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1 Electronic Supporting Information Naphtho[1,2-c:5,6-c ]bis[1,2,5]thiadiazole-based Nonfullerene Acceptors: Effect of Substituents on the Thiophene Unit on Properties and Photovoltaic Characteristics Shreyam Chatterjee, Yutaka Ie,*, and Yoshio Aso*, The Institute of Scientific and Industrial Research (ISIR), Osaka University, 8-1 Mihogaoka, Ibaraki, Osaka , Japan S1
2 Table of Contents Supplementary Figures and Tables NMR Spectra Computational Details S3 S7 S8 S23 S24 S34 S2
3 Supplementary Figures and Tables Figure S1. (a) TGA and (b) DSC curves of NTz-T H-Np (black), NTz-T F-Np (green), NTz-T hex- Np (red), and NTz-T eh-np (blue) with a heating rate of 10 C min 1 in N 2. S3
4 Figure S2. DPV of NTz-T H-Np (black), NTz-T F-Np (green), NTz-T hex-np (red), and NTz-T eh- Np (blue) in o-dcb/ch 3CN (10:1) solution containing 0.1 M TBAPF 6. Black dots indicate the position of reduction peaks. Figure S3. Calculated structures and molecular orbitals of model compounds for NTz-T H-Np, NTz-T F-Np, and NTz-T hex-np. 2-Ethylhexyl groups in the Np units were replaced with methyl groups to ease the calculation. S4
5 Figure S4. Supplementary J V curves of (a) P3HT:NTz-T H-Np, (b) P3HT:NTz-T F-Np, (c) P3HT:NTz-T hex-np, and (d) P3HT:NTz-T eh-np devices under illumination (solid line) and in the dark (dashed line). Table S1 OSC performance based on P3HT:NTz-T H-Np blend films. run V OC J SC FF PCE /V /ma cm 2 /% average 0.83 ± ± ± ± 0.01 S5
6 Table S2 OSC performance based on P3HT:NTz-T F-Np blend films. run V OC J SC FF PCE /V /ma cm 2 /% average 0.71 ± ± ± ± 0.01 Table S3 OSC performance based on P3HT:NTz-T hex-np blend films. run V OC J SC FF PCE /V /ma cm 2 /% average 0.92 ± ± ± ± 0.01 Table S4 OSC performance based on P3HT:NTz-T eh-np blend films. run V OC J SC FF PCE /V /ma cm 2 /% average 091± ± ± ± 0.02 S6
7 Figure S5. J 1/2 V measurements of (a) hole-only device and (b) electron-only device for P3HT:NTz-T H-Np (black), (b) P3HT:NTz-T F-Np (green), (c) P3HT:NTz-T hex-np (red), and (d) P3HT:NTz-T eh-np (blue) films. Figure S6. AFM phase images of (a) P3HT:NTz-T H-Np, (b) P3HT:NTz-T F-Np, (c) P3HT:NTz- T hex-np, and (d) P3HT:NTz-T eh-np films. S7
8 NMR Spectra Figure S7. 1 H NMR spectrum of Br-Np in CDCl 3. S8
9 Figure S8. 13 C NMR spectrum of Br-Np in CDCl 3. S9
10 Figure S9. 1 H NMR spectrum of 2 in CDCl 3. S10
11 Figure S C NMR spectrum of 2 in CDCl 3. S11
12 Figure S11. 1 H NMR spectrum of Br-T H-Np in CDCl 3. S12
13 Figure S C NMR spectrum of Br-T H-Np in CDCl 3. S13
14 Figure S13. 1 H NMR spectrum of Br-T F-Np in CDCl 3. S14
15 Figure S C NMR spectrum of Br-T F-Np in CDCl 3. S15
16 Figure S15. 1 H NMR spectrum of NTz-T H-Np in CDCl 3. S16
17 Figure S C NMR spectrum of NTz-T H-Np in CDCl 3. S17
18 Figure S17. 1 H NMR spectrum of NTz-T F-Np in CDCl 3. S18
19 Figure S C NMR spectrum of NTz-T F-Np in CDCl 3. S19
20 Figure S19. 1 H NMR spectrum of NTz-T hex-np in CDCl 3. S20
21 Figure S C NMR spectrum of NTz-T hex-np in CDCl 3. S21
22 Figure S21. 1 H NMR spectrum of NTz-T eh-np in CDCl 3. S22
23 Figure S C NMR spectrum of NTz-T eh-np in CDCl 3. S23
24 Computational Details All the calculations were conducted by using Gaussian 09 program. The geometry was optimized with the restricted Becke Hybrid (B3LYP) at 6-31 G (d, p) level. The TD-DFT calculation was conducted at the CAM B3LYP/6-31G (d, p) level of theory. All the alkyl groups were replaced with methyl groups for the ease of estimation. The calculated excited state of model compound for NTz-T H-Np at B3LYP/6-31G (d, p) level: Excited State 1: Singlet-A 2.15 ev (576 nm) f = HOMO 2 LUMO HOMO LUMO Excited State 3: Singlet-A 3.22 ev (384 nm) f = HOMO 3 LUMO HOMO 1 LUMO HOMO LUMO Optimized structure of model compound for NTz-T H-Np Centre Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S24
25 S25
26 S26
27 The calculated excited state of model compound for NTz-T F-Np at B3LYP/6-31G (d, p) level: Excited State 1: Singlet-A 2.26 ev (547 nm) f = HOMO 2 LUMO HOMO LUMO Excited State 3: Singlet-A 3.30 ev (376 nm) f = HOMO LUMO HOMO LUMO Optimized structure of model compound for NTz-T F-Np Centre Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S27
28 S28
29 S29
30 The calculated excited state of model compound for NTz-T hex-np at B3LYP/6-31G (d, p) level: Excited State 1: Singlet-A 2.12 ev (585 nm) f = HOMO 2 LUMO HOMO 1 LUMO HOMO LUMO Excited State 3: Singlet-A 3.17 ev (390 nm) f = HOMO 2 LUMO HOMO LUMO HOMO LUMO Optimized structure of model compound for NTz-T hex-np Centre Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S30
31 S31
32 S32
33 S33
34 S34
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