.1(2) (18) (13) C(1) Re(1) N(2) (18) (18) (12) C(2) Re(1) N(2) 169.0(2) (18) (12) C(3) Re(1) N(2) 95.66(19) (2) (12) N(1) Re(1) N(2) 74.08(15) (14) (9) C(1) Re(1) Cl(1) 90.41(17) (16) (11) C(2) Re(1) Cl(1) 94.40(19) (16) (11) C(3) Re(1) Cl(1) (17) (18) (10) N(1) Re(1) Cl(1) 84.30(12) (11) (8) N(2) Re(1) Cl(1) 82.39(11) (10) (6) Bond lengths experimental calculated experimental calculated experimental calculated 6
7 Re(1) C(1) 1.900(7) (6) (9) Re(1) C(2) 1.927(9) (8) (9) Re(1) C(3) 1.909(9) (7) (9) Re(1) N(1) 2.166(5) (4) (6) Re(1) N(2) 2.234(6) (5) (5) Re(1) Cl(1) 2.485(2) (16) (19) C(1) O(1) 1.152(8) (7) (9) C(2) O(2) 1.105(10) (9) (10) C(3) O(3) 1.127(9) (8) (9) Bond angles C(2) Re(1) C(1) 88.1(3) (3) (4) C(3) Re(1) C(1) 88.9(3) (3) (3) C(3) Re(1) C(2) 88.9(3) (3) (4) C(1) Re(1) N(1) 175.6(3) (2) (3) C(2) Re(1) N(1) 95.1(3) (2) (3) C(3) Re(1) N(1) 94.3(3) (2) (3) C(1) Re(1) N(2) 101.7(3) (2) (3) C(2) Re(1) N(2) 169.2(3) (2) (3) C(3) Re(1) N(2) 95.7(3) (2) (3) N(1) Re(1) N(2) 74.9(2) (18) (19) C(1) Re(1) Cl(1) 90.5(2) (19) (2) C(2) Re(1) Cl(1) 94.7(3) (2) (3) C(3) Re(1) Cl(1) 176.3(2) (19) (2) N(1) Re(1) Cl(1) 86.15(15) (13) (14) N(2) Re(1) Cl(1) 80.85(14) (11) (14)
8 Table S3. Short intra- and intermolecular contacts detected in the structures of rhenium(i) complexes. D H A D H H A D A [Å] D H A [ ] 3 C(4) H(4) O(2)# (8) C(10) H(10) N(4) (7) C(14) H(14) N(4)# (8) C(16) H(16) Cl(1)# (6) C(8) H(8) Cl(1)# (5) C(10) H(10) S(3) (5) C(13) H(13) S(3)# (6) C(16) H(16) Cl(1)# (5) C(4) H(4) N(3)# (5) C(8) H(8) S(1) (3) C(10) H(10) S(3) (3) C(5) H(5) Cl(1)# (8) C(15) H(15) O(4) (10) C(15) H(15) Cl(1)# (7) C(16) H(16) O(1)# (9) C(8) H(8) S(1) (6) C(13) H(13) S(1)# (7) C(14) H(14) N(3)# (8) C(17) H(17) O(3)# (9) C(19) H(19B) Cl(1)# (7) C(19) H(19C) Cl(1)# (8) O(4) H(4O) S(1) (17) O(4) H(4P) N(3)# (17) C(8) H(8) S(1) (7) C(14) H(14) Cl(1)# (13) C(27) H(27B) O(1)# (11) Symmetry codes: #1: -x,1-y,-z, #2: 1-x,2-y,1-z, #3: 1-x,-1/2+y,1/2-z, #4: -1/2+x,1/2-y,2-z; #5: 1-x,1-y,2-z, #6: -1/2+x,1-y,z; #7: 1/2-x,-1/2+y,1/2- z; #8: 1-x,-y,1-z; #9: 1/2+x,1/2-y,1/2+z, #10: -1/2+x,1/2-y,-1/2+z, #11: 5/2-x,1/2+y,1/2-z; #12: 1/2+x,1/2-y,-1/2+z; #13: 1+x,y,z, #14: 3-x,-y,1-z; #15: 1-x,2-y,-z; #16: x,y,-1+z; 8
9 Table S4. The absorption maxima and molar extinction coefficient values for complexes 4, 5, 6, 8 and their terpyridine analogues. Complex Ligand (medium) /nm (ε/ dm 3 mol-1 cm -1 ) terpy MeCN (4400), (13200), (12700), (14900) 4 dtpy MeCN (5600), (18720), (13480), (10880) terpy CHCl (23800), (91300), (97100), (85700) dtpy CHCl (5000), (22300), (16200), (13000) terpy MeCN (19800), (14900), (16300), (23700) 5 dtpy MeCN (30320), (22000), (20080) terpy CHCl (74900), (57600), (69700) dtpy CHCl (24480), (19520), (19480) terpy MeCN (7800), (45300), (57600), (60900) 6 dtpy MeCN (5000), (16160), (12000) terpy CHCl (24700), (96000), (88500), (76200) dtpy CHCl (6440), (30520), (25160), (15920) terpy MeCN (22200), (21100), (31400), (28600), (37800) 8 dtpy MeCN (10960), (14400), (21120), (14640) terpy CHCl (34600), (42600), (71500), (77700) dtpy CHCl (11640), (15640), (21160), (16920) 9
10 Table S5. The energies and characters of the selected spin-allowed electronic transitions for 1 calculated with the TDDFT/PBE1PBE method, together with assignment to the experimental absorption bands. Experimental absorption ; nm (ε; M -1 cm -1 ) (1560) (3780) (4800) Major contribution (%) Calculated transitions Character E [ev] λ [nm] Oscillator strength H L (98%) * H-1 L (96%) H-2 L (97%) MLCT/LC H L+1 (98%) H-1 L+1 (96%) H-3 L (91%) LC/ILCT H-2 L+1 (96%) MLCT/LC/ILCT H-4 L (88%) LC H-8 L (57%), H-3 L+1 (19%), H-7 L (14%) H-3 L+1 (44%), H-8 L (22%), H-7 L (13%), H-6 L (12%) LLCT/LC/MLCT LC/ILCT LLCT/LC/ILCT/MLCT LC/ILCT LLCT/LC/MLCT LLCT/LC/ILCT/MLCT ILCT H-4 L+1 (79%) LC/ILCT H-2 L+2 (48%), MLCT/ILCT/LC (5540) H-10 L (19%), LC/ILCT/LLCT H-9 L (14%) LC/ILCT/LLCT * mixed MLCT/LLCT state Table S6. The energies and characters of the selected spin-allowed electronic transitions for 2 calculated with the TDDFT/PBE1PBE method, together with assignment to the experimental absorption bands. Experimental absorption ; nm (ε; M -1 cm -1 ) Major contribution (%) Calculated transitions Character E [ev] λ [nm] Oscillator strength H L (98%) (4800) H-1 L (97%) H-2 L (97%) MLCT/LC H L+1 (98%) H-1 L+1 (96%) (24240) H-3 L (90%) LC H-2 L+1 (96%) MLCT/LC/ILCT H-5 L (89%) LC/ILCT (36560) H-3 L+1 (83%) LC/ILCT H-4 L+1 (79%) LC/ILCT/LLCT H-3 L+2 (82%) LC/ILCT H-10 L+1(66%) LC/ILCT (31120) H-5 L+2 (23%), H-11 L+1 (15%), H-13 L (13%) LC/ILCT ILCT/LLCT/LC LC Table S7. The energies and characters of the selected spin-allowed electronic transitions for 3 calculated with the TDDFT/PBE1PBE method, together with assignment to the experimental absorption bands. Experimental absorption Calculated transitions 10
11 ; nm (ε; M -1 cm -1 ) (3000) (8960) (15000) (12960) (%) strength H L (98%) H-1 L (97%) H-2 L (96%) MLCT/LC H L+1 (98%) H-1 L+1 (94%) H-3 L (88%) LC H-2 L+1 (96%) MLCT/LC H-4 L (50%), ILCT/LC/LLCT H-5 L (40%) LC H-3 L+1 (71%) LC/ILCT H-4 L+1 (54%), H-5 L+1 (12%), H-1 L+4 (10%) H-2 L+2 (68%), H-1 L+5 (10%) ILCT/LC/LLCT LC MLCT/d-d/LLCT MLCT/LC/ILCT d-d/mlct/llct Table S8. The energies and characters of the selected spin-allowed electronic transitions for 4 calculated with the TDDFT/PBE1PBE method, together with assignment to the experimental absorption