Bis(perylene diimide) with DACH bridge as nonfullerene. electron acceptor for organic solar cells

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1 Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Supporting Information for Bis(perylene diimide) with DACH bridge as nonfullerene electron acceptor for organic solar cells Guangpeng Gao, ab Xiaolong Zhang, cde Dong Meng, ab Andong Zhang, ab Yanxia Liu, e Wei Jiang,* a Yanming Sun* cd and Zhaohui Wang a a. Beijing ational Laboratory for Molecular Science, Key Laboratory of rganic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing , P. R. China b. University of Chinese Academy of Sciences, Beijing , P. R. China c. Key Laboratory of Bio-Inspired Smart Interfacial Science and Technology of Ministry of Education, Beijing Key Laboratory of Bio-inspired Energy Materials and Devices, School of Chemistry and Environment, Beihang University, Beijing , P. R. China d. Heeger Beijing Research and Development Center, International Research Institute for Multidisciplinary Science, Beihang University, Beijing , P. R. China e. College of Physics, Liaoning University, o. 66 Chongshan Zhong Road, Huanggu District, Shenyang, P. R. China jiangwei@iccas.ac.cn -S1 -

2 Theoretical calculations Figure S1. Chemical structures of PTB7-Th (a) and DACH-PPDIs (b). ptimized geometries of DACH-PPDI by DFT at the ωb97xd/6-31g(d) level (c, d) and APFD/6-31G(d) level (e, f). 1 ptical, electrochemical and thermal Properties of DACH-PPDIs (a) ε (M -1 cm -1 ) a 2b 2c 3a 3b 3c (b) 1.4 ε (M -1 cm -1 ) a (in solution) 2a (in film) PTB7-Th PTB7-Th:2a Wavelength (nm) Wavelength (nm) -S2 -

3 (c) b(in solution) 2b(in film) PTB7-Th PTB7-Th:2b (d) c(in solution) 2c(in film) PTB7-Th PTB7-Th:2c ε (M -1 cm -1 ) ε (M -1 cm -1 ) Wavelength (nm) Wavelength (nm) 1.6 (e) 1.4 ε(m -1 cm -1 ) a(in solution) 3a(in film) PTB7-Th PTB7-Th:3a (f) 2.0 ε(m -1 cm -1 ) b(in solution) 3b(in film) PTB7-Th PTB7-Th:3b Wavelength (nm) Wavelength (nm) (g) c(in solution) 3c(in film) PTB7-Th PTB7-Th:3c ε(m -1 cm -1 ) Wavelength (nm) Figure S2. a) UV-Vis absorption spectra of 2 and 3 in chloroform solution (10 5 M). ormalized UV-Vis absorption spectra of b) 2a in solution, 2a and PTB7-Th in film on quartz substrate, PTB7-Th:2a blend film. c) 2b in solution, 2b and PTB7-Th in film on quartz substrate, PTB7- Th:2b blend film. d) 2c in solution, 2c and PTB7-Th in film on quartz substrate, PTB7-Th:2c blend film. e) 3a in solution, 3a and PTB7-Th in film on quartz substrate, PTB7-Th:3a blend film. f) 3b in solution, 3b and PTB7-Th in film on quartz substrate, PTB7-Th:3b blend film. g) 3c in solution, 3c and PTB7-Th in film on quartz substrate, PTB7-Th:3c blend film. -S3 -

4 (a) Current ( A) 2a 2b 2c 3a 3b 3c (b) Current ( A) 2a 2b 2c 3a 3b 3c Potential (V) Potential (V) Figure S3. CVs of DACH-PPDIs in solution (a) and film (b). CVs were calibrated by the Fc/Fc + as the redox couple and oxidation were from the reference compound ferrocene. Figure S4 a) Energy levels of IT, Zn, DACH-PPDIs, PTB7-Th, Mo 3, and Al. b) The device architecture of non-fullerene SCs. 100 Weight (%) a 2b 2c 3a 3b 3c Temperature ( ) Figure S5. TGAs of DACH-PPDIs under nitrogen flow. -S4 -

