Phosphonic anchoring groups in organic dyes for solid-state solar cells
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1 Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics. This journal is the Owner Societies 2015 SUPPORTING INFORMATION Phosphonic anchoring groups in organic dyes for solid-state solar cells Antonio Abate, a,c, * Raquel Pérez Tejada, c Konrad Wojciechowski, a Jamie M. Foster, d Aditya Sadhanala, b Ullrich Steiner, b Henry J. Snaith, a, * Santiago Franco, c, * Jesús Orduna. c a Department of Physics, University of Oxford, Oxford, Parks Road,OX1 3PU, U.K. b Cavendish Laboratory, Department of Physics, University of Cambridge, 19 JJ Thomson Ave, Cambridge, CB3 0HE, UK c Instituto de Ciencia Materiales de Aragón, Departamento Química Orgánica, Universidad de Zaragoza-CSIC, Spain d Department of Mathematics & Statistics, McMaster University, Hamilton, Ontario, L8S 4K1, Canada. * Corresponding authors: AA antonioabate83@gmail.com, HJS h.snaith1@physics.ox.ac.uk, SF sfranco@unizar.es. KEYWORDS. Organic dyes, solid-state dye-sensitized solar cells, phosphonic acid anchoring group 1
2 INDEX - Computational details - NMR spectra - Absorption and emission spectra in tbuoh:ch 3 CN (1:1) - Electrochemical characterisation - Relative dye concentration on the TiO 2 surface - Dye solution calibration curves - Device performance parameters collected over 6 months of experiments 2
3 Computational details Pyt-COOH Optimized ground state geometry in DMF (CPCM-6-31G*/M06-2x) Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z
4 Pyt-COOH Optimized first excited state geometry in DMF (CPCM-TD-6-31G*/M06-2x) Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z
5 Pyt-COOH Calculated Absorption Spectrum in DMF (CPCM-TD-M06-2x/6-311+G(2d,p)//CPCM-M06-2x/6-31G*): No. Energy (cm-1) Wavelength (nm) f Major contribs HOMO->LUMO (97%) HOMO->L+1 (60%), HOMO->L+2 (25%) H-1->LUMO (6%) HOMO->L+1 (28%), HOMO->L+2 (47%) H-2->LUMO (9%), H-1->LUMO (9%) H-1->LUMO (69%), HOMO->L+2 (14%) H-2->LUMO (3%), H-1->L+1 (7%) H-2->LUMO (76%) H-5->LUMO (5%), HOMO->L+1 (7%), HOMO->L+2 (7%) H-7->LUMO (90%) H-7->L+7 (3%) 5
6 Pyt-PO(OH) 2 Optimized ground state geometry in DMF (CPCM-6-31G*/M06-2x) Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z
7 Pyt-PO(OH) 2 Optimized first excited state geometry in DMF (CPCM-TD-6-31G*/M06-2x) Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z
8 Pyt-PO(OH) 2 Calculated Absorption Spectrum in DMF (CPCM-TD-M06-2x/6-311+G(2d,p)//CPCM-M06-2x/6-31G*): No. Energy (cm-1) Wavelength (nm) f Major contribs HOMO->LUMO (97%) HOMO->L+1 (79%) H-1->LUMO (5%), HOMO->L+2 (7%) H-1->LUMO (12%), HOMO->L+1 (11%), HOMO->L+2 (63%) H-2->LUMO (6%) H-1->LUMO (68%), HOMO->L+2 (14%) H-2->LUMO (3%), H-1->L+1 (4%), H-1->L+2 (4%) H-2->LUMO (78%) H-5->LUMO (6%), HOMO->L+2 (9%) H-4->LUMO (41%), H-4->L+1 (23%) H-7->LUMO (3%), H-3->LUMO (4%), H-1->L+1 (4%), H-1->L+4 (3%), H-1->L+5 (2%), HOMO->L+4 (3%), HOMO->L+5 (3%) 8
9 Pyt-PO(OEt)OH Optimized ground state geometry in DMF (CPCM-6-31G*/M06-2x) Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z
10 Pyt-PO(OEt)OH Optimized first excited state geometry in DMF (CPCM-TD-6-31G*/M06-2x) Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z
11 Pyt-PO(OEt)OH Calculated Absorption Spectrum in DMF (CPCM-TD-M06-2x/6-311+G(2d,p)//CPCM-M06-2x/6-31G*): No. Energy (cm-1) Wavelength (nm) f Major contribs HOMO->LUMO (97%) HOMO->L+1 (80%) H-1->LUMO (5%), HOMO->L+2 (7%) H-1->LUMO (12%), HOMO->L+1 (11%),HOMO->L+2 (64%) H-2->LUMO (6%) H-1->LUMO (68%), HOMO->L+2 (14%), H-2->LUMO (3%), H-1->L+1 (4%), H-1->L+2 (4%) H-2->LUMO (78%), H-5->LUMO (6%),HOMO->L+2 (9%) H-7->LUMO (15%), H-4->LUMO (34%), H-4->L+1 (19%) H-3->LUMO (4%),H-1->L+1 (4%), H-1->L+4 (3%), HOMO->L+4 (3%), HOMO->L+5 (2%) 11
12 NMR spectra 1 H NMR spectrum of compound pyt-cooh (400 MHz, dmso-d 6 ) N S COOH CN Ph O Ph ppm (t1)
13 13 C NMR (APT) spectrum of compound pyt-cooh (100 MHz, dmso-d 6 ) N S COOH CN Ph O Ph ppm (t1)
14 1 H NMR spectrum of compound pyt-po(oh) 2 (400 MHz, dmso-d 6 ) OH O P OH N CN S Ph O Ph ppm (t1)
