Effect of substituents on the electron transport properties of bay substituted perylene diimide derivatives
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1 Supporting information for Effect of substituents on the electron transport properties of bay substituted perylene diimide derivatives Sivamurugan Vajiravelu, a Lygaitis Ramunas, b Gražulevičius Juozas Vidas, b Gaidelis Valentas, c Jankauskas Vygintas c and Suresh Valiyaveettil*,a a Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore b Department Organic Technology, Kaunas University of Technology, Radvilenu pl. 19, LT-50254, Kaunas, Lithuania c Department of Solid State Electronics, Vilnius University, Sauletekio al. 9, LT-10222, Vilnius, Lithuania
2 Figure 1S 1 H NMR of 1,7-dibromo perylene ppm (f1) ppm (f1)
3 siva239 *** Current Data Parameters *** NAME : de02siva EXPNO : 1 PROCNO : 1 *** Acquisition Parameters *** DATE_t : 22:05:11 DATE_d : Dec NS : 24 SFO1 : MHz SOLVENT : CDCl3 *** Processing Parameters *** AQORDER : 0 *** 1D NMR Plot Parameters *** Start : ppm Stop : 0.00 ppm Integral Figure 2S 1 H NMR spectrum of 1,7-dibromo-N,N -dodecyl perylene bisimide (PDI)
4 3000 Intensity (a.u) Intensity (a.u) m/z m/z Figure 3S MALDI-TOF spectrum of 1,7-dibromo-N,N -dodecyl perylene bisimide (PDI)
5 Figure 4S. 1 H and 13 C NMR of PDI1 siva232 Bruker Integral *** Current Data Parameters *** NAME : nv20siva EXPNO : 1 PROCNO : 1 *** Acquisition Parameters *** DATE_t : 05:11:34 DATE_d : Nov DS : 0 NS : 24 O1 : Hz O2 : Hz O3 : Hz SFO1 : MHz SFO2 : MHz SFO3 : MHz SOLVENT : CDCl3 *** Processing Parameters *** AZFW : ppm *** 1D NMR Plot Parameters *** SR : Hz
6 13 C of PDI1 siva232 Bruker *** Current Data Parameters *** NAME : nv20siva EXPNO : 2 PROCNO : 1 *** Acquisition Parameters *** DATE_t : 05:14:26 DATE_d : Nov DS : 2 NS : O1 : Hz O2 : Hz O3 : Hz SFO1 : MH SFO2 : MH SFO3 : MH SOLVENT : CDCl3 *** Processing Parameters *** AZFW : ppm *** 1D NMR Plot Parameters *** SR : 1.02 Hz
7 Figure 5S. 1 H and 13 C NMR of PDI2 siva221 *** Current Data Parameters *** Integral NAME : oc29siva EXPNO : 2 PROCNO : 1 *** Acquisition Parameters *** BF1 : MHz DSLIST : SSSSSSSSSSSSSSS EXP : NS : 64 SFO1 : MHz SOLVENT : CDCl3 Integral Integral
8 13 C of PDI2 siva221 *** Current Data Parameters *** NAME : oc29siva EXPNO : 3 PROCNO : 1 *** Acquisition Parameters *** BF1 : MHz DSLIST : SSSSSSSSSSSSSSS EXP : NS : SFO1 : MHz SOLVENT : CDCl
9 Figure 6S. 1 H and 13 C NMR of PDI3 siva226 Bruker Integral *** Current Data Parameters *** NAME : nv05siva EXPNO : 2 PROCNO : 1 *** Acquisition Parameters *** DATE_t : 03:17:31 DATE_d : Nov NS : 64 SFO1 : MHz SOLVENT : CDCl3 *** Processing Parameters *** AQORDER : 0 *** 1D NMR Plot Parameters *** Start : ppm Stop : 0.00 ppm
10 13 C of PDI3 siva226 *** Current Data Parameters *** NAME : nv05siva EXPNO : 3 PROCNO : 1 *** Acquisition Parameters *** DATE_t : 03:20:26 DATE_d : Nov NS : 5244 SFO1 : MHz SOLVENT : CDCl3 *** Processing Parameters *** AQORDER : 0 *** 1D NMR Plot Parameters *** Start : ppm Stop : 0.00 ppm
