Supporting information. Random Structural Modification of a Low Band Gap BODIPY-Based Polymer
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1 Supporting information Random Structural Modification of a Low Band Gap BODIPY-Based Polymer Léo Bucher, a,b Shawkat M. Aly, a Nicolas Desbois, b Paul-Ludovic Karsenti, a Claude P. Gros, b * and Pierre D. Harvey a * a Département de Chimie, Université de Sherbrooke, 2500, Bd de l Université J1K 2R1 Sherbrooke, QC, Canada. Pierre.Harvey@USherbrooke.ca b Université de Bourgogne Franche-Comté, ICMUB (UMR CNRS 6302), 9, Avenue Alain Savary, BP 47870, Dijon Cedex, France. Claude.Gros@u-bourgogne.fr S1
2 FIGURES Characterization of 1 Figure S1: 1 H NMR spectrum of 1 Figure S2: 13 C NMR spectrum of 1 Figure S3: ESI-MS spectrum of 1 page S6 page S7 page S7 Characterization of 2 Figure S4: 1 H NMR spectrum of 2 Figure S5: 13 C NMR spectrum of 2 Figure S6: ESI-MS spectrum of 2 page S8 page S9 page S9 Characterization of 3 Figure S7: 1 H NMR spectrum of 3 Figure S8: 13 C NMR spectrum of 3 Figure S9: MALDI/TOF-MS spectra of 3 page S10 page S11 page S12 Characterization of 4 Figure S10: 1 H NMR spectrum of 4 Figure S11: 13 C NMR spectrum of 4 Figure S12: MALDI/TOF-MS spectra of 4 Figure S13: Absorption, emission, excitation of 4 at 298 K and 77 K in 2-MeTHF page S13 page S14 page S15 page S16 Characterization of 5 Figure S14: 1 H NMR spectrum of 5 Figure S15: 13 C NMR spectrum of 5 Figure S16: APCI-MS spectrum of 5 page S17 page S18 page S18 S2
3 Characterization of P1 Figure S17: 1 H NMR spectrum of P1 Figure S18: Absorption, emission, excitation of P[BdP-OT] P1 at 298 K and 77 K in 2-MeTHF and in thin film Figure S19: Absorption spectra of P[BdP-OT] P1 in 2-MeTHF, DCM and toluene at 298 K Figure S20: Films DRX before and after thermal annealing page S19 page S20 page S20 page S21 Characterization of P2 Figure S21: 1 H NMR spectrum of P2 Figure S22: 1 H NMR spectrum of P2 Zoom on aromatic region Figure S23: Absorption, emission, excitation of P[sBdP-OT] P2 at 298 K and 77 K in 2-MeTHF and in thin film page S22 page S23 page S24 Thermal properties of P1 and P2 Figure S24: TGA thermograms of P1 and P2. page S25 Characterization of 6 Figure S25: 1 H NMR spectrum of 6 Figure S26: 13 C NMR spectrum of 6 Figure S27: APCI-MS spectrum of 6 page S26 page S27 page S27 Characterization of 7 Figure S28: 1 H NMR spectrum of 7 Figure S29: 13 C NMR spectrum of 7 Figure S30: APCI-MS spectrum of 7 page S28 page S29 page S29 Characterization of 8 Figure S31: 1 H NMR spectrum of 8 Figure S32: APCI-MS spectrum of 8 page S30 page S31 S3