5 θ CD (mdeg) a 2b 2c θ CD (mdeg) a 3b 3c Wavelength (nm) Wavelength (nm) Figure S6. CD spectra of DACH-PPDIs in chloroform solution (10 5 M) Photovoltaic performances Figure S7. Tapping mode AFM height images (top) and phase images (bottom) of the active layers based on PTB7-Th:DACH-PPDIs, all images are 3 μm 3 μm 0 (a) Currrent Density (ma/cm 2 ) :1 1:1.5 1:2 1:2.5 PTB7-Th:2a Voltage(V) (b) Currrent Density (ma/cm 2 ) :1 1:1.5 1:2 1: PTB7-Th:2b Voltage (V) 0 (c) Currrent Density(mA/cm 2 ) :1 1:1.5 1:2 1:2.5 PTB7-Th:2c Voltage (V) 0 (d) Currrent Density (ma/cm 2 ) :1 1:1.5 1:2 1:2.5 PTB7-Th:3a Voltage (V) -S5 -

6 (e) Currrent Density (ma/cm 2 ) :1 1:1.5 1:2 1:2.5 PTB7-Th:3b Voltage (V) (g) Currrent Density(mA/cm 2 ) :1 1:1.5 1:2 1:2.5 PTB7-Th:3c Voltage (V) Figure S8. J-V curves of non-fullerene SCs based on PTB7-Th with 2 and 3 by different ratio Currrent Density (ma/cm 2 ) PTB7-Th:2c PTB7-Th:3a PTB7-Th:3b PTB7-Th:3c Voltage (V) Figure S9. J-V curves of non-fullerene SCs based on PTB7-Th with 2c and 3a-3c, respectively. (1:2 ratio, w:w) (a) Current Density (ma/cm^2) 1000 PTB7-Th:2a PTB7-Th:2b PTB7-Th:2c electron mobility Voltage (V) (b) Current Density (ma/cm^2) PTB7-Th:2a PTB7-Th:2b PTB7-Th:2c hole mobility Voltage (V) (c) Current Density (ma/cm^2) 1000 PTB7-Th:3a PTB7-Th:3b PTB7-Th:3c electron mobility (d) Current Density (ma/cm^2) PTB7-Th:3a PTB7-Th:3b PTB7-Th:3c hole mobility Voltage (V) Voltage (V) Figure 10. Measured space-charge-limited J V characteristics of PTB7-Th:DACH-PPDIs blend films under dark conditions for electron-only devices and hole-only devices -S6 -

7 Table S1. Photophysical, electrochemical and thermal properties of DACH-PPDIs λ max sol. ε λ max film E g E onset re E LUM E HM T deg [nm] a [M -1 cm -1 ] a [nm] b [ev] c [V] d [ev] e [ev] f [ºC] g 2a b c a b c a Measured in dilute CHCl 3 solution ( M). b Measured in spin-coating film from CHCl 3 solution. c Calculated by the onset of absorption in CHCl 3 solution according to E g (ev) = (1240/λ onset ). d In CH 2 Cl 2 solution vs. Fc/Fc +. e LUM (ev) estimated by the onset of the reduction peaks and calculated according to E LUM = -(4.8 + E re onset ) ev. f HM (ev) calculated according to E HM = (E LUM - E g ) ev. g Decomposition temperature determined by TGA corresponding to 5% weight loss at 10 ºC/min under nitrogen flow. Table S2. The performances of PTB7-Th:2c blend based devices (1:2, w/w) under different annealing temperature Annealing temperature ratio (ºC) V oc J sc FF PCE (V) (ma cm -2 ) (%) (%) a 1: ± ± ± ± 0.05 (3.00) 1: ± ± ± ± 0.20 (4.68) 1: ± ± ± ± 0.10 (3.48) a Tested under the illumination of AM 1.5 G 100 mw/cm 2. The values in parentheses refer to the max PCEs obtained from over five devices. Table S3. The detailed photovoltaic values of the non-fullerene devices with an inverted structure based on PTB7-Th:DACH-PPDIs 2 and 3 by different ratios (w/w), under the annealing temperature of 70 ºC ratio V oc (V) J sc (ma cm -2 ) FF (%) PCE (%) a 1: ± ± ± ± 0.11 (3.25) PTB7-Th/2a 1: ± ± ± ± 0.10 (3.81) 1: ± ± ± ± 0.15 (4.36) -S7 -

