Supporting Information
Syntheses, Properties, and Field Effect Transistors of Small Band Gap Quinoxalineand Thienopyrazine-Vinylene/Ethynylene Conjugated Polymers
Chu-Chen Chueh,1. Mei-Hsiu Lai,1 Jung-Hsun Tsai,1 Chih-Feng Wang,1
and Wen-Chang Chen1,2,*
1: Department of Chemical Engineering, National Taiwan University, Taipei, Taiwan 106
2: Institute of Polymer Science and Engineering, National Taiwan University, Taipei,
Taiwan 106.
 To whom all correspondence should be addressed
 Tel: 886-2-23628398, Fax:886-2-23623040
E-mail:chenwc@ntu.edu.tw
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5,8-dibromo-2,3-bis-[4-(2-ethylhexyloxy)-phenyl]quinoxaline (AQ)[21]
A mixture of compound 1,2-bis[4-(2-ethylhexyloxy)phenyl]-1,2-ethanedione (2.92g,
6.3mmol), compound 3,6-dibromobenzene-1,2-diamine (2.0g, 7.5 mmol) and glacial acetic
acid (50ml) was heated at 80℃ under nitrogen overnight. After most of the solvent was
evaporated, the residue was washed with water. The combined aqueous phases were
extracted with dichloromethane and then dried by MgSO4. Evaporation of the solvent and
column chromatography (solvent, hexane : ethyl acetate (10:1)) yielded compound AQ
(3.5g, ~80%) as a yellow oil. 1H NMR (CDCl3), δ (ppm): 7.81 (s, 2H); 7.63 (d, 4H); 6.86 (d,
4H); 3.86 (d, 4H); 1.65-1.78 (m, 2H); 1.24-1.54 (m, 16H); 0.87-0.96 (m, 12H). (NMR is
shown in Figure S1)
5,8-dibromo-2,3-bis-[4-(2-ethylhexyloxy)-phenyl]-thieno[3,4-b]pyrazine (ATP)[22]
A solution of compound 2,3-bis-[4-(2-ethylhexyloxy)-phenyl]-thieno[3,4-b]pyrazine
(2g, 3.67mmol) in DMF (20ml) and NBS (1.3g, 7.4mmol) in DMF (10ml) were prepared
first. In the absence of light, the latter solution was slowly and dropwise added to the
former under nitrogen, and the mixture was stirred at -30℃ for 5hr. After the reaction, the
residue was poured onto ice, and extracted repeatedly with diethyl ether. The combined
organic phases were continuously washed with water and dried by MgSO4. Evaporation of
the solvent and chromatography (solvent, dichloromethane : hexane (1:2)) yielded
compound ATP (1.3g, ~50%). 1H NMR (CDCl3), δ (ppm): 7.43 (d, 4H); 6.83 (d, 4H); 3.86
(d, 4H); 1.70-1.75 (m, 2H); 1.27-1.53 (m, 16H); 0.87-0.98 (m, 12H). (NMR is shown in
Figure S2)
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Figure S1. 1H NMR spectra of 5,8-dibromo-2,3-diheptylquinoxaline (monomer AQ) in
CDCl3.
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Figure S2. 1H NMR spectra of 5,8-dibromo-2,3-bis-[4-(2-ethylhexyloxy)-phenyl]thieno[3,4-b]pyrazine (monomer ATP) in CDCl3.
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Figure S3. Atomic force microscopy height images of the PATPV (A~C) and PATPE
(D~F) films on different SAM-modified surface. The image size is 5 μm ×5 μm
and the data scale is 20nm.
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Figure S4. DSC curves of PATPV and PATPE under a nitrogen atmosphere at a
heating rate of 10 oC/min.
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