4 Characterization of M1 Figure S33: 1 H NMR spectrum of M1 Figure S34: MALDI/TOF-MS spectra of M1 Figure S35: Absorption, emission, excitation of M1 at 298 K and 77 K in 2-MeTHF Figure S36: Optimized geometry (DFT, B3LYP) for M1 Figure S37: Representations of the frontier MOs for M1 with corresponding energies Figure S38: Computed oscillator strength (F) as a function of the calculated positions of the first 75 electronic transitions for M1 page S32 page S33 page S34 page S34 page S35 page S36 Characterization of M2 Figure S39: 1 H NMR spectrum of M2 Figure S40: MALDI/TOF-MS spectra of M2 Figure S41: Absorption, emission, excitation of M2 at 298 K and 77 K in 2-MeTHF Figure S42: Optimized geometry (DFT, B3LYP) for M2 Figure S43: Representations of the frontier MOs for M2 with corresponding energies Figure S44: Computed oscillator strength (F) as a function of the calculated positions of the first 75 electronic transitions for M2 page S37 page S38 page S39 page S39 page S40 page S41 S4
5 Characterization of 9 Figure S45: 1 H NMR spectrum of 9 Figure S46: MALDI/TOF-MS spectra of 9 Figure S47: Absorption, emission, excitation of 9 at 298 K and 77 K in 2-MeTHF page S42 page S43 page S44 Comparison between M1 and 9 Figure S48: Absorption and emission of M1 and 9 at 298 K in 2-MeTHF and in thin film page S45 TABLES Table S1: Percent distribution of MOs of M1 Table S2: Computed oscillator strengths (F), positions of the first electronic transitions and major contributions of M1 Table S3: Percent distribution of MOs of M2 Table S4: Computed oscillator strengths (F), positions of the first electronic transitions and major contributions of M2 Table S5: Lifetime data for M1 and 9 page S46 page S47 page S50 page S51 page S54 REFERENCES page S55 S5
6 Characterization of 1 N N B F F Figure S1: 1 H NMR spectrum of 1 (300 MHz, CDCl 3, d ppm) S6
7 Figure S2: 13 C NMR spectrum of 1 (75 MHz, CDCl 3, d ppm) Figure S3: ESI-MS spectrum of 1 S7
8 Characterization of 2 I N N B F F I Figure S4: 1 H NMR spectrum of 2 (300 MHz, CDCl 3, d ppm) S8
9 Figure S5: 13 C NMR spectrum of 2 (75 MHz, CDCl 3, d ppm) Figure S6: ESI-MS spectrum of 2 S9
10 Characterization of 3 Si N N B F F Si Figure S7: 1 H NMR spectrum of 3 (300 MHz, CDCl 3, d ppm) S10
11 Figure S8: 13 C NMR spectrum of 3 (75 MHz, CDCl 3, d ppm) S11
12 Figure S9: MALDI/TOF-MS full (top) and zoom (bottom) spectra of 3 S12
13 Characterization of 4 H N N B F F H Figure S10: 1 H NMR spectrum of 4 (300 MHz, CDCl 3, d ppm) S13
14 Figure S11: 13 C NMR spectrum of 4 (75 MHz, CDCl 3, d ppm) S14
15 Figure S12: MALDI/TOF-MS full (top) and zoom (bottom) spectra of 4 S15
16 Figure S13: Absorption (black), emission (red), excitation (blue) of 4 at 298 K and 77 K in 2-MeTHF S16
17 Characterization of 5 I S I Figure S14: 1 H NMR spectrum of 5 (300 MHz, CDCl 3, d ppm) S17
18 Figure S15: 13 C NMR spectrum of 5 (75 MHz, CDCl 3, d ppm) Figure S16: APCI-MS spectrum of 5 S18
19 Characterization of P1 N N B F F S n C 8 H 17 Figure S17: 1 H NMR spectrum of P1 (300 MHz, CDCl 3, d ppm) S19
20 Figure S18: Absorption (black), emission (red), excitation (blue) of P[BdP-OT] P1 at 298 K and 77 K in 2-MeTHF and in thin film Figure S19: Absorption spectra of P[BdP-OT] P1 in 2-MeTHF (red), DCM (blue) and toluene (black) at 298 K S20