bands. Experimental absorption ; nm (ε; M -1 cm -1 ) Major contribution (%) Calculated transitions Character E [ev] λ [nm] Oscillator strength H L (98%) (5600) H-1 L (97%) H-2 L (96%) MLCT H L+1 (97%) H-1 L+1 (94%) (18720) H-3 L (85%) ILCT/LC H-4 L (76%) LC (13480) H-3 L+1 (84%) ILCT/LC H-6 L (86%) ILCT (10880) H-5 L+1 (83%) LC Table S9. The energies and characters of the selected spin-allowed electronic transitions for 5 calculated with the TDDFT/PBE1PBE method, together with assignment to the experimental absorption bands. Experimental absorption ; nm (ε; M -1 cm -1 ) Major contribution (%) Calculated transitions Character E [ev] λ [nm] Oscillator strength H-1 L (63%), H L (30%) ILCT/LC H L (58%), ILCT/LC (30320) H-1 L (34%) H-2 L (84%) H-3 L (94%) MLCT/LC/ILCT H L+1 (89%) ILCT/LC H-1 L+1 (90%) H-2 L+1 (94%) (22000) H-4 L (90%) LC/ILCT H L+2 (91%) ILCT/LC (20080) H-6 L+1 (31%), LC/ILCT
12 H-3 L+2 (25%), H L+3 (15%) H-4 L+2 (51%), H-9 L+1 (12%), H-3 L+4 (10%) MLCT/ILCT/LC ILCT/LC LC/ILCT LLCT/LC/ILCT/MLCT d-d/mlct/lc Table S10. The energies and characters of the selected spin-allowed electronic transitions for 6 calculated with the TDDFT/PBE1PBE method, together with assignment to the experimental absorption bands. Experimental absorption ; nm (ε; M -1 cm -1 ) (5000) (16160) (12000) Major contribution (%) Calculated transitions Character E [ev] λ [nm] Oscillator strength H L (98%) H-1 L (96%) H-2 L (89%) MLCT/LC H L+1 (97%) H-3 L (77%) ILCT/LC/MLCT H-4 L (78%) LC H-3 L+1 (86%) ILCT/LC/MLCT H-5 L+1 (84%) LC H-2 L+2 (49%), MLCT/LC H-2 L+4 (24%) d-d/lc H-4 L+2 (86%) LC Table S11. The energies and characters of the selected spin-allowed electronic transitions for 7 calculated with the TDDFT/PBE1PBE method, together with assignment to the experimental absorption bands. Experimental absorption ; nm (ε; M -1 cm -1 ) (22320) (27360) (23920) (19200) Major contribution (%) Calculated transitions Character E [ev] λ [nm] Oscillator strength H-1 L (66%), H L (29%) ILCT/MLCT H L (53%), ILCT/MLCT H-1 L (32%), H-2 L (13%) /ILCT H-2 L (75%), H L (15%) /ILCT ILCT/MLCT H-3 L (90%) MLCT/LC H L+1 (69%), ILCT/MLCT H-1 L+1 (23%) H-1 L+1 (71%), H L+1 (16%) ILCT/MLCT H-4 L (76%), LC/ILCT H-2 L+1 (15%) /ILCT H-2 L+1 (78%), /ILCT H-4 L (10%) LC/ILCT H-3 L+2 (77%) MLCT/LC/ILCT H-5 L+1 (75%) LC/ILCT Table S12. The energies and characters of the selected spin-allowed electronic transitions for 8 calculated with the TDDFT/PBE1PBE method, together with assignment to the experimental absorption bands. Experimental absorption Calculated transitions 12