11 Figure 7S. 1 H and 13 C NMR of PDI4 siva210 *** Current Data Parameters *** Integral NAME : oc28siva EXPNO : 3 PROCNO : 1 *** Acquisition Parameters *** DATE_t : 00:49:24 DATE_d : Oct NS : 24 SFO1 : MHz SOLVENT : CDCl3 *** Processing Parameters *** AQORDER : 0 *** 1D NMR Plot Parameters *** Start : ppm Stop : 0.00 ppm Integral
12 13 C of PDI4 siva210 *** Current Data Parameters *** NAME : oc28siva EXPNO : 6 PROCNO : 1 *** Acquisition Parameters *** DATE_t : 03:41:49 DATE_d : Oct NS : SFO1 : MHz SOLVENT : CDCl3 *** Processing Parameters *** AQORDER : 0 *** 1D NMR Plot Parameters *** Start : ppm Stop : 0.00 ppm
13 Figure 8S. 1 H and 13 C NMR of PDI5 siva213 *** Current Data Parameters *** Integral NAME : oc28siva EXPNO : 4 PROCNO : 1 *** Acquisition Parameters *** DATE_t : 00:55:24 DATE_d : Oct NS : 24 SFO1 : MHz SOLVENT : CDCl3 *** Processing Parameters *** AQORDER : 0 *** 1D NMR Plot Parameters *** Start : ppm Stop : 0.00 ppm Integral
14 13 C of PDI5 siva213 *** Current Data Parameters *** NAME : oc28siva EXPNO : 5 PROCNO : 1 *** Acquisition Parameters *** DATE_t : 00:58:56 DATE_d : Oct NS : 6648 SFO1 : MHz SOLVENT : CDCl3 *** Processing Parameters *** AQORDER : 0 *** 1D NMR Plot Parameters *** Start : ppm Stop : 0.01 ppm
15 8000 Intensity / a.u PDI MALDI-TOF of PDI1 m/z
16 PDI4 Intensity / a.u m / Z MALDI-TOF of PDI4
17 m/z PDI3 400 Intensity (a.u) m/z MALDI-TOF of PDI3
18 Absorbance (a.u) Solution state PDI PDI1 PDI2 PDI3 PDI4 PDI Wavelength (nm) Figure 9S. Absorption spectra in solution
19 Figure 10S. Absorption spectra of thin films Absorbance (a.u) 1.0 Spin coated thin film PDI1 PDI2 PDI3 PDI4 PDI Wavelength (nm)
20 Figure 11S. Emission spectra in solution Emission (a.u) PDI PDI1 PDI2 PDI4 PDI3 PDI Wavelength (nm)
21 Figure 12S. DSC curves of PDI1. Heating-cooling-heating curve. Recorded under nitrogen atmosphere Heat Flow < endo exo > PDI1 Tg 1 st cooling 1 st heating 2 nd heating Tm Temperature [ o C]
22 Figure 13S. DSC curves of PDI3. Heating-cooling-heating curve. Recorded under nitrogen atmosphere Heat Flow < endo egzo > PDI3 Tg Tm 1 st cooling 1 st heating 2 nd heating Temperature [ o C]
23 Figure 14S. DSC curves of PDI4. Heating-cooling-heating curve. Recorded under nitrogen atmosphere Heat Flow < endo egzo > 2 nd heating 1 st heating 1 st cooling PDI Temperature [ o C]
24 Figure 15S. XTOF transients for blend of PDI4and PC-Z. Arrow marks in insert indicates a transit time of holes J69, Al+[PDI4+(PC-Z), 3:1], d=5μm t =25 o C du/dt (a.u.) du/dt (a.u.) V U 0 : -492 V Pakaitinus 5 min V -452 V -404 V -396 V -336 V -300 V -224 V -104 V UV flash t (s) t (s)
25 Figure 16S. XTOF transients for blend of PDI5and PC-Z. Arrow marks in insert indicates a transit time of holes J70, Al+[PDI5+(PC-Z), 3:1], d=6μm t =25 o C U 0 : 10-1 du/dt (a.u.) du/dt (a.u.) V V -990 V -870 V -740 V -628 V -584 V UV flash t (s) t (s)
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