21 Figure S20: Films DRX before (black) and after (red) thermal annealing (100 C, 10 min) S21
22 Characterization of P2 Z N N B F F Z S n C 8 H 17 Z = CH 3 or Figure S21: 1 H NMR spectrum of P2 (300 MHz, CDCl 3, d ppm) S22
23 Figure S22: 1 H NMR of P2 spectrum (300 MHz, CDCl 3, d ppm) Zoom on aromatic region S23
24 Figure S23: Absorption (black), emission (red), excitation (blue) of P[sBdP-OT] P2 at 298 K and 77 K in 2-MeTHF and in thin film S24
25 Thermal properties of P1 and P2. Figure S24: TGA thermograms of P1 and P2 - Experiments were performed under Argon at a heating rate of 10 C.min -1 S25
26 Characterization of 6 S (C 2 H 5 )C 6 H 12 C 6 H 12 (C 2 H 5 ) Figure S25: 1 H NMR spectrum of 6 (300 MHz, CDCl 3, d ppm) S26
27 Figure S26: 13 C NMR spectrum of 6 (75 MHz, CDCl 3, d ppm) Figure S27: APCI-MS spectrum of 6 S27
28 Characterization of 7 I S (C 2 H 5 )C 6 H 12 C 6 H 12 (C 2 H 5 ) Figure S28: 1 H NMR spectrum of 7 (300 MHz, CDCl 3, d ppm) S28
29 Figure S29: 13 C NMR spectrum of 7 (75 MHz, CDCl 3, d ppm) Figure S30: APCI-MS spectrum of 7 S29
30 Characterization of 8 I S Figure S31: 1 H NMR spectrum of 8 (300 MHz, CDCl 3, d ppm) S30
31 Figure S32: APCI-MS spectrum of 8 S31
32 Characterization of M1 S R 2 N N R 2 B F F S R 2 R 2 R 2 = Figure S33: 1 H NMR spectrum of M1 (300 MHz, CDCl 3, d ppm) S32
33 Figure S34: MALDI/TOF-MS full (top) and zoom (bottom) spectrum of M1 S33
34 Figure S35: Absorption (black), emission (red), excitation (blue) of M1 at 298 K, 77 K in 2-MeTHF and in thin film Figure S36: Optimized geometry (DFT, B3LYP) for M1 S34
35 Figure S37: Representations of the frontier MOs for M1 with corresponding energies S35
36 Figure S38: Computed oscillator strength (F) as a function of the calculated positions of the first 75 electronic transitions for M1 S36
37 Characterization of M2 S S R 2 N N R 2 R 2 = R 2 B R 2 F F Figure S39: 1 H NMR spectrum of M2 (300 MHz, CDCl 3, d ppm) S37
38 Figure S40: MALDI/TOF-MS full (top) and zoom (bottom) spectra of M2 S38
39 Figure S41: Absorption (black), emission (red), excitation (blue) of M2 at 298 K, 77 K in 2-MeTHF and in thin film Figure S42: Optimized geometry (DFT, B3LYP) for M2 S39
40 Figure S43: Representations of the frontier MOs for M2 with corresponding energies S40
41 Figure S44: Computed oscillator strength (F) as a function of the calculated positions of the first 75 electronic transitions for M2 S41
42 Characterization of 9 S N N R 1 B F F S R 1 R 1 = Figure S45: 1 H NMR spectrum of 9 (300 MHz, CDCl 3, d ppm) S42
43 Figure S46: MALDI/TOF-MS full (top) and zoom (bottom) spectra of 9 S43
44 Figure S47: Absorption (black), emission (red), excitation (blue) of 9 at 298 K, 77 K in 2-MeTHF and in thin film S44
45 Comparison between M1 and 9 Figure S48: Absorption (solid) and emission (dashed) of M1 (red) and 9 (blue) at 298 K in 2-MeTHF and in thin film S45
