Curved Perylene Diimides Fused with Seven-Membered Rings.
conformational flexibility
curved π-system
organic photovoltaics
perylene diimide
seven-membered ring
Journal
Chemistry, an Asian journal
ISSN: 1861-471X
Titre abrégé: Chem Asian J
Pays: Germany
ID NLM: 101294643
Informations de publication
Date de publication:
15 Mar 2021
15 Mar 2021
Historique:
received:
21
01
2021
pubmed:
26
1
2021
medline:
26
1
2021
entrez:
25
1
2021
Statut:
ppublish
Résumé
Curved perylene diimides fused with seven-membered rings have been synthesized using a regioselective bay-functionalization method and Pd-catalyzed intramolecular C-H/C-Br coupling reaction. X-Ray analysis and temperature-dependent NMR spectroscopy revealed the curved molecular structure with a certain degree of conformational flexibility. The curved and expanded π-conjugation altered the electronic properties while retaining the intrinsic properties of the parent perylene diimide. Despite the absence of solubilizing N-substituents, the curved perylene diimides showed sufficient solubility for application in solution-processed organic photovoltaic devices. The devices showed superior performance with a power conversion efficiency of up to 2.76% due to suppressed charge recombination. Our detailed investigations suggest that the introduction of a curved structure enables the removal of the bulky N-substituents, which is an effective way to achieve a thin-film morphology suitable for photoelectric conversion.
Identifiants
pubmed: 33491273
doi: 10.1002/asia.202100066
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
690-695Subventions
Organisme : Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan
ID : 18K14115
Organisme : Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan
ID : 19K15536
Organisme : Toukai Foundation for Technology
Organisme : Mazda foundation
Organisme : Kao Foundation for Arts and Sciences
Organisme : Japan Synchrotron Radiation Research Institute (JASRI)
ID : 2020A1627
Informations de copyright
© 2021 Wiley-VCH GmbH.
Références
T. Kawase, H. Kurata, Chem. Rev. 2006, 106, 5250-5273;
M. Rickhaus, M. Mayor, M. Juríček, Chem. Soc. Rev. 2017, 46, 1643-1660.
Y. Shen, C.-F. Chen, Chem. Rev. 2012, 112, 1463-1535;
M. Gingras, Chem. Soc. Rev. 2013, 42, 1051-1095.
P. W. Rabideau, A. Sygula, Acc. Chem. Res. 1996, 29, 235-242;
S. Higashibayashi, H. Sakurai, Chem. Lett. 2011, 40, 122-128.
Y. Segawa, A. Yagi, K. Matsui, K. Itami, Angew. Chem. Int. Ed. 2016, 55, 5136-5158;
Angew. Chem. 2016, 128, 5222-5245;
G. Povie, Y. Segawa, T. Nishihara, Y. Miyauchi, K. Itami, Science 2017, 356, 172-175.
S. H. Pun, Q. Miao, Acc. Chem. Res. 2018, 51, 1630-1642.
M. A. Majewski, M. Stępień, Angew. Chem. Int. Ed. 2019, 58, 86-116;
Angew. Chem. 2019, 131, 90-122.
J. Luo, X. Xu, R. Mao, Q. Miao, J. Am. Chem. Soc. 2012, 134, 13796-13803;
K. Kawasumi, Q. Zhang, Y. Segawa, L. T. Scott, K. Itami, Nat. Chem. 2013, 5, 739-744;
N. Fukui, T. Kim, D. Kim, A. Osuka, J. Am. Chem. Soc. 2017, 139, 9075-9088;
S. H. Pun, Y. Wang, M. Chu, C. K. Chan, Y. Li, Z. Liu, Q. Miao, J. Am. Chem. Soc. 2019, 141, 9680-9686;
S. Hayakawa, A. Kawasaki, Y. Hong, D. Uraguchi, T. Ooi, D. Kim, T. Akutagawa, N. Fukui, H. Shinokubo, J. Am. Chem. Soc. 2019, 141, 19807-19816;
S. Hayakawa, K. Matsuo, H. Yamada, N. Fukui, H. Shinokubo, J. Am. Chem. Soc. 2020, 142, 11663-11668.
T. Amaya, S. Seki, T. Moriuchi, K. Nakamoto, T. Nakata, H. Sakane, A. Saeki, S. Tagawa, T. Hirao, J. Am. Chem. Soc. 2009, 131, 408-409;
Y. Ueda, H. Tsuji, H. Tanaka, E. Nakamura, Chem. Asian J. 2014, 9, 1623-1628;
A. Wakamiya, H. Nishimura, T. Fukushima, F. Suzuki, A. Saeki, S. Seki, I. Osaka, T. Sasamori, M. Murata, Y. Murata, H. Kaji, Angew. Chem. Int. Ed. 2014, 53, 5800-5804;
Angew. Chem. 2014, 120, 5910-5914.
