Citation: | Siyu Ji, Xuhui Jin. A New Class of Biodegradable Organic Optoelectronic Materials: α-Oligofurans[J].JOURNAL OF BEIJING INSTITUTE OF TECHNOLOGY, 2022, 31(3): 251-258.doi:10.15918/j.jbit1004-0579.2022.014 |
[1] |
G. Zhang, J. Zhao, P. C. Y. Chow, K. Jiang, J. Zhang, Z. Zhu, J. Zhang, F. Huang, and H. Yan, “Nonfullerene acceptor molecules for bulk heterojunction organic solar cells, ”
Chemical Review, vol. 118 , no. 7, pp. 3447-3507, 2018.
|
[2] |
Y. Lin, Y. Li, and X. Zhan, “Small molecule semiconductors for high-efficiency organic photovoltaics, ”
Chemical Society Reviews, vol. 41, no. 11, pp. 4245-4272, 2012.
|
[3] |
Y. Zhao, Y. Guo, and Y. Liu, “25th anniversary article: Recent advances in n-type and ambipolar organic field-effect transistors, ”
Advanced Material, vol. 25, no. 38, pp. 5372-91, 2013.
|
[4] |
Y. Huang, D. L. Elder, A. L. Kwiram, S. A. Jenekhe, A. K. Y. Jen, L. R. Dalton, and C. K. Luscombe, “Organic semiconductors at the University of Washington: Advancements in materials design and synthesis and toward industrial scale production, ”
Advanced Material, vol. 33, no. 22, pp. 1904239, 2013.
|
[5] |
S. Reineke, F. Lindner, G. Schwartz, N. Seidler, K. Walzer, B. Lussem, and K. Leo, “White organic light-emitting diodes with fluorescent tube efficiency, ”
Nature, vol. 459, no. 7244, pp. 234-238, 2009.
|
[6] |
L. Groenendaal, F. Jonas, D. Freitag, H. Pielartzik, and J. R. Reynolds, “Poly(3, 4-ethylenedioxythiophene) and its derivatives: Past, present, and future, ”
Nature, vol. 12 , no. 7, pp. 481-494, 2000.
|
[7] |
W. U. Huynh, J. J. Dittmer, and A. P. Alivisatos, “Hybrid nanorod-polymer solar cells, ”
Science, vol. 295, no. 5564, pp. 2425-2427, 2002.
|
[8] |
Z. Batool, D. Xu, X. Zhang, X. Li, Y. Li, Z. Chen, B. Li, and L. Li, “A review on furan: Formation, analysis, occurrence, carcinogenicity, genotoxicity and reduction methods, ”
Critical Reviews in Food Science and Nutrition, vol. 61, no. 3, pp. 395-406, 2021.
|
[9] |
H. Limpricht, “Ueber das Tetraphenol C4H4O, ”
Januar–Juni, vol. 3, no. 1, pp. 90-91, 1870.
|
[10] |
O. Gidron and M. Bendikov, “α-Oligofurans: An emerging class of conjugated oligomers for organic electronics, ”
Angewandte Chemie International Edition, vol. 53, no. 10, pp. 2546-55, 2014.
|
[11] |
H. Cao and P. A. Rupar, “Recent advances in conjugated furans, ”
Chemistry, vol. 23, no. 59, pp. 14670-14675, 2017.
|
[12] |
A. Gandini, “The irruption of polymers from renewable resources on the scene of macromolecular science and technology, ”
Green Chemistry, vol. 13, no. 5, pp. 1061-1083, 2011.
|
[13] |
H. Tsuji and E. Nakamura, “Design and functions of semiconducting fused polycyclic furans for optoelectronic applications, ”
Accounts of Chemical Research, vol. 50, no. 2, pp. 396-406, 2017.
|
[14] |
B. Zheng and L. J. Huo, “Recent advances of furan and its derivatives based semiconductor materials for organic photovoltaics, ”
Small Methods, vol. 5, no. 9, pp. 2100493, 2021.
|
[15] |
O. Gidron, Y. Diskin-Posner, and M. Bendikov, “α-Oligofurans, ”
Journal of the American Chemical Society, vol. 132, pp. 2148-2150, 2010.