15 13 C NMR (APT) spectrum of compound pyt-po(oh) 2 (100 MHz, dmso-d 6 ) OH O P OH N CN S Ph O Ph ppm (t1)
16 1 H NMR spectrum of compound pyt-po(oet)oh (400 MHz, dmso-d 6 ) O O P OH N CN S Ph O Ph ppm (t1)
17 13 C NMR (APT) spectrum of compound pyt-po(oet)oh (100 MHz, dmso-d 6 ) N O O P OH CN S Ph O Ph ppm (t1)
18 Absorption and emission spectra in t BuOH:CH 3 CN (1:1) Absorption-Emission spectra 10-5 M in t BuOH:CH 3 CN (1:1) pyt-cooh Absorption-Emission spectra 10-5 M in t BuOH:CH 3 CN (1:1) pyt-po(oh) 2 18
19 Absorption-Emission spectra 10-5 M in t BuOH:CH 3 CN (1:1) pyt-po(oet)oh 19
20 Electrochemical characterization Differential pulse voltammetry (DPV) pyt-cooh in DMF 0,00004 pyt-cooh 0,00003 I (A) 0, , , ,0 0,5 1,0 1,5 E (V) Differential pulse voltammetry (DPV) pyt-po(oh) 2 in DMF pyt-po(oh)2 0,00002 I (A) 0, , ,0 0,5 1,0 1,5 E (V) 20
21 Differential pulse voltammetry (DPV) pyt-po(oet)oh in DMF 0, pyt-po(oet)oh 0, I (A) 0, , ,0 0,5 1,0 1,5 E (V) 21
22 Relative dye concentration on the TiO 2 surface To estimate the dye surface concentration on TiO 2 surface, we prepared three identical mesoporous TiO 2 films (thickness of the TiO 2 films 3 μm, area 0.36 cm 2 ) and about 0.1 mm dyeing solutions in 1:1 mixture of acetonitrile and tert-butyl alcohol of pyt-cooh and pyt- PO(OEt)OH. Then we measured the absorption of the dyeing solutions before and after soaking for 3 hours the TiO 2 films and made used of dye calibration curves (see next paragraph) to calculated the number of dye molecules left in solution and thus to estimate the relative dye concentration on TiO 2. All the details of the calculation are reported in the table below. As discussed in the main text pyt-po(oh) 2 is not stable in the dyeing solution, therefore we could not extract the relative dye concentration for this dye. pyt-cooh pyt-po(oet)oh before soaking after soaking before soaking after soaking Absorption maximum Molarity (M) 1.02E E E E-5 Moles in solution 3.56E E E E-7 Moles adsorbed on TiO 2 film 2.8E-8 1,9E-8 Relative dye concentration on TiO
23 Dye solution calibration curves Figure 1 2,0 1,5 Abs 1,0 pyt-cooh Abs 512 nm Exponential Value Standard Error Equation y = y0 + A*exp(R0*x) y0 1, , ,5 Reduced C 0,00964 A -2, ,11625 hi-sqr Adj. R-Squ 0,98002 R , , ,0 0,0 5,0x10-5 1,0x10-4 1,5x10-4 2,0x10-4 Concentration (M) Figure 2 23
24 Figure 3 Figure 4 24
25 3,5 3,0 2,5 Abs 2,0 1,5 1,0 0,5 pyt-po(oet)oh Abs 463 nm Exponential Value Standard Error Equation y = y0 + A*exp(R0*x) y0 19,5673 3,03405 Reduced C hi-sqr 2,75805E-4 A -19, ,02715 Adj. R-Squ 0,99974 R0-943, , ,0 0,0 5,0x10-5 1,0x10-4 1,5x10-4 2,0x10-4 Concentration (M) Figure 5 Figure 6 25
26 Figure 7 2,0 1,5 Abs 1,0 0,5 pyt-po(oh) 2 Abs 482 nm Exponential Value Standard Error Equation y = y0 + A*exp(R0*x) y0-2, ,31289 Reduced C 4,22859E-4 A 2, ,30294 hi-sqr Adj. R-Squ 0,99884 R0 3498, , ,0 0,0 5,0x10-5 1,0x10-4 1,5x10-4 2,0x10-4 Concentration (M) Figure 8 26
27 Figure 9 27
28 Device performance parameters collected over 6 months of experiments Box plot of the device performance parameters extracted from the current voltage curves collected under AM 1.5 simulated sunlight of 100 mw cm -2 equivalent solar irradiance, for over 40 devices prepared for each dye over a period of 6 months in several different experiments. We did plot the device performance parameters of all the devices in a single graph, which showed a relative narrow and a significant more spread data distribution for pyt- COOH and pyt-po(oet)oh respectively. The origin of such large data distribution is due to the fact that the device preparation procedure was constantly changed to optimize the performances. The best performance was achieved after tuning the concentration dying solution, the soaking time in the dying solution, the mesoporous TiO 2 thickness, the Spiro- OMeTAD concentration and additive composition. We kept track of all these change and we reported the optimized procedure in the Experimental section. 28
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