Electronic supplementary information (ESI) Bodipy functionalized ortho-carborane dyads for low-energy photosensitization
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1 Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2014 Electronic supplementary information (ESI) Bodipy functionalized ortho-carborane dyads for low-energy photosensitization Guo Fan Jin, a Yang-Jin Cho, a Kyung-Ryang Wee, a Seong Ahn Hong, a Il-Hwan Suh, a Ho-Jin Son, a Jong-Dae Lee, *b Won-Sik Han, *c Dae Won Cho, *a and Sang Ook Kang *a a Department of Advanced Materials Chemistry, Korea University, Sejong , South Korea. b Department of Chemistry, Chosun University, Gwangju , South Korea. c Department of Chemistry, Seoul Women s University, Seoul , South Korea. Contents Table S1 Fluorescence maxima for compounds 1 6 in various solvents Table S2 Oxidation and Reduction Potentials of compounds, 1 6 Table S3 Crystal data and structure refinement for compound 6 Table S4 Important bond lengths (Å), angle ( ) and torsion angles ( ) for crystal 6 Table S5 Selected oscillator strength and calculated electronic transitions of complexes Fig. S1 Energy levels and isodensity plots for selected occupied and unoccupied molecular orbitals of the complexes Fig. S2 Absorption and excitation spectra of compounds 5 6 in CH 2 Cl 2 at room temperature Fig. S3 1 H-NMR spectrum of compound 5 Fig. S4 13 C-NMR spectrum of compound 5 Fig. S5 11 B-NMR spectrum of compound 5 Fig. S6 19 F-NMR spectrum of compound 5 Fig. S7 1 H-NMR spectrum of compound 6 Fig. S8 13 C-NMR spectrum of compound 6 Fig. S9 11 B-NMR spectrum of compound 6 Fig. S10 19 F-NMR spectrum of compound 6 Fig. S11 Simulated absorption spectra of references (1 and 2) and dyads (5 and 6) calculated by TD-DFT Fig. S12 SEC spectra of Bodipys (1, 2 and 3) and dyad (6) 1
2 Table S1. Fluorescence maxima for compounds 1-6 in various solvents Solvent Compounds acetonitrile (nm) methylene chloride (nm) tetrahydrofuran (nm) n-hexane (nm) Excitation wavelength is 380 nm. Table S2. Oxidation and Reduction Potentials of compounds, 1-6 Oxidation peaks (V) a Reduction peaks (V) a HOMO LUMO Compounds (ev) c (ev) c E b pa E b pc E ox E b pa E b pc E red , -1.70, -1.65, , -1.70, -1.60, a Potentials calibrated with an internal ferrocene redox reference (Fc + Fc) using 0.1 M tetrabutylammonium perchlorate electrolyte in CH 2 Cl 2. b E pa = anodic peak potentials. E pc = cathodic peak potentials. E ox = half-wave oxidation potential between anodic and cathodic peaks. E red = half-wave reduction potential between anodic and cathodic peaks. c HOMO (ev) = e(e ox + 4.8) and LUMO (ev) = e (E red + 4.8). 2
