Supporting Information
Symmetrically Functionalized Diketopyrrolopyrrole with Alkylated Thiophene
Moiety: From Synthesis to Electronic Devices Applications
By Akshaya K. Palai, Jihee Lee, Minkyung Jea, Hanah Na, Tae Joo Shin, Soonmin Jang, Seung-Un
Park, Seungmoon Pyo*
*pyosm@kokuk.ac.kr
Contents:
1. Contents …………………………………………………………………………………S1
2. Materials and Instruments ……………………………………………….…………….S2
3.
1
H NMR,
13C
NMR, and HRMS Spectra of DPP(3HT)2...…………………….…S3
4. TGA thermogram of DPP(3HT)2………………….…………….…..………………..S4
5. Optimal geometry of DPP(3HT)2…..……………….…………………….…………….S4
6. References ………………………………………………………………….……………S5
S1
Materials: Starting compound 1SR1 and (3-hexylthiophen-2-yl)trimethylstannane (4)SR2 were prepared
as reported earlier. Compound (3) was prepared as per our earlier reported procedure.SR3 NBS was
recrystallized from water. N,N′-ditridecyl-3,4,9,10-perylenetetracarboxylic diimide (PTCDI-C13),
Pd(PPh3)4, anhydrous solvents (DMF and toluene) were procured from Sigma-Aldrich.
Instruments: 1H and 13C NMR spectra were measured in deuterated chloroform on a Bruker 400 MHz
and 100 MHz Avance spectrometer, respectively. Thermo LTQ-Orbitrap XL mass spectrometer was
used for high-resolution ESI-FTMS spectrum. UV-vis spectra were recorded on a Varian Cary 500
spectrometer. Cyclic voltamogram was recorded with a three-electrode system, consisting of a glassy
carbon electrode coated with a thin film of DPP(3HT)2 as working electrode, a platinum mesh counter
electrode, and a Ag/AgNO3 (0.1M) reference electrode (scan rate: 50 mV s-1) [Electrochemical
Interface & Impedance Analyzer (IVIUM Technologies)]. The solutions were prepared using a
degassed acetonitrile solution containing 0.05 M tetrabutylammonium hexafluorophosphate (Bu4NPF6)
as the electrolyte. Ferrocene was used as the internal standard. TGA was carried out using a TGA 7 TA
instrument (Perkin Elmer). Tapping mode atomic force microscope (AFM) (nanoscope IIIa, Digital
Instruments) was used to evaluate the morphology of the semiconductor film on various gate
dielectrics. Powder XRD was carried out using an incident X-ray energy of 11.24 keV (λ = 1.103 Å)
(PLS-II 9A U-SAXS beamline). DFT calculation was performed at the B3LPY/6-31G(d,p) level, using
Gaussian09.SR4 Electrical characteristics were measured under ambient conditions. A HP 4145B
semiconductor parameter analyzer was used for the same. A surface profiler (AMBIOS XP-100) was
use to measure the thickness of the gate dielectrics.
S2
Figure S1. 1H and 13C NMR (inset) spectra of DPP(3HT)2 in CDCl3.
Figure S2. High-resolution ESI-FT mass spectrum of DPP(3HT)2.
S3
Figure S3. TGA thermogram of DPP(3HT)2 under nitrogen atmosphere (scan rate: 10 °C min-1).
Figure S4. Optimized geometry of DPP(3HT)2 as calculated by DFT at the B3LPY/6-31G(d, p) level.
S4
References:
SR1. Y. Zou, D. Gendron, R. Badrou-Aich, A. Najari, Y. Tao and M. Lecrerc,
Macromolecules,
2009, 42, 2891-2894.
SR2. D. J. Crouch, D. Sparrowe, M. Heeney, I. McCulloch and P. J. Skabara, Macromol. Chem
. Phys., 2010, 211, 2642-2648.
SR3. A. K. Palai, J. Lee, S. Das, J. Lee, H. Cho, S.-U. Park and S. Pyo, Org. Electron., 2012, 1
3, 2553-2560.
SR4. Gaussian 09, Revision A.1, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb,
M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.;
Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.;
Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.;
Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A.; Peralta, Jr. J. E.; Ogliaro, F.; Bearpark, M.;
Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.;
Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.;
Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.;
Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J.
W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.;
Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J.
Gaussian, Inc., Wallingford CT, 2009.
S5