|
[16] |
P. Huang, J. Du, M. C. Biewer, and M. C. Stefan, “Developments of furan and benzodifuran semiconductors for organic photovoltaics, ”
J
ournal of Materials Chemistry A, vol. 3, no. 12, pp. 6244-6257, 2015.
|
[17] |
Y. Liu, J. Yuan, Y. Zou, and Y. Li, “Research progress of the furan containing fused ring conjugated organic molecules and polymers, ”
Acta Chimica Sinica, vol. 75, no. 3, pp. 257-270, 2017.
|
[18] |
U. H. Bunz, “α-Oligofurans: Molecules without a twist, ”
Angewandte Chemie International Edition, vol. 49, no. 30, pp. 5037-5040, 2010.
|
[19] |
S. Sharma and M. Bendikov, “α-Oligofurans: A computational study, ”
Chemistry, vol. 19, no. 39, pp. 13127-13139, 2013.
|
[20] |
Y. Xiong, J. Tao, R. Wang, X. Qiao, X. Yang, D. Wang, H. Wu, and H. Li, “A furan-thiophene-based quinoidal compound: A new class of solution-processable high-performance n-type organic semiconductor, ”
Advanced Material, vol. 28, no. 28, pp. 5949-5953, 2016.
|
[21] |
D. Sheberla, S. Patra, Y. H. Wijsboom, S. Sharma, Y. Sheynin, A. E. Haj-Yahia, A. H. Barak, O. Gidron, and M. Bendikov, “Conducting polyfurans by electropolymerization of oligofurans, ”
Chemical Science, vol. 6, no. 1, pp. 360-371, 2015.
|
[22] |
A. J. Varni, M. Kawakami, S. A. Tristram-Nagle, D. Yaron, T. Kowalewski, and K. J. T. Noonan, “Design, synthesis, and properties of a six-membered oligofuran macrocycle, ”
Organic Chemistry Frontiers, vol. 8, no. 8, pp. 1775-1782, 2021.
|
[23] |
S. V. Mulay, O. Dishi, Y. Fang, M. R. Niazi, L. J. W. Shimon, D. F. Perepichka, and O. Gidron, “A macrocyclic oligofuran: Synthesis, solid state structure and electronic properties, ”
Chemical Science, vol. 10, no. 37, pp. 8527-8532, 2019.
|
[24] |
O. Dishi and O. Gidron, “Macrocyclic oligofurans: A computational study, ”
Journal of Organic Chemistry, vol. 83, no . 6, pp. 3119-3125, 2018.
|
[25] |
X. H. Jin, D. Sheberla, L. J. Shimon, and M. Bendikov, “Highly coplanar very long oligo (alkylfuran)s: A conjugated system with specific head-to-head defect, ”
Journal of the American Chemical Society, vol. 136, no. 6, pp. 2592-2601, 2014.
|
[26] |
O. Gidron, A. Dadvand, E. Wei-Hsin Sun, I. Chung, L. J. W. Shimon, M. Bendikov, and D. F. Perepichka, “Oligofuran-containing molecules for organic electronics, ”
Journal of Materials Chemistry C, vol. 1, no. 28, pp. 4358-4367, 2013.
|
[27] |
L. Fritze, M. Fest, A. Helbig, T. Bischof, I. Krummenacher, H. Braunschweig, M. Finze, and H. Helten, “Boron-doped α-oligo- and polyfurans: Highly luminescent hybrid materials, color-tunable through the doping density, ”
Macromolecules, vol. 54, no. 16, pp. 7653-7665, 2021.
|
[28] |
X. Yin, F. Guo, R. A. Lalancette, and F. Jäkle, “Luminescent main-chain organoborane polymers: highly robust, electron-deficient poly (oligothiophene borane)s via stille coupling polymerization, ”
Macromolecules, vol. 49, no. 2, pp. 537-546, 2016.
|
[29] |
B. Li, “Furan derivatives: An emerging class of organic semiconductors, ”
Chinese Journal of Organic Chemistry, vol. 35, no. 12, pp. 2487-2560, 2015.
