Naphthodithiophene-based donor materials for solution processed organic solar cells
- Corresponding author: Kun Lu, luk@nanoctr.cn Zhi-Xiang Wei, weizx@nanoctr.cn
Citation: Xiang-Wei Zhu, Kun Lu, Huan Li, Rui-Min Zhou, Zhi-Xiang Wei. Naphthodithiophene-based donor materials for solution processed organic solar cells[J]. Chinese Chemical Letters, ;2016, 27(8): 1271-1276. doi: 10.1016/j.cclet.2016.06.015
S. Shinamura, I. Osaka, E. Miyazaki. Linear-and angular-shaped naphthodithiophenes: selective synthesis, properties, and application to organic fieldeffect transistors[J]. J. Am. Chem. Soc., 2011,133:5024-5035. doi: 10.1021/ja110973m
S. Shinamura, E. Miyazaki, K. Takimiya. Synthesis, properties, crystal structures, and semiconductor characteristics of naphtho[J]. J. Org. Chem., 2010,75:1228-1234. doi: 10.1021/jo902545a
I. Osaka, T. Abe, S. Shinamura, E. Miyazaki, K. Takimiya. High-mobility semiconducting naphthodithiophene copolymers[J]. J. Am. Chem. Soc., 2010,132:5000-5001. doi: 10.1021/ja101125p
I. Osaka, T. Abe, S. Shinamura, K. Takimiya. Impact of isomeric structures on transistor performances in naphthodithiophene semiconducting polymers[J]. J. Am. Chem. Soc., 2011,133:6852-6860. doi: 10.1021/ja201591a
J.H. Hou, M.H. Park, S.Q. Zhang. Bandgap and molecular energy level control of conjugated polymer photovoltaic materials based on benzo[J]. Macromolecules, 2008,41:6012-6018. doi: 10.1021/ma800820r
. Loser, C.J. Bruns, H. Miyauchi. A naphthodithiophene-diketopyrrolopyrrole donor molecule for efficient solution-processed solar cells[J]. J. Am. Chem. Soc, 2011,133:8142-8145. doi: 10.1021/ja202791n
P. Dutta, W. Yang, S.H. Eom. Development of naphtho[J]. Chem. Commun., 2012,48:573-575. doi: 10.1039/C1CC15465F
P. Dutta, W. Yang, W.H. Lee, I.N. Kang, S.H. Lee. Lee, Novel naphtho[1, 2-b:5, 6-b'] dithiophene core linear donor-π-acceptor conjugated small molecules with thiophene-bridged bithiazole acceptor: design, synthesis, and their application in bulk heterojunction organic solar cells[J]. J. Mater. Chem., 2012,22:10840-10851. doi: 10.1039/c2jm30934c
S. Loser, H. Miyauchi, J.W. Hennek. A "zig-zag" naphthodithiophene core for increased efficiency in solution-processed small molecule solar cells[J]. Chem. Commun, 2011,48:8511-8513.
X.W. Zhu, B.Z. Xia, K. Lu. Naphtho[J]. Chem. Mater., 2016,28:943-950. doi: 10.1021/acs.chemmater.5b04668
D. Deng, Y.J. Zhang, L. Yuan. Effects of shortened alkyl chains on solutionprocessable small molecules with oxo-alkylated nitrile end-capped acceptors for high-performance organic solar cells[J]. Adv. Energy Mater., 2014,41400538. doi: 10.1002/aenm.201400538
Q. Peng, Q. Huang, X.B. Hou. Enhanced solar cell performance by replacing benzodithiophene with naphthodithiophene in diketopyrrolopyrrole-based copolymers[J]. Chem. Commun., 2012,48:11452-11454. doi: 10.1039/c2cc36324k
K. Li, Z.J. Li, K. Feng. Development of large band-gap conjugated copolymers for efficient regular single and tandem organic solar cells[J]. J. Am. Chem. Soc., 2013,135:13549-13557. doi: 10.1021/ja406220a
S. Sanjaykumar, C.E. Song, W.S. Shin. Synthesis and characterization of a novel naphthodithiophene-based copolymer for use in polymer solar cells[J]. Macromolecules, 2012,45:6938-6945. doi: 10.1021/ma301312d
R.S. Koti, S.R. Sanjaykumar, S.J. Hong. 3, 8-Dialkoxynaphthodithiophene based copolymers for efficient polymer solar cell[J]. Sol. Energy Mater. Sol. Cells, 2013,108:213-222. doi: 10.1016/j.solmat.2012.09.021