8 1: ± ± ± ± 0.11 (3.05) ratio V oc (V) J sc (ma cm -2 ) FF (%) PCE (%) 1: ± ± ± ± 0.14 (3.91) PTB7-Th/2b 1:1.5 1: ± ± ± ± ± 0.19 (4.01) ± ± ± 0.11 (4.42) 1: ± ± ± ± 0.13 (3.24) ratio V oc (V) J sc (ma cm -2 ) FF (%) PCE (%) 1: ± ± ± ± 0.21 (3.81) PTB7-Th/2c 1:1.5 1: ± ± ± ± ± 0.19 (4.29) ± ± ± 0.20 (4.68) 1: ± ± ± ± 0.16 (2.38) ratio V oc (V) J sc (ma cm -2 ) FF (%) PCE (%) 1: ± ± ± ± 0.17 (1.09) PTB7-Th/3a 1: ± ± ± ± 0.20 (2.95) 1: ± ± ± ± 0.05 (3.87) 1: ± ± ± ± 0.05 (2.84) -S8 -

9 ratio V oc (V) J sc (ma cm -2 ) FF (%) PCE (%) 1: ± ± ± ± 0.12 (1.92) PTB7-Th/3b 1: ± ± ± ± 0.23 (2.69) 1: ± ± ± ± 0.06 (3.85) 1: ± ± ± ± 0.09 (3.17) ratio V oc (V) J sc (ma cm -2 ) FF (%) PCE (%) 1: ± ± ± ± 0.16 (1.97) PTB7-Th/3c 1: ± ± ± ± 0.06 (2.66) 1: ± ± ± ± 0.06 (3.97) 1: ± ± ± ± 0.16 (2.07) a Tested under the illumination of AM 1.5 G 100 mw/cm 2. The values in parentheses refer to the max PCEs obtained from over five devices. References: 1. (a) J. -D. Chai and M. Head-Gordon, Phys. Chem. Chem. Phys.,2008, 10, ; (b) A. Austin, G. A. Petersson, M. J. Frisch, F. J. Dobek, G. Scalmani, and K. Throssell, J. Chem. Theory Comput., 2012, 8, ; (c) M. M. Francl, W. J. Pietro, W. J. Hehre, J. S. Binkley, M. S. Gordon, D. J. DeFrees and J. A. Pople, J. Chem. Phys., 1982, 77, ; (d) Gaussian 09, Revision D.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. akatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. akajima, Y. Honda,. Kitao, H. akai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. gliaro, M. Bearpark, J. J. Heyd, E. Brothers, K.. Kudin, V.. Staroverov, T. Keith, R. Kobayashi, J. ormand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi,. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann,. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. chterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels,. Farkas, J. B. Foresman, J. V. rtiz, J. Cioslowski, and D. J. Fox, Gaussian, Inc., Wallingford CT, S9 -

10 1 H MR spectrum of 2a in CDCl 3 (400 MHz, 25 ºC). GGP fR ppm H MR spectrum of 2b in CDCl 3 (400 MHz, 25 ºC). -S10 -

11 GGP fS ppm H MR spectrum of 2c in CDCl 3 (400 MHz, 25 ºC). GGP f ppm H MR spectrum of 3a in CDCl 3 (400 MHz, 25 ºC). -S11 -

12 GGP C77-R ppm H MR spectrum of 3b in CDCl 3 (400 MHz, 25 ºC). GGP C77-S ppm H MR spectrum of 3c in CDCl 3 (400 MHz, 25 ºC). -S12 -

13 GGP C ppm C MR spectrum of 2a in CDCl 3 (100 MHz, 25 ºC) GGP FR ppm 13 C MR spectrum of 2b in CDCl 3 (100 MHz, 25 ºC). -S13 -

14 F-S ppm 13 C MR spectrum of 2c in CDCl 3 (100 MHz, 25 ºC) GGP F ppm 13 C MR spectrum of 3a in CDCl 3 (100 MHz, 25 ºC). -S14 -

15 C77R ppm 13 C MR spectrum of 3b in CDCl 3 (100 MHz, 25 ºC) C77S ppm 13 C MR spectrum of 3c in CDCl 3 (100 MHz, 25 ºC). -S15 -

16 C ppm HRMS spectrum of 2a. -S16 -

17 HRMS spectrum of 2b. -S17 -

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19 HRMS spectrum of 2c. -S19 -

20 HRMS spectrum of 3a. -S20 -

21 HRMS spectrum of 3b. HRMS spectrum of 3c. -S21 -

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