Page 9 of 11
Chemistry of Materials
(21) Treat, N. D.; Nekuda Malik, J. A.; Reid, O.; Yu, L.; Shuttle, C.
benzodithiophene Copolymers via Alkyl Side Chain
1
2
3
4
5
6
7
8
G.; Rumbles, G.; Hawker, C. J.; Chabinyc, M. L.; Smith, P.;
Stingelin, N., Microstructure Formation in Molecular and
Polymer Semiconductors Assisted by Nucleation Agents. Nat.
Mater. 2013, 12, 628-633.
Manipulation: Synthesis, Characterization and Photovoltaic
Properties. J. Mater. Chem. A, 2014, 2, 11162-11170.
(36) Zhang, J.; Cai, W.; Huang, F.; Wang, E.; Zhong, C.; Liu, S.;
Wang, M.; Duan, C.; Yang, T.; Cao, Y., Synthesis of Quinoxaline-
Based Donor-Acceptor Narrow-Band-Gap Polymers and Their
Cyclized Derivatives for Bulk-Heterojunction Polymer Solar Cell
Applications Macromolecules, 2011, 44, 894-901.
(37) Wang, E.; Hou, L.; Wang, Z.; Hellström, S.; Zhang, F.;
Inganäs, O.; Anersson, M., An easily Synthesized Blue Polymer
for High-Performance Polymer Solar Cells. Adv. Mater., 2010, 22,
5240-5244.
(38) Lee, B.-L.; Yamamoto, T., Syntheses of New Alternating Ct-
Type Copolymers of Thiophene and Pyrido[3,4-b]Pyrazine Units:
Their Optical and Electrochemical Properties in Comparison
with Similar Ct Copolymers of Thiophene with Pyridine and
Quinoxaline. Macromolecules 1999, 32, 1375-1382.
(39) Kroon, R.; Gehlhaar, R.; Steckler, T. T.; Henriksson, P.;
Mueller, C.; Bergqvist, J.; Hadipour, A.; Heremans, P.;
Andersson, M. R., New Quinoxaline and Pyridopyrazine-Based
Polymers for Solution-Processable Photovoltaics. Sol. Energy
Mater. Sol. Cells 2012, 105, 280-286.
(40) Zhang, X.; Shim, J. W.; Tiwari, S. P.; Zhang, Q.; Norton, J.
E.; Wu, P.-T.; Barlow, S.; Jenekhe, S. A.; Kippelen, B.; Bredas, J.-
L.; Marder, S. R., Dithienopyrrole-Quinoxaline/Pyridopyrazine
Donor-Acceptor Polymers: Synthesis and Electrochemical,
Optical, Charge-Transport, and Photovoltaic Properties. J.
Mater. Chem. 2011, 21, 4971-4982.
(41) Yuan, M.-C.; Chiu, M.-Y.; Chiang, C.-M.; Wei, K.-H.,
Synthesis and Characterization of Pyrido[3,4-b]Pyrazine-Based
Low-Bandgap Copolymers for Bulk Heterojunction Solar Cells.
Macromolecules 2010, 43, 6270-6277.
(42) Zhang, F.; Jonforsen, M.; Johansson, D. M.; Andersson, M.
R.; Inganas, O., Photodiodes and Solar Cells Based on the N-
Type Polymer Poly(Pyridopyrazine Vinylene) as Electron
Acceptor. Synth. Met. 2003, 138, 555-560.
(43) Roncali, J.; Leriche, P.; Blanchard, P., Molecular Materials
for Organic Photovoltaics: Small Is Beautiful. Adv. Mater. 2014,
26, 3821-3838.
(22) Bai, H.; Wang, Y.; Cheng, P.; Li, Y.; Zhu, D.; Zhan, X.,
Acceptor-Donor-Acceptor
Small
Molecules
Based
on
Indacenodithiophene for Efficient Organic Solar Cells. ACS Appl.
Mater. Interfaces 2014, 6, 8426-8433.
(23) Lee, O. P.; Yiu, A. T.; Beaujuge, P. M.; Woo, C. H.;
Holcombe, T. W.; Millstone, J. E.; Douglas, J. D.; Chen, M. S.;
Frechet, J. M., Efficient Small Molecule Bulk Heterojunction
Solar Cells with High Fill Factors Via Pyrene-Directed Molecular
Self-Assembly. Adv. Mater. 2011, 23, 5359-5363.
(24) Sun, K.; Xiao, Z.; Lu, S.; Zajaczkowski, W.; Pisula, W.;
Hanssen, E.; White, J. M.; Williamson, R. M.; Subbiah, J.;
Ouyang, J.; Holmes, A. B.; Wong, W. W.; Jones, D. J., A
Molecular Nematic Liquid Crystalline Material for High-
Performance Organic Photovoltaics. Nat. Commun. 2015, 6, 6013.
(25) Wang, J.-L.; Wu, Z.; Miao, J.-S.; Liu, K.-K.; Chang, Z.-F.;
Zhang, R.-B.; Wu, H.-B.; Cao, Y., Solution-Processed
Diketopyrrolopyrrole-Containing Small-Molecule Organic Solar
Cells with 7.0% Efficiency: In-Depth Investigation on the Effects
of Structure Modification and Solvent Vapor Annealing. Chem.
Mater. 2015, 27, 4338-4348.
(26) Takacs, C. J.; Sun, Y.; Welch, G. C.; Perez, L. A.; Liu, X.;
Wen, W.; Bazan, G. C.; Heeger, A. J., Solar Cell Efficiency, Self-
Assembly, and Dipole-Dipole Interactions of Isomorphic
Narrow-Band-Gap Molecules. J. Am. Chem. Soc. 2012, 134, 16597-
16606.
