Charged bis-cyclometalated Iridium(III) Complexes with Carbene-Based Ancillary Ligands
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1 Supporting Information Charged bis-cyclometalated Iridium(III) Complexes with Carbene-Based Ancillary Ligands Filippo Monti, Florian Kessler, Manuel Delgado, Julien Frey, Federico Bazzanini, Gianluca Accorsi, Nicola Armaroli,*, Henk J. Bolink, Enrique Ortí,*, Rosario Scopelliti, Md. Khaja Nazeeruddin, Etienne Baranoff*, Istituto per la Sintesi Organica e la Fotoreattività, Consiglio Nazionale delle Ricerche, Via P. Gobetti 101, Bologna, Italy Instituto de Ciencia Molecular, Universidad de Valencia, Paterna, Spain Laboratory of Photonics and Interfaces, Institute of Chemical Sciences and Engineering, École Polytechnique Fédérale de Lausanne, CH-1015 Lausanne, Switzerland School of Chemistry, University of Birmingham, Edgbaston, Birmingham B15 2TT, UK nicola.armaroli@isof.cnr.it, enrique.orti@uv.es, e.baranoff@bham.ac.uk S1
2 1. X-ray single crystal structures Figure S1. Perspective views of 2a, 2b, 3b, 4b, 5a, and 5b, from top left to bottom right. S2
3 Table S1. Crystallographic data for 2a, 2b, 3b, 4b, 5a and 5b. empirical formula formula weight temperature, K wavelength (Å) crystal system space group unit cell dimensions a (Å) b (Å) c (Å) α (deg) β (deg) γ (deg) volume (Å 3 ) Z density, calcd (g/cm 3 ) absorption coefficient (mm -1 ) F(000) crystal size (mm 3 ) θ range (deg) reflections collected independent reflections refinement method data/restraints/parameters goodness-of-fit on F2 final R indices [I > 2σ(I)] R indices (all data) 2a (2 CH2Cl2) C43H43Cl4F6IrN5P (2) Monoclinic P21/n (15) (6) (18) (8) (12) x 0.31 x to [R(int) = ] Full-matrix least-squares on F / 0 / R1 = wr2 = R1 = wr2 = b C41H35F10IrN5P (2) Triclinic P (2) (2) (12) (9) (13) (15) (6) x 0.18 x to [R(int) = ] Full-matrix least-squares on F / 0 / R1 = wr2 = R1 = wr2 = b (CH2Cl2) C33H25Cl2F10IrN5P (2) K Monoclinic P21/c 9.738(2) (3) (2) (8) (11) x 0.17 x to [R(int) = ] Full-matrix least-squares on F / 0 / R1 = wr2 = R1 = wr2 = b (acetone) C34H27F10IrN5OP (2) Monoclinic P21/c (15) (3) (11) (11) (6) x 0.19 x to [R(int) = ] Full-matrix least-squares on F / 0 / R1 = wr2 = R1 = wr2 = b (CH2Cl2) C32H26Cl2F10IrN6P (2) Triclinic P (8) (6) (14) (6) (8) (6) (2) x 0.20 x to [R(int) = ] Full-matrix least-squares on F / 0 / R1 = wr2 = R1 = wr2 = a (1.5 CH2Cl2) C32.50H31Cl3F6IrN6P (2) Monoclinic P21/n (3) (15) (17) (11) (7) x 0.32 x to [R(int) = ] Full-matrix least-squares on F / 0 / R1 = wr2 = R1 = wr2 = S3
4 2. Photophysical properties Figure S2. Absorption spectra of 1-5a in CH 3 CN at 298 K. The T 1 absorption transitions are magnified in the inset. Figure S3. Absorption spectra of 1-5b in CH 2 Cl 2 at 298 K. The T 1 absorption transitions are magnified in the inset. Figure S4. Normalized emission spectra of 1-5a in CH 3 CN at room temperature (λ exc = 360 nm). S4
5 Figure S5. Normalized emission spectra of 1-5b in CH 2 Cl 2 at room temperature (λ exc = 360 nm). Figure S6. Normalized emission spectra of 1-5b in CH 3 CN at room temperature (λ exc = 360 nm). Figure S7. Normalized emission spectra of 1-5b in CH 3 CN at 77 K (λ exc = 360 nm). S5
6 Figure S8. Normalized emission spectra of 1-5a in PMMA 1% at room temperature (λ exc = 360 nm). Figure S9. Normalized emission spectra of 1-5b in PMMA 1% at room temperature (λ exc = 360 nm). Figure S10. Room temperature normalized emission spectra of 1-5b as neat films (λ exc = 360 nm). S6