46 Table S1: Percent distribution of MOs over selected molecular fragments of M1 H-4 H-3 H-2 H-1 HOMO LUMO L+1 L+2 L+3 L+4 Energy (ev) Alkyl / Aryl BODIPY Alkyne Thiophene S46
47 Table S2: Computed oscillator strengths (F), positions of the first electronic transitions and major contributions of M1 Transition Wavelength No. (nm) Osc. Strength Major contributions HOMO LUMO (98%) H-1 LUMO (99%) H-2 LUMO (91%) H-5 LUMO (99%) H-6 LUMO (72%), H-3 LUMO (21%) H-6 LUMO (18%), H-3 LUMO (79%) H-4 LUMO (96%) H-7 LUMO (19%), HOMO L+1 (75%) H-7 LUMO (73%), HOMO L+1 (15%) H-8 LUMO (26%), HOMO L+2 (64%) H-8 LUMO (69%), HOMO L+2 (26%) H-1 L+1 (94%) H-9 LUMO (91%) H-10 LUMO (91%) H-1 L+2 (83%) HOMO L+3 (97%) H-1 L+6 (22%), HOMO L+5 (63%) H-1 L+5 (30%), HOMO L+6 (59%) H-2 L+1 (89%) HOMO L+4 (92%) H-11 LUMO (17%), H-2 L+2 (77%) H-11 LUMO (67%), H-2 L+2 (18%) H-1 L+3 (97%) H-3 L+1 (41%), H-3 L+2 (45%) H-4 L+1 (59%), H-4 L+2 (26%) H-1 L+4 (99%) H-2 L+3 (92%) H-14 LUMO (60%), H-12 LUMO (36%) H-13 LUMO (87%) H-10 L+2 (13%), H-9 L+1 (17%), H-8 L+2 (13%), H-7 L+1 (18%) H-10 L+1 (20%), H-9 L+2 (19%), H-8 L+1 (19%), H-7 L+2 (16%) H-14 LUMO (34%), H-12 LUMO (56%) H-15 LUMO (81%) H-5 L+1 (85%) HOMO L+8 (24%), HOMO L+10 (21%) H-3 L+1 (41%), H-3 L+2 (33%) S47
48 H-3 L+2 (11%), H-1 L+10 (10%), HOMO L+7 (21%), HOMO L+9 (16%), HOMO L+11 (12%) H-5 L+2 (84%) H-4 L+1 (32%), H-4 L+2 (65%) H-16 LUMO (81%) H-1 L+5 (36%), HOMO L+6 (25%) H-18 LUMO (59%) H-1 L+6 (35%), HOMO L+5 (18%) H-17 LUMO (13%), H-6 L+3 (34%), H-5 L+4 (29%) H-19 LUMO (18%), H-17 LUMO (55%) H-19 LUMO (11%), H-1 L+5 (12%), HOMO L+7 (17%), HOMO L+9 (13%) H-6 L+1 (81%) H-19 LUMO (15%), H-2 L+4 (60%) H-19 LUMO (11%), H-2 L+4 (26%), HOMO L+7 (20%) H-6 L+2 (89%) H-32 LUMO (73%) H-24 LUMO (17%), H-20 LUMO (23%), H- 19 LUMO (17%) HOMO L+8 (30%), HOMO L+10 (20%) H-21 LUMO (71%), H-20 LUMO (19%) H-24 LUMO (21%), H-23 LUMO (12%), H- 20 LUMO (43%) H-10 L+1 (13%), H-9 L+2 (13%), H-8 L+1 (15%), H-7 L+2 (12%), HOMO L+11 (19%) H-7 L+1 (28%), H-1 L+7 (37%), HOMO L+8 (15%) H-22 LUMO (72%) H-29 LUMO (14%), H-28 LUMO (11%), H- 27 LUMO (10%), H-25 LUMO (10%), H- 22 LUMO (22%) H-8 L+1 (25%), H-7 L+1 (17%), H-7 L+2 (25%), H-1 L+7 (14%) H-8 L+1 (17%), H-7 L+1 (15%), H-7 L+2 (17%), H-1 L+7 (26%) H-25 LUMO (10%), H-24 LUMO (10%), H- 23 LUMO (54%) H-8 L+2 (26%), HOMO L+11 (10%) H-3 L+5 (25%), H-3 L+6 (33%) H-8 L+2 (27%), HOMO L+9 (13%), HOMO L+11 (18%) H-4 L+5 (43%), H-4 L+6 (29%) H-26 LUMO (90%) S48
49 H-27 LUMO (10%), H-25 LUMO (55%), H- 24 LUMO (16%), H-23 LUMO (10%) H-40 LUMO (91%) H-2 L+5 (79%), H-1 L+6 (13%) H-3 L+3 (91%) H-39 LUMO (94%) H-2 L+6 (23%), H-1 L+8 (47%) H-4 L+3 (89%) H-2 L+6 (56%), H-1 L+8 (17%) S49
50 Table S3: Percent distribution of MOs over selected molecular fragments of M2 H-4 H-3 H-2 H-1 HOMO LUMO L+1 L+2 L+3 L+4 Energy (ev) Alkyl / Aryl BODIPY Alkyne Thiophene S50