F. Würthner, M. Stolte, Chem. Commun. 2011, 47, 5109-5115;
N. A. Minder, S. Ono, Z. Chen, A. Facchetti, A. F. Morpurgo, Adv. Mater. 2012, 24, 503-508;
Y. Zhao, Y. Guo, Y. Liu, Adv. Mater. 2013, 25, 5372-5391;
F. Würthner, C. R. Saha-Möller, B. Fimmel, S. Ogi, P. Leowanawat, D. Schmidt, Chem. Rev. 2016, 116, 962-1052.
C. Li, H. Wonneberger, Adv. Mater. 2012, 24, 613-636;
G. Zhang, J. Zhao, P. C. Y. Chow, K. Jiang, J. Zhang, Z. Zhu, J. Zhang, F. Huang, H. Yan, Chem. Rev. 2018, 118, 3447-3507;
Y.-Q. Pan, G.-Y. Sun, ChemSusChem 2019, 12, 4570-4600;
K. Fujimoto, M. Takahashi, S. Izawa, M. Hiramoto, Materials 2020, 13, 2148;
J. Wang, X. Zhan, Acc. Chem. Res. 2021, 54, 132-143.
Y. Cai, L. Huo, X. Sun, D. Wei, M. Tang, Y. Sun, Adv. Energy Mater. 2015, 5, 1500032;
A. Nowak-Król, F. Würthner, Org. Chem. Front. 2019, 6, 1272-1318;
K. Fujimoto, S. Izawa, Y. Arikai, S. Sugimoto, H. Oue, T. Inuzuka, N. Uemura, M. Sakamoto, M. Hiramoto, M. Takahashi, ChemPlusChem 2020, 85, 285-293.
V. Coropceanu, J. Cornil, D. A. S. Filho, Y. Olivier, R. Silbey, J.-L. Brédas, Chem. Rev. 2007, 107, 926-952.
R. Mishra, P. Panini, J. Sankar, Org. Lett. 2014, 16, 3994-3997;
L. Đorđević, D. Milano, N. Demitri, D. Bonifazi, Org. Lett. 2020, 22, 4283-4288.
M. Takahashi, K. Asaba, T. T. Lua, T. Inuzuka, N. Uemura, M. Sakamoto, T. Sengoku, H. Yoda, J. Org. Chem. 2018, 83, 624-631.
K. Fujimoto, K. Uchida, M. Nakamura, T. Inuzuka, N. Uemura, M. Sakamoto, M. Takahashi, ChemistrySelect 2020, 5, 15028-15031.
A. Pyo, S. Kim, M. R. Kumar, A. Byeun, M. S. Eomb, M. S. Han, S. Lee, Tetrahedron Lett. 2013, 54, 5207-5210.
P. Osswald, F. Würthner, J. Am. Chem. Soc. 2007, 129, 14319-14326.
H. Langhalss, T. Emming, H. Huber, Spectrochim. Acta, 1988, 44, 1189-1193;
G. T. Rushton, W. G. Burns, J. M. Lavin, Y. S. Chong, P. Pellechia, K. D. Shimizu, J. Chem. Educ. 2007, 84, 1499-1501;
A. Sciutto, A. Berezin, M. L. Cicero, T. Miletić, A. Stopin, D. Bonifazi, J. Org. Chem. 2018, 83, 13787-13798.
F. P. Gasparro, N. H. Kolodny, J. Chem. Educ., 1977, 54, 258-261.
C.-C. Chao, M. Leung, J. Org. Chem. 2005, 70, 4323-4331;
Y. Wang, H. Chen, H. Wu, X. Li, Y. Weng, J. Am. Chem. Soc. 2009, 131, 30-31;
R. K. Dubey, A. Efimov, H. Lemmetyinen, Chem. Mater. 2011, 23, 778-788.
D. Shukla, P. Wan, J. Am. Chem. Soc. 1993, 115, 2990-2991.
K. Schmidt, S. Brovelli, V. Coropceanu, D. Beljonne, J. Cornil, C. Bazzini, T. Caronna, R. Tubino, F. Meinardi, Z. Shuai, J.-L. Brédas, J. Phys. Chem. A 2007, 111, 10490-10499;
K. Nagarajan, A. R. Mallia, V. S. Reddy, M. Hariharan, J. Phys. Chem. C 2016, 120, 8443-8450;
K. Nagarajan, A. R. Mallia, K. Muraleedharan, M. Hariharan, Chem. Sci. 2017, 8, 1776-1782.
J. C. S. Costa, R. J. S. Taveira, C. F. R. A. C. Lima, A. Mendes, L. M. N. B. F. Santos, Opt. Mater. 2016, 58, 51-60.
P. Schilinsky, C. Waldauf, C. J. Brabec, Appl. Phys. Lett. 2002, 81, 3885-3887.
S. Izawa, N. Shintaku, M. Kikuchi, M. Hiramoto, Appl. Phys. Lett. 2019, 115, 153301.