13 ; nm (ε; M -1 cm -1 ) (10960) (14400) (21120) (14640) Major contribution Oscillator Character E [ev] λ [nm] (%) strength H L (50%), /ILCT H-1 L (46%) H-1 L (53%), H L (38%) /ILCT H-2 L (80%) /ILCT/LC H-3 L (90%) MLCT/LC H L+1 (77%), /ILCT H-1 L+1 (18%) H-1 L+1 (80%), H L+1 (15%) /ILCT H-4 L (70%), LC H-2 L+1 (22%) /ILCT/LC H-2 L+1 (74%), /ILCT/LC H-4 L (20%) LC H-7 L (54%), /LC H-4 L+1 (37%) LC H-8 L (59%), /LC H-4 L+1 (7%) LC H L+2 (41%), /ILCT H L+4 (21%) d-d/ilct/lc H-6 L+1 (75%) LC/ H-3 L+3 (28%), d-d/lc H-1 L+4 (12%), d-d/llct/lc H L+3 (8%), d-d/ilct/lc H-2 L+2 (7%), /ILCT/LC H-2 L+4 (7%) d-d/llct/ilct/lc Table S13. The energies and characters of the selected spin-allowed electronic transitions for 9 calculated with the TDDFT/PBE1PBE method, together with assignment to the experimental absorption bands. Experimental absorption ; nm (ε; M -1 cm -1 ) (15720) (22480) Major contribution (%) H-7 L (29%) (21600) H-2 L+2 (26%), H L+3 (12%), H-5 L+1 (9%) Calculated transitions Character E [ev] λ [nm] Oscillator strength H-1 L (54%), H L (40%) ILCT H L (49%), ILCT H-1 L (44%) H-2 L (53%), /ILCT H-3 L (35%) /ILCT H-4 L (95%) MLCT/LC/ILCT H-3 L (53%), H-2 L (33%) /ILCT /ILCT H L+1 (83%) ILCT H-5 L (82%) LC/ILCT/MLCT H L+2 (47%), LC/ILCT H-4 L+1 (17%), MLCT/LC/ILCT H-3 L+1 (16%), /ILCT H-2 L+1 (12%) /ILCT H-6 L (45%), ILCT/LC LC/ILCT/ /LC/ILCT ILCT/LC LC/ILCT/MLCT
14 262.3 (22040) (27720) (31400) (31200) H-5 L+1 (66%) LC/ILCT/MLCT H-2 L+2 (21%), /LC/ILCT H L+3 (11%), ILCT/LC H-9 L (7%), LLCT/LC/ILCT H-3 L+2 (7%), /LC/ILCT H-3 L+5 (7%), d-d/ilct/mlct H-1 L+5 (7%) d-d/ H L+5 (32%), H L+4 (15%), H L+6 (14%) H L+7 (36%), H-1 L+7 (12%), H-1 L+9 (6%) H-1 L+7 (22%), H L+7 (14%), H-1 L+6 (11%), H L+9 (9%) ILCT/LMCT ILCT/LMCT ILCT/LC ILCT/LC ILCT/LC ILCT/LC Table S14. The emission maxima for complexes 4, 5, 6, 8 and their terpyridine analogues. Complex Medium Ligand [nm] terpy 664 MeCN dtpy terpy 675 CHCl 3 dtpy MeCN terpy 516 dtpy 682, 739 CHCl 3 terpy 484 dtpy 691, 735 MeCN terpy 663 dtpy 720 CHCl 3 terpy 675 dtpy 731 MeCN terpy 646 dtpy 716 CHCl 3 terpy 656 dtpy
15 2 5 Figure S1. Representative IR spectra of complexes 2 and 5. 15
16 (a) Figure S2. Representative 1 H NMR (a) and 13 C NMR (b) spectra of complex 9. (b) 16
17 3 4 17
18 5 7 18
19 9 Figure S3. A view of the crystal packing showing intermolecular stacking interactions for tricarbonyl rhenium(i) complexes. 19
20 Figure S4. Cyclic voltammograms of the rhenium(i) complexes. (1) (2) (3) 20
21 (4) (5) (6) 21
22 (7) (8) (9) 22
23 Figure S5. Absorption spectra of the rhenium(i) complexes in chloroform and acetonitrile solutions. Complex ACN CHCl
24
25 9 25
26 Figure S6. Experimental and theoretical absorption spectra of 1-9 complexes in acetonitrile solution
27 27
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