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Journal of Materials Chemistry
Poverenov, E., Department of Organic Chemistry, Weizmann Institute of Science, Rehovot 76100, Israel, Department of Food Science, Volcani Center, ARO, Bet Dagan, Israel
Sheynin, Y., 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
Leitus, G., Department of Chemical Research Support, Weizmann Institute of Science, Rehovot 76100, Israel
Perepichka, I.F., School of Chemistry, Bangor University, Bangor, Gwynedd LL57 2UW, United Kingdom
Bendikov, M., Department of Organic Chemistry, Weizmann Institute of Science, Rehovot 76100, Israel
In this work, we prepared a series of new conjugated polyselenophenes that, in the 3,4-positions of the selenophene ring, have oxygen or sulfur substituents bridged by a phenylene moiety. Such substitution of a conjugated backbone produces a skeleton that has only planar units, does not have stereo centers, and offers the potential to structurally modify the polymer without impairing its conjugation. The reported polyselenophenes exhibit significantly different properties as a function of the heteroatom. The selenophene backbone combined with a phenylene periphery creates the rare combination of a low-band gap, low HOMO energy level, and a flat skeleton, which is desired for many optoelectronic applications. The properties of the phenylene-bridged polyselenophenes were compared with those of their polythiophene analogs. The polyselenophenes obtained in this work have a lower band gap and higher planarity than polythiophenes and their monomers electropolymerize more easily. Theoretical studies support the experimental findings about rigidity and band gap changes. © 2012 The Royal Society of Chemistry.
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Flat conjugated polymers combining a relatively low HOMO energy level and band gap: Polyselenophenes versus polythiophenes
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Poverenov, E., Department of Organic Chemistry, Weizmann Institute of Science, Rehovot 76100, Israel, Department of Food Science, Volcani Center, ARO, Bet Dagan, Israel
Sheynin, Y., 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
Leitus, G., Department of Chemical Research Support, Weizmann Institute of Science, Rehovot 76100, Israel
Perepichka, I.F., School of Chemistry, Bangor University, Bangor, Gwynedd LL57 2UW, United Kingdom
Bendikov, M., Department of Organic Chemistry, Weizmann Institute of Science, Rehovot 76100, Israel
Flat conjugated polymers combining a relatively low HOMO energy level and band gap: Polyselenophenes versus polythiophenes
In this work, we prepared a series of new conjugated polyselenophenes that, in the 3,4-positions of the selenophene ring, have oxygen or sulfur substituents bridged by a phenylene moiety. Such substitution of a conjugated backbone produces a skeleton that has only planar units, does not have stereo centers, and offers the potential to structurally modify the polymer without impairing its conjugation. The reported polyselenophenes exhibit significantly different properties as a function of the heteroatom. The selenophene backbone combined with a phenylene periphery creates the rare combination of a low-band gap, low HOMO energy level, and a flat skeleton, which is desired for many optoelectronic applications. The properties of the phenylene-bridged polyselenophenes were compared with those of their polythiophene analogs. The polyselenophenes obtained in this work have a lower band gap and higher planarity than polythiophenes and their monomers electropolymerize more easily. Theoretical studies support the experimental findings about rigidity and band gap changes. © 2012 The Royal Society of Chemistry.
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