Preparation of Naphthalene Dianhydride Bithiophene Copolymers by Direct Arylation Polycondensation and the Latent Pigment Approach.
materials science
polymerization
semiconductors
thermochemistry
voltammetry
Journal
ChemPlusChem
ISSN: 2192-6506
Titre abrégé: Chempluschem
Pays: Germany
ID NLM: 101580948
Informations de publication
Date de publication:
Sep 2019
Sep 2019
Historique:
received:
02
04
2019
revised:
20
05
2019
entrez:
17
1
2020
pubmed:
17
1
2020
medline:
17
1
2020
Statut:
ppublish
Résumé
An alternating naphthalene dianhydride bithiophene copolymer (PNDAT2) is prepared by a combined direct arylation polycondensation and the latent pigment approach. PNDAT2 is the first reported example of an alternating conjugated polymer containing naphthalene dianhydride, the oxo-analogue of naphthalene diimide often used in electron-acceptor conjugated polymers. PNDAT2 is resistant to organic solvents and can be generated directly as film by thermal treatment of the soluble tetraester precursor PNTET2. PNDAT2 is characterized by a LUMO level of -3.9 eV, similar to that of established naphthalene diimide containing soluble copolymers. This route to insoluble electron acceptor copolymers by thermal cleavage of soluble precursors is an alternative to classical cross-linking or orthogonal processing strategies.
Identifiants
pubmed: 31944044
doi: 10.1002/cplu.201900210
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
1346-1352Subventions
Organisme : Italian Ministry of University and Re- search (MIUR)
Organisme : PRIN2017 BOOSTER
ID : 2017YXX8AZ
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Références
M. Caironi, Y.-Y.Noh Large Area and Flexible Electronics, Wiley-VCH, Weinheim, 2015.
R. Turrisi, L. Mascheroni, M. Sassi, M. Rooney, N. Buccheri, R. Ruffo, A. Facchetti, L. Beverina, Eur. J. Org. Chem. 2016, 23, 4032-4040.
M. H. Hoang, D. N. Nguyen, D. H. Choi, Adv. Nat. Sci: Nanosci. Nanotechnol. 2011, 2, 045006.
H. J. Kim, A.-R. Han, C.-H. Cho, H. Kang, H.-H. Cho, M. Y. Lee, J. M. J. Fréchet, J. H. Oh, B. J. Kim, Chem. Mater. 2012, 24, 215-221.
X. Chen, L. Chen, Y. Chen, J. Polym. Sci. Polym. Chem. Ed. 2013, 51, 4156-4166.
G. Griffini, J. D. Douglas, C. Piliego, T. W. Holcombe, S. Turri, J. M. J. Fréchet, J. L. Mynar, Adv. Mater. 2011, 23, 1660-1664.
R.-Q. Png, P.-J. Chia, J.-C. Tang, B. Liu, S. Sivaramakrishnan, M. Zhou, S.-H. Khong, H. S. O. Chan, J. H. Burroughes, L.-L. Chua, R. H. Friend, P. K. H. Ho, Nat. Mater. 2009, 9, 152-158.
J. Zambounis, Z. Hao, A. Iqbal, Nature 1997, 388, 131-132.
J. Liu, E. N. Kadnikova, Y. Liu, M. D. McGehee, J. M. J. Fréchet, J. Am. Chem. Soc. 2004, 126, 9486-9487.
C. Edder, P. B. Armstrong, K. B. Prado, J. M. J. Fréchet, Chem. Commun. 2006, 1965-1967.
M. Helgesen, S. A. Gevorgyan, F. C. Krebs, R. A. J. Janssen, Chem. Mater. 2009, 21, 4669-4675.
M. H. Petersen, S. A. Gevorgyan, F. C. Krebs, Macromolecules 2008, 41, 8986-8994.
O. Fenwick, L. Bozec, D. Credgington, A. Hammiche, G. M. Lazzerini, Y. R. Silberberg, F. Cacialli, Nature Nanotech 2009, 4, 664-668.
B. Sun, W. Hong, H. Aziz, Y. Li, J. Mater. Chem. 2012, 22, 18950.
E. D. Głowacki, G. Voss, K. Demirak, M. Havlicek, N. Sünger, A. C. Okur, U. Monkowius, J. Ga̧siorowski, L. Leonat, N. S. Sariciftci, Chem. Commun. 2013, 49, 6063.