3 Table S3. Crystal data and structure refinement for compound 6 Identification code Empirical formula Formula weight Temperature Wavelength Crystal system, space group Unit cell dimensions Volume Z, D calc μ F(000) Crystal size θ range for data collection Limiting indices Reflections collected / unique Completeness to θ = Refinement method Data / restraints / parameters Goodness-of-fit on F 2 Final R indices [I>2σ(I)] R indices (all data) Largest diff. peak and hole k C 51 H 59 B 12 Cl 2 F 4 N (2) K Å Monoclinic, P2 1 /n a = (2) Å b = (3) Å, β = 1016(4)º c = (5) Å (17) Å 3 4, g/cm mm mm 1.61 to 28.41º 17 h 17, 22 k 22, 34 l / [R int = 439] 99.4 % Full-matrix least-squares on F / 0 / R 1 = 814, wr 2 = 338 R 1 = , wr 2 = and e.å 3 a R 1 = F o - F c (based on reflections with F o2 >2 F 2 ), b wr 2 = [ [w(f o2 -F c2 ) 2 ]/ [w(f o2 ) 2 ]] 1/2 ; w = 1/[ 2 (F o2 )+(95P) 2 ];, P = [max(f o2, 0)+2F c2 ]/3(also with F o2 >2 F 2 ) 3
4 Table S4. Important bond lengths [Å], angle [ ] and torsion angles[ ] for 6. Numbering is for below crystal. Atom1-Atom2 Distance A1-A2-A3 Angle A1-A2-A3-A4 Angle C(1)-C(13) 1.428(4) C(1)-B(3)-C(2) 59.4(2) C(13)-C(1)-C(2)-C(39) -3.0(4) C(1)-C(2) C(2)-C(39) C(13)-C(14) C(14)-C(15) 1.714(4) 1.504(4) 1.185(4) 1.435(4) C(1)-B(3)-B(9) C(2)-B(3)-B(9) C(1)-B(6)-C(2) C(13)-C(1)-C(2) C(39)-C(2)-C(1) 104.8(3) 105.8(2) 59.4(2) 116.7(2) 117.4(2) C(2)-C(1)-C(13)-C(14) C(1)-C(13)-C(14)-C(15) C(13)-C(14)-C(15)-C(16) C(14)-C(15)-C(16)-C(17) C(17)-C(18)-C(21)-C(30) -29(4) -18(8) 143(4) (3) 89.6(4) C(1)-C(2)-C(39)-C(40) (3) C(1)-C(2)-C(39)-C(44) 51.2(4) C(44)-C(39)-C(40)-C(41) -1.2(4) C(2)-C(39)-C(40)-C(41) 175.9(3) C(41)-C(42)-C(45)-C(46) -90.9(4) C(43)-C(42)-C(45)-C(46) 88.9(4) 4
5 Table S5. Selected oscillator strength ( and calculated electronic transitions of complexes. 1 No. Osc. Strength Symmetry Major contributors Singlet HOMO LUMO (89%), H-1 LUMO (12%) Singlet H-1 LUMO (88%), HOMO LUMO (12%) Singlet H-2 LUMO (99%) Singlet HOMO L+2 (99%) Singlet H-4 LUMO (100%) Singlet H-5 LUMO (89%) Singlet H-1 L+2 (99%) Singlet H-7 LUMO (64%), HOMO L+3 (32%) Singlet HOMO L+3 (48%), H-7 LUMO (35%) Singlet H-5 L+1 (95%) Singlet HOMO L+4 (79%) Singlet H-3 L+1 (50%), H-4 L+2 (37%) Singlet H-12 LUMO (48%), H-11 LUMO (34%) Singlet H-11 LUMO (48%), H-12 LUMO (36%), HOMO L+4 (10%) Singlet H-13 LUMO (94%) Singlet HOMO L+5 (69%), H-1 L+3 (28%) Singlet H-15 LUMO (79%) Singlet H-17 LUMO (85%) Singlet H-14 LUMO (87%) Singlet H-18->LUMO (78%) Singlet H-1 L+3 (36%), HOMO L+8 (18%), HOMO L+5 (15%), HOMO L+6 (15%) Singlet H-2 L+3 (76%), H-18 LUMO (10%) Singlet H-4 L+1 (40%), H-3 L+2 (38%) Singlet H-4 L+2 (45%), H-3 L+1 (27%) Singlet H-19 LUMO (76%), H-20 LUMO (15%) Singlet HOMO L+7 (60%), H-1 L+4 (23%) Singlet H-1 L+4 (60%), HOMO L+7 (32%) 5
6 2 No. Osc. Strength Symmetr y Major contributors Singlet HOMO LUMO (89%), H-1 LUMO (12%) Singlet H-1 LUMO (87%), HOMO LUMO (-13%) Singlet HOMO L+1 (99%) Singlet H-2 LUMO (99%) Singlet HOMO L+2 (99%) Singlet H-4 LUMO (100%) Singlet H-5 LUMO (83%) Singlet H-6 LUMO (95%) Singlet H-3 L+1 (74%) Singlet H-9 LUMO (82%), HOMO L+3 (-16%) Singlet HOMO L+3 (69%), H-9 LUMO (17%) Singlet HOMO L+4 (50%), HOMO L+5 (35%) Singlet HOMO L+4 (48%), HOMO L+5 (-30%), H-5 L+2 (-13%) Singlet H-4 L+1 (41%), H-3 L+2 (32%) Singlet H-5 L+2 (74%) Singlet H-6 L+2 (38%), H-14 LUMO (-36%), H-13 LUMO (15%) Singlet H-6 L+2 (60%), H-14 LUMO (26%) Singlet H-13 LUMO (63%), H-14 LUMO (19%), HOMO L+5 (-11%) Singlet H-7 L+1 (28%), H-4 L+2 (-27%), H-8 L+1 (21%), HOMO L+6 (-15%) Singlet H-16 LUMO (89%) Singlet HOMO L+7 (95%) Singlet H-7 L+1 (61%), H-8 L+1 (-23%), H-4 L+2 (12%) Singlet H-17 LUMO (78%) 6
