Abstract
We reported two tetraphenylpyrrolo[3,2‐b]pyrroles in which the central core is functionalized by electron-rich functions: methoxy and di(4-methoxyphenyl)aminyl. The targeted compounds have good solubility in common organic solvents, high thermal stability and glass forming capacity. The optical and electrochemical properties of these compounds suggest use in a diverse range of applications. When utilized as the hole transporting layer of the planar perovskite solar cells, power conversion efficiencies ranging from 12.8 to 14.5% were obtained.
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References
B. Kan, Y. Kan, L. Zuo, X. Shi, K. Gao, InfoMat 3, 175–200 (2021)
C.C. Lee, R. Estrada, Y.Z. Li, S. Biring, N.R. Al Amin, M.Z. Li, S.W. Liu, K.T. Wong, Adv. Opt. Mater. 8, 2000519 (2020)
J.M. Ha, S.H. Hur, A. Pathak, J.E. Jeong, H.Y. Woo, NPG Asia Mater. 13, 1–36 (2021)
X. Yin, Z. Song, Z. Li, W. Tang, Energy Environ. Sci. 13, 4057–4086 (2020)
Y. Wang, Y. Yue, X. Yang, L. Han, Adv. Energy Mater. 8, 1800249 (2018)
R. Singh, P.K. Singh, B. Bhattacharya, H.W. Rhee, Appl. Mater. Today 14, 175–200 (2019)
M. Krzeszewski, D. Gryko, D.T. Gryko, Acc. Chem. Res. 50, 2334–2345 (2017)
A. Janiga, E. Glodkowska-Mrowka, T. Stoklosa, D.T. Gryko, Asian. J. Org. Chem. 2, 411–415 (2013)
M. Krzeszewski, M. Tasior, M. Grzybowski, D.T. Gryko, Org. Synth. 98, 242–262 (2021)
M. Tasior, O. Vakuliuk, D. Koga, B. Koszarna, K. Górski, M. Grzybowski, Ł Kielesiński, M. Krzeszewski, D.T. Gryko, J. Org. Chem. 85, 13529–13543 (2020)
M. Tasior, P. Kowalczyk, M. Przybył, M. Czichy, P. Janasik, M.H.E. Bousquet, M. Łapkowski, M. Rammo, A. Rebane, D. Jacquemin, D.T. Gryko, Chem. Sci. 12, 15935–15946 (2021)
Y.M. Poronik, L.M. Mazur, M. Samoć, D. Jacquemin, D.T. Gryko, J. Mater. Chem. C 5, 2620–2628 (2017)
C.S. Hawes, G.M.O. Mille, K. Byrne, W. Schmitt, T. Gunnlaugsson, Dalt. Trans. 47, 10080–10092 (2018)
L.M. Martins, B.A. Bregadiolli, L.C. Augusto, J.H.L. De Carvalho, M.A. Zaghete, L.C. Da Silva Filho, Mater. Res. 24, 20210008 (2021)
R. Domínguez, N.F. Montcada, P. de la Cruz, E. Palomares, F. Langa, ChemPlusChem 82, 1096–1104 (2017)
L.S. Duan, Q.P. Wu, Y.Y. Xu, H. Wang, Z. Sun, Y. Chen, S. Xue, Chinese. J. Chem. Phys. 34, 217 (2021)
J. Keruckas, R. Lygaitis, J. Simokaitiene, J.V. Grazulevicius, V. Jankauskas, G. Sini, J. Mater. Chem. 22, 3015–3027 (2012)
L.M. Martins, S. de Faria Vieira, G.B. Baldacim, B.A. Bregadiolli, J.C. Caraschi, A. Batagin-Neto, L.C. da Silva-Filho, Dye. Pigment. 148, 81–90 (2018)
C.M. Cardona, W. Li, A.E. Kaifer, D. Stockdale, G.C. Bazan, Adv. Mater. 23, 2367–2371 (2011)
T.H. Le, Q.-D. Dao, M.-P. Nghiêm, S. Péralta, R. Guillot, Q.N. Pham, A. Fujii, M. Ozaki, F. Goubard, T.-T. Bui, Chem. Asian J. 13, 1302–1311 (2018)
W.J. Kim, Y. Nishikawa, T.T. Bui, F. Goubard, Q.D. Dao, A. Fujii, M. Ozaki, Jpn. J. Appl. Phys. 59, SGGG01 (2020)
Y. Nakamura, T. Nakazato, T. Kamatsuka, H. Shinokubo, Y. Miyake, Chem. Eur. J. 25, 10571–10574 (2019)
P.C. Purba, S. Bhattacharyya, M. Maity, S. Mukhopadhyay, P. Howlader, P.S. Mukherjee, Chem. Commun. 55, 8309–8312 (2019)
Acknowledgements
The work at CY Cergy Paris Université is funded by French National Research Agency (Agence Nationale de la Recherche, ANR) through two projects: ESPOIR2 ANR JCJC (ANR-17-CE05-0006) and FUTUR—CY Initiative of Excellence (ANR-16-IDEX-0008).
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Materials syntheses were formed by Thanh-Tung Dang. Thermal, Optical, and Electrochemical data were collected by Thanh-Tuân Bui. Photovoltaic data collection and analysis were performed by Michael Spence and Suzanne K. Thomas. Thanh-Tuân Bui and Matthew Carnie designed and supervised the study. The first draft of the manuscript was written by Thanh-Tuan Bui and all authors commented on previous versions of the manuscript. All authors read and approved the final manuscript.
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Dang, TT., Spence, M., Thomas, S.K. et al. Tetraphenylpyrrolo[3,2‐b]pyrroles: Synthesis, Thermal, Optical, Electrochemical Properties and Photovoltaic Applications. J Mater Sci: Mater Electron 33, 17773–17779 (2022). https://doi.org/10.1007/s10854-022-08639-2
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DOI: https://doi.org/10.1007/s10854-022-08639-2