|
[30] |
O. Gidron, N. Varsano, L. J. W. Shimon, G. Leitus, and M. Bendikov, “Study of a bifuran vs. bithiophene unit for the rational design of pi-conjugated systems. What have we learned?, ”
Chemical Communications, vol. 49, no. 56, pp. 6256-6258, 2013.
|
[31] |
C. H. Woo, P. M. Beaujuge , T. W. Holcombe, O. P. Lee, and J. M. J. Fréchet, “Incorporation of furan into low band-gap polymers for efficient solar cells, ”
Journal of the American Chemical Society, vol. 132, pp. 15547-15549, 2010.
|
[32] |
E. E. Korshin, G. M. Leitus, and M. Bendikov, “Convenient access to readily soluble symmetrical dialkyl-substituted alpha-oligofurans, ”
Organic & Biomolecular Chemistry, vol. 12, no. 34, pp. 6661-6671, 2014
|
[33] |
H. Liang, X. Zhang, R. Peng, X. Ouyang, Z. Liu, S. Chen, and Z. Ge, “Photovoltaic performance enhancement from diketopyrrolopyrrole-based solar cells through structure manipulation, ”
Dyes and Pigments, vol. 112, pp. 145-153, 2015.
|
[34] |
K. Qian, C. Qu, X. Ma, H. Chen, M. Kandawa-Schulz, W. Song, W. Miao, Y. Wang, and Z. Cheng, “Tuning the near infrared II emitting wavelength of small molecule dyes by single atom alteration, ”
Chemical Communications, vol. 56, no. 4, pp. 523-526, 2020.
|
[35] |
Z. Zhao, H. Nie, C. Ge, Y. Cai, Y. Xiong, J. Qi, W. Wu, R. T. K. Kwok, X. Gao, A. Qin, J. W. Y. Lam, and B. Z. Tang, “Furan is superior to thiophene: A furan-cored AIEgen with remarkable chromism and OLED performance, ”
Advanced Science, vol. 4, no. 8, pp. 1700005, 2017.
|
[36] |
J. T. Henssler and A. J. Matzger, “Regiochemical effects of furan substitution on the electronic properties and solid-state structure of partial fused-ring oligothiophenes, ”
Journal of Organic Chemistry, vol. 77, no. 20, pp. 9298-303, 2012.
|
[37] |
D. Qian, B. Liu, S. Wang, S. Himmelberger, M. Linares, M. Vagin, C. Müller, Z. Ma, S. Fabiano, M. Berggren, A. Salleo, O. Inganäs, Y. Zou, and F. Zhang, “Modulating molecular aggregation by facile heteroatom substitution of diketopyrrolopyrrole based small molecules for efficient organic solar cells, ”
Journal of Materials Chemistry A, vol. 3, no. 48, pp. 24349-24357, 2015.
|
[38] |
C. Capel Ferron, M. C. Ruiz Delgado, O. Gidron, S. Sharma, D. Sheberla, Y. Sheynin, M. Bendikov, J. T. Lopez Navarrete, and V. Hernandez, “alpha-Oligofurans show a sizeable extent of pi-conjugation as probed by Raman spectroscopy, ”
Chemical Communication, vol. 48, no. 53, pp. 6732-6734, 2012.
|
[39] |
O. Gidron, Y. Diskin-Posner, and M. Bendikov, “High charge delocalization and conjugation in oligofuran molecular wires, ”
Chemistry, vol. 19, no. 39, pp. 13140-13150, 2013.
|
[40] |
S. Gadakh, L. J. W. Shimon, and O. Gidron, “Regioselective transformation of long pi-conjugated backbones: From oligofurans to oligoarenes, ”
Angewandte Chemie International Edition, vol. 56, no. 44, pp. 13601-13605, 2017.
|
[41] |
Y. Chen, P. Shen, T. Cao, H. Chen, Z. Zhao, and S. Zhu, “Bottom-up modular synthesis of well-defined oligo(arylfuran)s, ”
Nature Communication, vol. 12 no. 1, pp. 6165-6177, 2021.
|