7 3 No. Osc. Strength Symmetr y Major contributors Singlet H-1 LUMO (55%), H-1 L+1 (39%) Singlet H-1 L+1 (31%), HOMO LUMO (23%), HOMO L+1 (19%), H-1 LUMO (-14%) Singlet HOMO L+1 (31%), H-1 LUMO (23%), H-1 L+1 (-19%), HOMO LUMO (14%) Singlet HOMO L+2 (60%), H-1 L+2 (-34%) Singlet H-1 L+2 (59%), HOMO L+2 (33%) Singlet H-2 LUMO (98%) Singlet H-3 LUMO (42%), H-4 L+1 (-40%) Singlet H-4 LUMO (41%), H-3 L+1 (-39%) Singlet H-6 LUMO (50%), H-5 L+1 (48%) Singlet H-2 L+2 (90%) Singlet H-1 L+4 (29%), HOMO L+3 (29%), H-1 L+3 (-19%), HOMO L+4 (18%) Singlet H-4 L+2 (96%) Singlet H-6 L+2 (98%) Singlet H-9 LUMO (51%), H-8 L+1 (48%) Singlet H-7 L+1 (55%), H-11 L+1 (33%) Singlet H-10 LUMO (62%), H-11 L+1 (11%) Singlet H-12 L+1 (54%), H-10 LUMO (21%), H-7 L+1 (20%) 7
8 4 No. Osc. Strength ymmetry Major contributors Singlet H-1 LUMO (20%), HOMO LUMO (20%), HOMO L+1 (16%), H-1 L+1 (-15%), HOMO L+2 (-11%), H-1 L+2 (10%) Singlet H-1 LUMO (20%), HOMO LUMO (-19%), H-1 L+1 (-16%), HOMO L+1 (-15%), H-1 L+2 (12%), HOMO +2 (11%) Singlet H-1 L+2 (38%), HOMO L+2 (-36%) Singlet HOMO L+2 (37%), H-1 L+2 (36%) Singlet H-2 L+1 (95%) Singlet H-4 LUMO (22%), H-3 LUMO (-22%), H-3 L+1 (22%), H-4 L+1 (21%) Single H-4 L+1 (23%), H-3 LUMO (22%), H-4 LUMO (21%), H-3 L+1 (-21%) Singlet H-5 LUMO (49%), H-6 L+1 (-48%) Singlet H-2 L+2 (80%), H-7 L+3 (-10%) Singlet HOMO L+3 (74%), H-1 L+3 (22%) Singlet H-1 L+3 (74%), HOMO L+3 (-22%) Singlet H-7 LUMO (92%) Singlet H-3 L+2 (92%) Singlet H-4 L+2 (92%) Singlet H-1 L+4 (34%), HOMO L+5 (-33%), H-1 L+5 (-17%), HOMO L+4 (-16%) Singlet H-10 LUMO (44%), H-11 L+1 (43%) Singlet H-11 LUMO (44%), H-10 L+1 (43%) Singlet H-7 L+3 (54%), H-8 L+1 (18%), H-9 LUMO (-17%) 8
9 5 No. Osc. Strength Symmetry Major contributors Singlet H-1 LUMO (-44%), HOMO L+1 (47%) Singlet H-1 L+1 (46%), HOMO LUMO (-41%) Singlet H-2 L+1 (35%), H-3 LUMO (32%), H-1 L+2 (-22%) Singlet H-2 LUMO (35%), H-3 L+1 (31%), HOMO L+2 (21%) Singlet H-4 L+1 (52%), H-5 LUMO (-45%) Singlet H-4 LUMO (54%), H-5 L+1 (-42%) Singlet HOMO L+3 (88%) Singlet H-1 L+3 (89%) Singlet HOMO L+4 (41%), H-1 L+4 (-35%), HOMO L+5 (10%) Singlet H-1 L+4 (41%), HOMO L+4 (36%), H-1 L+5 (-10%) Singlet HOMO L+5 (78%), H-1 L+4 (19%) Singlet H-6 LUMO (50%), H-7 L+1 (40%) Singlet H-6 L+1 (46%), H-7 LUMO (40%) Singlet H-2 L+2 (93%) Singlet H-3 L+2 (92%) Singlet H-7 L+1 (32%), H-6 LUMO (-28%), H-11 LUMO (10%), H-8 LUMO (-10%) Singlet H-7 LUMO (32%), H-6 L+1 (-29%), H-10 LUMO (11%), H-8 L+1 (-10%) Singlet H-10 L+1 (23%), H-7 L+1 (-19%), H-6 LUMO (18%), H-8 LUMO (-17%), H-11 LUMO (16%) Singlet H-2 L+3 (89%) Singlet HOMO L+6 (92%) Singlet H-9 L+1 (37%), H-8 LUMO (28%) Singlet H-4 L+3 (87%) Singlet H-5 L+3 (50%), H-8 L+1 (-21%), H-9 LUMO (-12%) Singlet H-5 L+3 (37%), H-8 L+1 (28%), H-9 LUMO (14%) Singlet H-10 L+1 (57%), H-11 LUMO (-20%), H-8 LUMO (18%) Singlet H-10 LUMO (46%), H-9 LUMO (-23%), H-11 L+1 (-14%) 9
