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Unusual doping of donor-acceptor-type conjugated polymers using lewis acids
Year:
2014
Authors :
Poverenov, Elena
;
.
Volume :
136
Co-Authors:
Poverenov, E., Department of Organic Chemistry, Weizmann Institute of Science, Rehovot, 76100, Israel
Zamoshchik, N., Department of Organic Chemistry, Weizmann Institute of Science, Rehovot, 76100, Israel
Patra, A., Department of Organic Chemistry, Weizmann Institute of Science, Rehovot, 76100, Israel
Ridelman, Y., Department of Organic Chemistry, Weizmann Institute of Science, Rehovot, 76100, Israel
Bendikov, M., Department of Organic Chemistry, Weizmann Institute of Science, Rehovot, 76100, Israel
Facilitators :
From page:
5138
To page:
5149
(
Total pages:
12
)
Abstract:
Conjugated polymers that can undergo unusual nonoxidative doping were designed. A series of polymers based on donor-acceptor-donor (DAD) moieties 2,1,3-benzoselenadiazole, 2,1,3-benzothiadiazole, 2,1,3-benzoxadiazolebenzo[2,1, 5]oxodiazole, and 2-hexylbenzotriazole as acceptor fragments and 3,4-ethylenedioxyselenophene (EDOS) and 3,4-ethylenedioxythiophene (EDOT) as donor fragments was prepared. When the studied polymers were reacted with Lewis acids and bases, notable optical switching and conductivity changes were observed, evidencing the exceptional case of efficient nonoxidative doping/dedoping. Remarkably, in previously reported works, coordination of Lewis acids causes band gap shift but not doping of the conductive polymer, while in the present study, coordination of Lewis acid to highly donating EDOT and EDOS moieties led to polymer doping. The polymers show remarkable stability after numerous switching cycles from neutral to doped states and vice versa and can be switched both electrochemically and chemically. The reactivity of the prepared polymers with Lewis acids and bases of different strengths was studied. Calculation studies of the Lewis acid coordination mode, its effect on polymer energies and band gap, support the unusual doping. The reported doping approach opens up the possibility to control the conjugation, color change, and switching of states of conjugated polymers without oxidation. © 2014 American Chemical Society.
Note:
Related Files :
2,1,3 benzoxadiazolebenzo[2,1,5]oxodiazole
Lewis acids and basis
Synthesis
unclassified drug
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More details
DOI :
10.1021/ja501024n
Article number:
Affiliations:
Database:
Scopus
Publication Type:
article
;
.
Language:
English
Editors' remarks:
ID:
31240
Last updated date:
02/03/2022 17:27
Creation date:
17/04/2018 01:00
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Scientific Publication
Unusual doping of donor-acceptor-type conjugated polymers using lewis acids
136
Poverenov, E., Department of Organic Chemistry, Weizmann Institute of Science, Rehovot, 76100, Israel
Zamoshchik, N., Department of Organic Chemistry, Weizmann Institute of Science, Rehovot, 76100, Israel
Patra, A., Department of Organic Chemistry, Weizmann Institute of Science, Rehovot, 76100, Israel
Ridelman, Y., Department of Organic Chemistry, Weizmann Institute of Science, Rehovot, 76100, Israel
Bendikov, M., Department of Organic Chemistry, Weizmann Institute of Science, Rehovot, 76100, Israel
Unusual doping of donor-acceptor-type conjugated polymers using lewis acids
Conjugated polymers that can undergo unusual nonoxidative doping were designed. A series of polymers based on donor-acceptor-donor (DAD) moieties 2,1,3-benzoselenadiazole, 2,1,3-benzothiadiazole, 2,1,3-benzoxadiazolebenzo[2,1, 5]oxodiazole, and 2-hexylbenzotriazole as acceptor fragments and 3,4-ethylenedioxyselenophene (EDOS) and 3,4-ethylenedioxythiophene (EDOT) as donor fragments was prepared. When the studied polymers were reacted with Lewis acids and bases, notable optical switching and conductivity changes were observed, evidencing the exceptional case of efficient nonoxidative doping/dedoping. Remarkably, in previously reported works, coordination of Lewis acids causes band gap shift but not doping of the conductive polymer, while in the present study, coordination of Lewis acid to highly donating EDOT and EDOS moieties led to polymer doping. The polymers show remarkable stability after numerous switching cycles from neutral to doped states and vice versa and can be switched both electrochemically and chemically. The reactivity of the prepared polymers with Lewis acids and bases of different strengths was studied. Calculation studies of the Lewis acid coordination mode, its effect on polymer energies and band gap, support the unusual doping. The reported doping approach opens up the possibility to control the conjugation, color change, and switching of states of conjugated polymers without oxidation. © 2014 American Chemical Society.
Scientific Publication
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