T.-H. Liu, W.-T. Cheng, K.-T. Huang, Ind. Eng. Chem. Res. 2010, 49, 541-547.
M. Sytnyk, E. D. Głowacki, S. Yakunin, G. Voss, W. Schöfberger, D. Kriegner, J. Stangl, R. Trotta, C. Gollner, S. Tollabimazraehno, G. Romanazzi, Z. Bozkurt, M. Havlicek, N. S. Sariciftci, W. Heiss, J. Am. Chem. Soc. 2014, 136, 16522-16532.
E. D. Głowacki, H. Coskun, M. A. Blood-Forsythe, U. Monkowius, L. Leonat, M. Grzybowski, D. Gryko, M. S. White, A. Aspuru-Guzik, N. S. Sariciftci, Org. Electron. 2014, 15, 3521-3528.
E. D. Głowacki, M. Irimia-Vladu, M. Kaltenbrunner, J. Gsiorowski, M. S. White, U. Monkowius, G. Romanazzi, G. P. Suranna, P. Mastrorilli, T. Sekitani, S. Bauer, T. Someya, L. Torsi, N. S. Sariciftci, Adv. Mater. 2013, 25, 1563-1569.
E. Daniel Głowacki, L. Leonat, M. Irimia-Vladu, R. Schwödiauer, M. Ullah, H. Sitter, S. Bauer, N. Serdar Sariciftci, Appl. Phys. Lett. 2012, 101, 023305.
F. Bruni, M. Sassi, M. Campione, U. Giovanella, R. Ruffo, S. Luzzati, F. Meinardi, L. Beverina, S. Brovelli, Adv. Funct. Mater. 2014, 7410-7419.
C. Liu, S. Dong, P. Cai, P. Liu, S. Liu, J. Chen, F. Liu, L. Ying, T. P. Russell, F. Huang, Y. Cao, ACS Appl. Mater. Interfaces 2015, 7, 9038-9051.
S. Mattiello, A. Sanzone, P. Brazzo, M. Sassi, L. Beverina, Eur. J. Org. Chem. 2015, 5723-5729.
Z.-H. Guo, N. Ai, C. R. McBroom, T. Yuan, Y.-H. Lin, M. Roders, C. Zhu, A. L. Ayzner, J. Pei, L. Fang, Polym. Chem. 2016, 7, 648-655.
I. Maqueira-Albo, G. E. Bonacchini, G. Dell′Erba, G. Pace, M. Sassi, M. Rooney, R. Resel, L. Beverina, M. Caironi, J. Mater. Chem. C 2017, 5, 11522-11531.
L. Beverina, M. Rooney, R. Ruffo, M. Sassi, F. Carulli, S. Luzzati, R. Resel, B. Schrode, Org. Photonics Photovolt. 2018, 6, 8-16.
H. Yan, Z. Chen, Y. Zheng, C. Newman, J. R. Quinn, F. Dötz, M. Kastler, A. Facchetti, Nature 2008, 457, 679-686.
M. Sommer, J. Mater. Chem. C 2014, 2, 3088-3098.
S. Hillebrandt, T. Adermann, M. Alt, J. Schinke, T. Glaser, E. Mankel, G. Hernandez-Sosa, W. Jaegermann, U. Lemmer, A. Pucci, W. Kowalsky, K. Müllen, R. Lovrincic, M. Hamburger, ACS Appl. Mater. Interfaces 2016, 8, 4940-4945.
F. Nübling, H. Komber, M. Sommer, Macromolecules 2017, 50, 1909-1918.
R. Matsidik, H. Komber, M. Sommer, ACS Macro Lett. 2015, 1346-1350.
R. Matsidik, H. Komber, A. Luzio, M. Caironi, M. Sommer, J. Am. Chem. Soc. 2015, 137, 6705-6711.
J. Xie, W. Chen, Z. Wang, K. C. W. Jie, M. Liu, Q. Zhang, Chem. Asian J. 2017, 12, 868-876.
R. J. Kline, M. D. McGehee, E. N. Kadnikova, J. Liu, J. M. J. Frechet, M. F. Toney Macromolecules 2005, 38, 3312-3319.
A. C. Arias, J. D. MacKenzie, I. McCulloch, J. Rivnay, A. Salleo Chem. Rev. 2010, 110, 3-24.