(27) He, X.; Cao, B.; Hauger, T. C.; Kang, M.; Gusarov, S.; Luber,
E. J.; Buriak, J. M., Donor-Acceptor Small Molecules for Organic
Photovoltaics: Single-Atom Substitution (Se or S). ACS Appl.
Mater. Interfaces 2015, 7, 8188-8199.
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
(28) Patra, D.; Huang, T. Y.; Chiang, C. C.; Maturana, R. O.; Pao,
C. W.; Ho, K. C.; Wei, K. H.; Chu, C. W., 2-Alkyl-5-Thienyl-
Substituted
Benzo[1,2-b:4,5-b']Dithiophene-Based
Donor
Molecules for Solution-Processed Organic Solar Cells. ACS Appl.
Mater. Interfaces 2013, 5, 9494-9500.
(29) Weidelener, M.; Wessendorf, C. D.; Hanisch, J.; Ahlswede,
E.; Gotz, G.; Linden, M.; Schulz, G.; Mena-Osteritz, E.; Mishra,
A.; Bauerle, P., Dithienopyrrole-Based Oligothiophenes for
Solution-Processed Organic Solar Cells. Chem. Commun. 2013,
49, 10865-10867.
(30) Ren, Y.; Hailey, A. K.; Hiszpanski, A. M.; Loo, Y.-L.,
Isoindigo-Containing Molecular Semiconductors: Effect of
Backbone Extension on Molecular Organization and Organic
Solar Cell Performance. Chem. Mater. 2014, 26, 6570-6577.
(31) Price, S. C.; Stuart, A. C.; Yang, L.; Zhou, H.; You, W.,
Fluorine Substituted Conjugated Polymer of Medium Band Gap
Yields 7% Efficiency in Polymer-Fullerene Solar Cells. J. Am.
Chem. Soc. 2011, 133, 4625-4631.
(32) Andersson, M.; Bo, Z.; Liu, Z.; Ingana, O.; Qin, R.; Li, W.; Li,
C.; Du, C.; Veit, C.; Schleiermacher, H.; Wuerfel, U.; Zhang, F., A
Planar Copolymer for High Efficiency Polymer Solar Cells. J. Am.
Chem. Soc. 2009, 131, 14612-14613.
(33) Bouffard, J.; Swager, T., Fluorescent Conjugated Polymers
That Incorporate Substituted
(44) Zhang, X.; Mao, J.; Wang, D.; Li, X.; Yang, J.; Shen, Z.; Wu,
W.; Li, J.; Agren, H.; Hua, J., Comparative Study on Pyrido[3,4-
B]Pyrazine-Based Sensitizers by Tuning Bulky Donors for Dye-
Sensitized Solar Cells. ACS Appl. Mater. Interfaces 2015, 7, 2760-
2771.
(45) Ying, W.; Yang, J.; Wielopolski, M.; Moehl, T.; Moser, J.-E.;
Comte, P.; Hua, J.; Zakeeruddin, S. M.; Tian, H.; Graetzel, M.,
New Pyrido[3,4-b]Pyrazine-Based Sensitizers for Efficient and
Stable Dye-Sensitized Solar Cells. Chem. Sci. 2014, 5, 206-214.
(46) Li, X.; Cui, S.; Wang, D.; Zhou, Y.; Zhou, H.; Hu, Y.; Liu, J.-
g.; Long, Y.; Wu, W.; Hua, J.; Tian, H., New Organic Donor-
Acceptor-Π-Acceptor Sensitizers for Efficient Dye-Sensitized
Solar Cells and Photocatalytic Hydrogen Evolution under
Visible-Light Irradiation. ChemSusChem 2014, 7, 2879-2888.
(47) Shi, Q.; Chen, W.-Q.; Xiang, J.; Duan, X.-M.; Zhan, X., A
Low-Bandgap Conjugated Polymer Based on Squaraine with
Strong Two-Photon Absorption. Macromolecules 2011, 44, 3759-
3765.
(48) Cabanetos, C.; El Labban, A.; Bartelt, J. A.; Douglas, J. D.;
Mateker, W. R.; Frechet, J. M.; McGehee, M. D.; Beaujuge, P. M.,
2,1,3-Benzooxadiazole
and
2,1,3-Benzothiadiazole
Units.
Macromolecules 2008, 41, 5559-5562.
Linear
Side
Chains
in
Benzo[1,2-b:4,5-b']Dithiophene-
(34) Xu, X.; Wang, C.; Bäcke, O.; James, D.; Bini, K.; Olsson, E.;
Andersson, M.; Fahlman, M.; Wang, E., Pyrrolo[3,4-
g]quinoxaline-6,8-dione-based Conjugated Copolymers for Bulk
Heterojunction Solar Cells with High Photovoltages. Polym.
Chem. 2015, 6, 4624-4633.
(35) Tessarolo, M.; Gedefaw, D.; Bolognesi, M.; Liscio, F.;
Henriksson, P.; Zhuang, W.; Milita, S.; Muccini, M.; Wang, E.;
Seri, M.; Andersson, M., Structural Tuning of Quinoxaline-
Thieno[3,4-C]Pyrrole-4,6-Dione Polymers Direct Self-Assembly
and Solar Cell Performance. J. Am. Chem. Soc. 2013, 135, 4656-
4659.
(49) Warnan, J.; Cabanetos, C.; Bude, R.; El Labban, A.; Li, L.;
Beaujuge, P. M., Electron-Deficientn-Alkyloyl Derivatives of
Thieno[3,4-c]Pyrrole-4,6-Dione Yield Efficient Polymer Solar
Cells with Open-Circuit Voltages > 1 V. Chem. Mater. 2014, 26,
2829-2835.
9
ACS Paragon Plus Environment