P. Dutta, H. Park, W.H. Lee. Synthesis characterization and bulk-heterojunction photovoltaic applications of new naphtho[J]. Polym. Chem., 2014,5:132-143. doi: 10.1039/C3PY00911D
P. Dutta, H. Park, M. Oh. Modulation of electronic properties of π-conjugated copolymers derived from naphtho[J]. J. Polym. Sci. Part A: Polym. Chem., 2013,51:2948-2958. doi: 10.1002/pola.26691
I. Osaka, T. Abe, M. Shimawaki, T. Koganezawa, K. Takimiya. Naphthodithiophenebased donor-acceptor polymers: versatile semiconductors for OFETs and OPVs[J]. ACS Macro Lett., 2012,1:437-440. doi: 10.1021/mz300065t
C. Bathula, S. Badgujar, C.E. Song. Effect of backbone structures on photovoltaic properties in naphthodithiophene-based copolymers[J]. J. Polym. Sci. Part A: Polym. Chem., 2014,52:305-312. doi: 10.1002/pola.27005
C. Bathula, C.E. Song, S. Badgujar. Naphtho[J]. Polym. Chem., 2013,4:2132-2139. doi: 10.1039/c3py21062f
S.W. Shi, P. Jiang, S.Q. Yu. Efficient polymer solar cells based on a broad bandgap D-A copolymer of "zigzag" naphthodithiophene and thieno[J]. J. Mater. Chem. A, 2013,1:1540-1543. doi: 10.1039/C2TA01143C
S.W. Shi, X.D. Xie, P. Jiang. Naphtho[J]. Macromolecules, 2013,46:3358-3366. doi: 10.1021/ma400177w
J. Lee, H. Ko, E. Song. Naphthodithiophene-based conjugated polymer with linear, planar backbone conformation and strong intermolecular packing for efficient organic solar cells[J]. ACS Appl. Mater. Interfaces, 2015,7:21159-21169. doi: 10.1021/acsami.5b04884
S.W. Cheng, C.E. Tsai, W.W. Liang. Angular-shaped 4, 9-dialkylnaphthodithiophene-based donor-acceptor copolymers for efficient polymer solar cells and high-mobility field-effect transistors[J]. Macromolecules, 2015,48:2030-2038. doi: 10.1021/acs.macromol.5b00098
S.W. Cheng, D.Y. Chiou, C.E. Tsai. Angular-shaped 4, 9-dialkyl a-and bnaphthodithiophene-based donor-acceptor copolymers: investigation of isomeric structural effects on molecular properties and performance of field-effect transistors and photovoltaics[J]. Adv. Funct. Mater., 2015,25:6131-6143. doi: 10.1002/adfm.v25.38
S.W. Cheng, D.Y. Chiou, Y.Y. Lai. Synthesis and molecular properties of four isomeric dialkylated angular-shaped naphthodithiophenes[J]. Org. Lett., 2013,15:5338-5341. doi: 10.1021/ol4025953
S. Shinamura, R. Sugimoto, N. Yanai. Orthogonally functionalized naphthodithiophenes: selective protection and borylation[J]. Org. Lett., 2012,14:4718-4721. doi: 10.1021/ol301797g
I. Osaka, T. Kakara, N. Takemura, T. Koganezawa, K. Takimiya. Naphthodithiophene-naphthobisthiadiazole copolymers for solar cells: alkylation drives the polymer backbone flat and promotes efficiency[J]. J. Am. Chem. Soc., 2013,135:8834-8837. doi: 10.1021/ja404064m
L.J. Huo, J.H. Hou, S.Q. Zhang, H.Y. Chen, Y. Yang. A polybenzo[1, 2-b:4, 5-b'] dithiophene derivative with deep HOMO level and its application in highperformance polymer solar cells[J]. Angew. Chem. Int. Ed, 2010,49:1500-1503. doi: 10.1002/anie.200906934
L.J. Huo, S.Q. Zhang, X. Guo. Replacing alkoxy groups with alkylthienyl groups: a feasible approach to improve the properties of photovoltaic polymers[J]. Angew. Chem. Int. Ed., 2011,50:9697-9702. doi: 10.1002/anie.201103313
S.W. Shi, K.L. Shi, R. Qu. Alkylphenyl substituted naphthodithiophene: a new building unit with conjugated side chains for semiconducting materials[J]. Macromol. Rapid Commun., 2014,35:1886-1889.
X.W. Zhu, J. Fang, K. Lu. Naphtho[J]. Chem. Mater., 2014,26:6947-6954. doi: 10.1021/cm5033223
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