7 3. Theoretical Calculations Table S2. Selected bond distances (Å) and bond angles (º) calculated at the B3LYP/(6-31G**+LANL2DZ) level in the presence of the solvent (acetonitrile) for complexes 1 5 in the singlet ground state (S 0 ) and in the lowest-energy triplet state (T 1 ). Distances S 0 T 1 Angles S 0 T 1 1a Ir N 1 (C) N 1 (C) Ir C Ir C C 3 Ir C Ir N C 2 Ir N 1 (C) Ir N N 3 Ir N Ir C C 2 Ir C Ir C C 3 Ir N 1 (C) C 2 Ir C b Ir N 1 (C) N 1 (C)-Ir-C Ir C C 3 -Ir-C Ir N C 2 -Ir-N 1 (C) Ir N N 3 -Ir-N Ir C C 2 -Ir-C Ir C C 3 -Ir-N 1 (C) C 2 -Ir-C a Ir N 1 (C) N 1 (C)-Ir-C Ir C C 3 -Ir-C Ir N C 2 -Ir-N 1 (C) Ir N N 3 -Ir-N Ir C C 2 -Ir-C Ir C C 3 -Ir-N 1 (C) C 2 -Ir-C b Ir N 1 (C) N 1 (C)-Ir-C Ir C C 3 -Ir-C Ir N C 2 -Ir-N 1 (C) Ir N N 3 -Ir-N Ir C C 2 -Ir-C Ir C C 3 -Ir-N 1 (C) C 2 -Ir-C a Ir N 1 (C) N 1 (C)-Ir-C Ir C C 3 -Ir-C Ir N C 2 -Ir-N 1 (C) Ir N N 3 -Ir-N Ir C C 2 -Ir-C Ir C C 3 -Ir-N 1 (C) S7
8 C 2 -Ir-C b Ir N 1 (C) N 1 (C)-Ir-C Ir C C 3 -Ir-C Ir N C 2 -Ir-N 1 (C) Ir N N 3 -Ir-N Ir C C 2 -Ir-C Ir C C 3 -Ir-N 1 (C) C 2 -Ir-C a Ir N 1 (C) N 1 (C)-Ir-C Ir C C 3 -Ir-C Ir N C 2 -Ir-N 1 (C) Ir N N 3 -Ir-N Ir C C 2 -Ir-C Ir C C 3 -Ir-N 1 (C) C 2 -Ir-C b Ir N 1 (C) N 1 (C)-Ir-C Ir C C 3 -Ir-C Ir N C 2 -Ir-N 1 (C) Ir N N 3 -Ir-N Ir C C 2 -Ir-C Ir C C 3 -Ir-N 1 (C) C 2 -Ir-C a Ir N 1 (C) N 1 (C)-Ir-C Ir C C 3 -Ir-C Ir N C 2 -Ir-N 1 (C) Ir N N 3 -Ir-N Ir C C 2 -Ir-C Ir C C 3 -Ir-N 1 (C) C 2 -Ir-C b Ir N 1 (C) N 1 (C)-Ir-C Ir C C 3 -Ir-C Ir N C 2 -Ir-N 1 (C) Ir N N 3 -Ir-N Ir C C 2 -Ir-C Ir C C 3 -Ir-N 1 (C) C 2 -Ir-C S8
9 Table S3. B3LYP/(6-31G**+LANL2DZ)-optimized molecular geometries (x,y,z coordinates in Å) calculated for complexes 1 5a,b in the singlet ground state (S 0 ) and in the T 1 and 3 MC triplet states. The 3 MC state was not localized for complexes 5a and 5b. Complex 1a S 0 T 1 3 MC x y z x y z x y z Ir N C C N C C C C H N N C C C C C C C C C C H H H H H H C C C C C C C C C C S9
10 C C H H H H H H H H H H C H H H C C C C C C H N H H H C H H H H H Complex 1b S 0 T 1 3 MC x y z x y z x y z Ir N C C N C S10
11 C C C H N N C C C C C C C C C C H H H H H H C C C C C C C C C C C C H H H H F F F F H H C S11
12 H H H C C C C C C H N H H H C H H H H H Complex 2a S 0 T 1 3 MC x y z x y z x y z Ir N C C N C C C C H N N C C C C C C C S12
13 C C C H H H H H H C C C C C C C C C C C C H H H H H H H H H H C H H H C C C C C C H N H H S13
14 H C H H H H C H H C H H C H H C H H C H H H Complex 2b S 0 T 1 3 MC x y z x y z x y z Ir N C C N C C C C H N N C C C C C S14
15 C C C C C H H H H H H C C C C C C C C C C C C H H H H F F F F H H C H H H C C C C C C H N S15
16 H H H C H H H H C H H C H H C H H C H H C H H H Complex 3a S 0 T 1 3 MC x y z x y z x y z Ir N C C N C C C C H N N C C C S16
17 C C C C C C C H H H H H H C C C C C C C C C C C C H H H H H H H H H H C H H H C C N C H H S17
18 H H H H H Complex 3b S 0 T 1 3 MC x y z x y z x y z Ir N C C N C C C C H N N C C C C C C C C C C H H H H H H C C C C C C S18
19 C C C C C C H H H H F F F F H H C H H H C C N C H H H H H H H Complex 4a S 0 T 1 3 MC x y z x y z x y z Ir N C C N C C C S19
20 C H N N C C C C C C C C C C H H H H H H C C C C C C C C C C C C H H H H H H H H H H C C N S20
21 C H H H H H H H H Complex 4b S 0 T 1 3 MC x y z x y z x y z Ir , , , N , , , C , , , C , , , N , , , C , , , C , , , C , , , C , , , H , , , N , , , N , , , C , , , C , , , C , , , C , , , C , , , C , , , C , , , C , , , C , , , C , , , H , , , H , , , H , , , H , , , H , , , H , , , C , , , S21
22 C , , , C , , , C , , , C , , , C , , , C , , , C , , , C , , , C , , , C , , , C , , , H , , , H , , , H , , , H , , , F , , , F , , , F , , , F , , , H , , , H , , , C , , , C , , , N , , , C , , , H , , , H , , , H , , , H , , , H , , , H , , , H , , , H , , , Complex 5a S 0 T 1 x y z x y z Ir N N N N S22
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