10 6 No. Osc. Strength Symmetr y Major contributors Singlet HOMO L+2 (64%), HOMO L+1 (32%) Singlet H-1 LUMO (88%) Singlet HOMO L+1 (57%), HOMO L+2 (-31%), H-2 L+1 (-12%) Singlet H-1 L+2 (91%) Singlet H-2 LUMO (82%) Singlet H-4 LUMO (72%) Singlet H-2 L+1 (82%), HOMO L+1 (12%) Singlet H-5 LUMO (90%) Singlet H-3 L+1 (88%) Singlet HOMO L+3 (97%) Singlet H-1 L+3 (95%) Singlet HOMO L+5 (79%), HOMO L+4 (-18%) Singlet H-2 L+2 (97%) Singlet H-6 LUMO (99%) Singlet H-6 L+1 (96%) Singlet H-7 LUMO (82%) Singlet H-4 L+2 (94%) Singlet H-9 LUMO (92%) Singlet H-6 L+2 (80%) Singlet H-2 L+3 (93%) Singlet H-8 LUMO (97%) Singlet H-4 L+3 (90%) Singlet H-10 LUMO (95%) Singlet H-10 L+1 (91%) Singlet H-7 L+1 (94%) Singlet H-5 L+3 (80%) Singlet H-12 L+2 (38%), H-5 L+3 (-17%), H-7 L+2 (11%) 10
11 Fig. S1 Energy levels and isodensity plots for selected occupied and unoccupied molecular orbitals of the complexes. 11
12 Compound 1 Compound Absorption spectrum Excitation spectrum 1.0 Absorption spectrum Excitation spectrum Normalized Normalized Compound 3 Compound Absorption spectrum Excitation spectrum 1.0 Absorption spectrum Excitation spectrum Normalized Normalized Compound 5 Compound Absorption spectrum Excitation spectrum 1.0 Absorption spectrum Excitation spectrum Normalized Normalized Fig. S2 Absorption (black lines) and excitation (red lines) spectra of 1 6 in CH 2 Cl 2 at room temperature. 12
13 Fig. S3 1 H-NMR spectrum of compound 5. Fig. S4 13 C-NMR spectrum of compound 5. 13
14 Fig. S5 11 B{ 1 H}-NMR spectrum of compound 5. Fig. S6 19 F-NMR spectrum of compound 5. 14
15 Fig. S7 1 H-NMR spectrum of compound 6. Fig. S8 13 C-NMR spectrum of compound 6. 15
16 Fig. S9 11 B{ 1 H}-NMR spectrum of compound 6. Fig. S10 19 F-NMR spectrum of compound 6. 16
17 Absorbance Oscillation Strength Absorbance Oscillation Strength Absorbance Oscillation Strength Absorbance Oscillation Strength Fig. S11 Simulated absorption spectra of references (1 and 2) and dyads (5 and 6) calculated by TD-DFT. 17
18 6 1-2,29 V V 4 2-2,29 V V 3 2 A A A ,29 V V A V V V V V V Fig. S12 Spectroelectrochemical spectra for 1, 2, 3 and 6 under various voltages. 18
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![Table S1 Selected bond lengths [Å] and angles [ ] for complexes 1 8. Complex 1. Complex 2. Complex 3. Complex 4. Complex 5.](/thumbs/65/53614116.jpg "Table S1 Selected bond lengths [Å] and angles [ ] for complexes 1 8. Complex 1. Complex 2. Complex 3. Complex 4. Complex 5.")
Table S1 Selected bond lengths [Å] and angles [ ] for complexes 1 8. Complex 1 Zn(1) O(1) 1.969(2) Zn(1) O(5) 1.989(3) Zn(1) O(6) 1.930(3) Zn(1) O(4) a 1.954(4) Zn(1) O(3) a 2.519(25) O(6) Zn(1) O(4) a
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