Regioselective Bay-Functionalization of Perylenes Toward Tailor-Made Synthesis of Acceptor Materials for Organic Photovoltaics.
bromination
nonfullerene acceptors
organic photovoltaics
perylene
voltage loss
Journal
ChemPlusChem
ISSN: 2192-6506
Titre abrégé: Chempluschem
Pays: Germany
ID NLM: 101580948
Informations de publication
Date de publication:
Feb 2020
Feb 2020
Historique:
received:
10
12
2019
revised:
21
01
2020
pubmed:
23
1
2020
medline:
23
1
2020
entrez:
23
1
2020
Statut:
ppublish
Résumé
The development of an efficient synthetic protocol for multiply bay-functionalized perylenes and application of these products to photovoltaics are reported. Tetrabenzyl 1-(4-tert-butylphenoxy)perylene-3,4,9,10-tetracarboxylate underwent a regioselective bromination at the 7-position followed by a further bromination at the 12-position to provide a 7,12-dibromide in high 84% yield. This compound was transformed into a tetrasubstituted C
Identifiants
pubmed: 31967408
doi: 10.1002/cplu.201900725
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
285-293Subventions
Organisme : Nanotechnology Platform Program (Molecule and Material Synthesis)
Organisme : JSPS KAKENHI
ID : 18K14115
Organisme : Ministery of Education, Culture, Sports, Science and Technology (MEXT), Japan
Organisme : Ogasawara Foundation for the Promotion of Science & Engineering
Organisme : Takahashi Industrial and Economic Research Foundation
Organisme : Foundation of Chubu Science and Technology Center
Organisme : Mazda Foundation
Informations de copyright
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Références
C. W. Tang, Appl. Phys. Lett. 1986, 48, 183-185.
M. Hiramoto, H. Fujiwara, M. Yokoyama, Appl. Phys. Lett. 1991, 58, 1062-1064.
G. Yu, J. Gao, J. C. Hummelen, F. Wudl, A. J. Heeger, Science 1995, 270, 1789-1791.
J. E. Coughlin, Z. B. Henson, G. C. Welch, G. C. Bazan, Acc. Chem. Res. 2014, 47, 257-270.
W. Jiang, Y. Li, Z. Wang, Acc. Chem. Res. 2014, 47, 3135-3147.
N. A. Minder, S. Ono, Z. Chen, A. Facchetti, A. F. Morpurgo, Adv. Mater. 2012, 24, 503-508.
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.
R. K. Dubey, S. J. Eustace, J. S. van Mullem, E. J. R. Sudhölter, F. C. Grozema, W. F. Jager, J. Org. Chem. 2019, 84, 9532-9547.
M. Takahashi, K. Asaba, T. T. Lua, T. Inuzuka, N. Uemura, M. Sakamoto, T. Sengoku, H. Yoda, J. Org. Chem. 2018, 83, 624-631.
M. Takahashi, Y. Suzuki, Y. Ichihashi, M. Yamashita, H. Kawai, Tetrahedron Lett. 2007, 48, 357-359.
S. Izawa, N. Shintaku, M. Kikuchi, M. Hiramoto, Appl. Phys. Lett. 2019, 115, 153301.
X. Zhang, C. Zhan, X. Zhang, J. Yao, Tetrahedron 2013, 69, 8155-8160.
K. Khokhlov, N. J. Schuster, F. Ng, C. Nuckolls, Org. Lett. 2018, 20, 1991-1994.
L. Perrin, P. Hudhomme, Eur. J. Org. Chem. 2011, 5427-5440.
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.
D. Qian, Z. Zheng, H. Yao, W. Tress, T. R. Hopper, S. Chen, S. Li, J. Liu, S. Chen, J. Zhang, X.-K. Liu, B. Gao, L. Ouyang, Y. Jin, G. Pozina, I. A. Buyanova, W. M. Chen, O. Inganäs, V. Coropceanu, J.-L. Bredas, H. Yan, J. Hou, F. Zhang, A. A. Bakulin, F. Gao, Nat. Mater. 2018, 17, 703-709.
P. Schilinsky, C. Waldauf, C. J. Brabec, Appl. Phys. Lett. 2002, 81, 3885-3887.
K. Vandewal, K. Tvingstedt, A. Gadisa, O. Inganas, J. V. Manca, Phys. Rev. B 2010, 81, 125204.
J. Liu, S. Chen, D. Qian, B. Gautam, G. Yang, J. Zhao, J. Bergqvist, F. Zhang, W. Ma, H. Ade, O. Inganäs, K. Gundogdu, F. Gao, H. Yan, Nat. Energy 2016, 1, 16089.
D. Magde, R. Wong, P. G. Seybold, Photochem. Photobiol. 2002, 75, 327-334.