51 Table S4: Computed oscillator strengths (F), positions of the first electronic transitions and major contributions of M2 Transition Wavelength No. (nm) Osc. Strength Major contributors HOMO LUMO (98%) H-1 LUMO (97%) H-2 LUMO (97%) H-3 LUMO (92%) HOMO L+1 (91%) HOMO L+2 (94%) H-9 LUMO (99%) H-4 LUMO (99%) H-5 LUMO (99%) H-10 LUMO (29%), H-8 LUMO (11%), H- 7 LUMO (55%) H-6 LUMO (96%) H-8 LUMO (79%), H-7 LUMO (19%) H-10 LUMO (66%), H-7 LUMO (17%) H-11 LUMO (93%) H-1 L+1 (78%) H-2 L+1 (15%), H-1 L+2 (49%), HOMO L+3 (23%) H-12 LUMO (89%) H-2 L+1 (32%), H-1 L+2 (40%), HOMO L+3 (19%) H-2 L+2 (70%) H-2 L+1 (35%), HOMO L+3 (43%) H-14 LUMO (72%), H-13 LUMO (15%) H-3 L+1 (34%), H-2 L+2 (11%), HOMO L+4 (39%) H-15 LUMO (39%), H-14 LUMO (14%), H- 13 LUMO (38%) HOMO L+5 (98%) H-3 L+2 (81%) H-3 L+1 (49%), HOMO L+4 (39%) H-15 LUMO (56%), H-13 LUMO (28%) H-5 L+1 (27%), H-4 L+1 (43%) H-5 L+1 (21%), H-5 L+2 (30%), H-4 L+1 (15%), H-4 L+2 (16%) HOMO L+6 (87%) H-1 L+3 (60%) H-2 L+3 (25%), H-1 L+4 (17%), HOMO L+10 (24%) S51
52 H-2 L+3 (18%), H-1 L+3 (14%), HOMO L+9 (33%) H-6 L+1 (25%), H-6 L+2 (53%) H-8 L+1 (41%), H-8 L+2 (14%), H-7 L+1 (26%) H-2 L+3 (22%), HOMO L+9 (15%), HOMO L+10 (18%) H-8 L+1 (25%), H-7 L+1 (53%) H-5 L+1 (35%), H-5 L+2 (25%), H-4 L+1 (19%), H-4 L+2 (20%) H-4 L+2 (15%), HOMO L+7 (62%) H-5 L+2 (34%), H-4 L+2 (34%), HOMO L+7 (10%) H-8 L+2 (14%), H-7 L+2 (55%) HOMO L+8 (78%) H-9 L+1 (87%) H-11 L+2 (16%), H-9 L+2 (21%), H-1 L+4 (10%) H-1 L+4 (22%), H-1 L+5 (52%) H-9 L+2 (32%), H-1 L+4 (14%), H-1 L+5 (41%) H-11 L+2 (12%), H-9 L+2 (36%) H-16 LUMO (31%), H-2 L+4 (31%) H-16 LUMO (11%), H-6 L+1 (50%), H- 6 L+2 (24%) H-16 LUMO (40%), H-6 L+1 (15%), H- 2 L+4 (21%) H-14 L+1 (24%), H-14 L+2 (11%), H- 12 L+1 (16%), H-10 L+1 (10%) H-2 L+5 (95%) H-8 L+1 (19%), H-8 L+2 (59%), H-7 L+2 (15%) H-10 L+1 (78%) H-10 L+2 (11%), H-3 L+3 (69%), H-2 L+4 (12%) H-11 L+2 (11%), H-10 L+2 (70%) H-19 LUMO (11%), H-18 LUMO (77%) H-19 LUMO (45%), H-18 LUMO (17%), H- 17 LUMO (36%) H-1 L+6 (95%) H-19 LUMO (38%), H-17 LUMO (51%) H-20 LUMO (38%), HOMO L+13 (11%) H-20 LUMO (24%), HOMO L+12 (16%), HOMO L+13 (19%) H-3 L+4 (20%), HOMO L+11 (26%), S52
53 HOMO L+13 (14%) H-20 LUMO (13%), H-3 L+4 (28%), HOMO L+12 (11%) H-2 L+9 (16%), H-1 L+10 (18%), HOMO L+9 (12%) H-2 L+10 (10%), H-1 L+9 (16%) H-25 LUMO (11%), H-23 LUMO (11%), H- 21 LUMO (11%), HOMO L+13 (13%) H-11 L+1 (62%), H-11 L+2 (16%) H-2 L+6 (90%) H-21 LUMO (68%) H-5 L+3 (29%), H-5 L+4 (10%), H-4 L+3 (18%) H-5 L+3 (14%), H-4 L+3 (23%), H-4 L+4 (11%) H-24 LUMO (18%), H-12 L+1 (18%), HOMO L+14 (13%) H-24 LUMO (57%) H-23 LUMO (48%), H-22 LUMO (43%) S53
54 Table S5: Lifetime data for M1 and 9 λ ex (nm) λ em (nm) τ ± (ns) χ K 77 K 298 K 77 K 298 K 77 K 298 K 77 K M ± 0.20 (100 %) 3.07 ± 0.37 (100 %) ± 0.15 (100 %) 3.42 ± 0.16 (100 %) S54
55 SI reference 1. Xia, H. R.; Li, J.; Sun, W. T.; Peng, L. M., Organohalide lead perovskite based photodetectors with much enhanced performance. Chem Commun 2014, 50 (89), S55
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