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Highly Planarized Naphthalene Diimide–Bifuran Copolymers with Unexpected Charge Transport Performance

[Image: see text] The synthesis, characterization, and charge transport performance of novel copolymers PNDIFu2 made from alternating naphthalene diimide (NDI) and bifuran (Fu2) units are reported. Usage of potentially biomass-derived Fu2 as alternating repeat unit enables flattened polymer backbone...

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Autores principales: Matsidik, Rukiya, Luzio, Alessandro, Askin, Özge, Fazzi, Daniele, Sepe, Alessandro, Steiner, Ullrich, Komber, Hartmut, Caironi, Mario, Sommer, Michael
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5584907/
https://www.ncbi.nlm.nih.gov/pubmed/28890605
http://dx.doi.org/10.1021/acs.chemmater.6b05313
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author Matsidik, Rukiya
Luzio, Alessandro
Askin, Özge
Fazzi, Daniele
Sepe, Alessandro
Steiner, Ullrich
Komber, Hartmut
Caironi, Mario
Sommer, Michael
author_facet Matsidik, Rukiya
Luzio, Alessandro
Askin, Özge
Fazzi, Daniele
Sepe, Alessandro
Steiner, Ullrich
Komber, Hartmut
Caironi, Mario
Sommer, Michael
author_sort Matsidik, Rukiya
collection PubMed
description [Image: see text] The synthesis, characterization, and charge transport performance of novel copolymers PNDIFu2 made from alternating naphthalene diimide (NDI) and bifuran (Fu2) units are reported. Usage of potentially biomass-derived Fu2 as alternating repeat unit enables flattened polymer backbones due to reduced steric interactions between the imide oxygens and Fu2 units, as seen by density functional theory (DFT) calculations and UV–vis spectroscopy. Aggregation of PNDIFu2 in solution is enhanced if compared to the analogous NDI–bithiophene (T2) copolymers PNDIT2, occurring in all solvents and temperatures probed. PNDIFu2 features a smaller π–π stacking distance of 0.35 nm compared to 0.39 nm seen for PNDIT2. Alignment of aggregates in films is achieved by using off-center spin coating, whereby PNDIFu2 exhibits a stronger dichroic ratio and transport anisotropy in field-effect transistors (FET) compared to PNDIT2, with an overall good electron mobility of 0.21 cm(2)/(V s). Despite an enhanced backbone planarity, the smaller π–π stacking and the enhanced charge transport anisotropy, the electron mobility of PNDIFu2 is about three times lower compared to PNDIT2. Density functional theory calculations suggest that charge transport in PNDIFu2 is limited by enhanced polaron localization compared to PNDIT2.
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spelling pubmed-55849072017-09-06 Highly Planarized Naphthalene Diimide–Bifuran Copolymers with Unexpected Charge Transport Performance Matsidik, Rukiya Luzio, Alessandro Askin, Özge Fazzi, Daniele Sepe, Alessandro Steiner, Ullrich Komber, Hartmut Caironi, Mario Sommer, Michael Chem Mater [Image: see text] The synthesis, characterization, and charge transport performance of novel copolymers PNDIFu2 made from alternating naphthalene diimide (NDI) and bifuran (Fu2) units are reported. Usage of potentially biomass-derived Fu2 as alternating repeat unit enables flattened polymer backbones due to reduced steric interactions between the imide oxygens and Fu2 units, as seen by density functional theory (DFT) calculations and UV–vis spectroscopy. Aggregation of PNDIFu2 in solution is enhanced if compared to the analogous NDI–bithiophene (T2) copolymers PNDIT2, occurring in all solvents and temperatures probed. PNDIFu2 features a smaller π–π stacking distance of 0.35 nm compared to 0.39 nm seen for PNDIT2. Alignment of aggregates in films is achieved by using off-center spin coating, whereby PNDIFu2 exhibits a stronger dichroic ratio and transport anisotropy in field-effect transistors (FET) compared to PNDIT2, with an overall good electron mobility of 0.21 cm(2)/(V s). Despite an enhanced backbone planarity, the smaller π–π stacking and the enhanced charge transport anisotropy, the electron mobility of PNDIFu2 is about three times lower compared to PNDIT2. Density functional theory calculations suggest that charge transport in PNDIFu2 is limited by enhanced polaron localization compared to PNDIT2. American Chemical Society 2017-06-13 2017-07-11 /pmc/articles/PMC5584907/ /pubmed/28890605 http://dx.doi.org/10.1021/acs.chemmater.6b05313 Text en Copyright © 2017 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Matsidik, Rukiya
Luzio, Alessandro
Askin, Özge
Fazzi, Daniele
Sepe, Alessandro
Steiner, Ullrich
Komber, Hartmut
Caironi, Mario
Sommer, Michael
Highly Planarized Naphthalene Diimide–Bifuran Copolymers with Unexpected Charge Transport Performance
title Highly Planarized Naphthalene Diimide–Bifuran Copolymers with Unexpected Charge Transport Performance
title_full Highly Planarized Naphthalene Diimide–Bifuran Copolymers with Unexpected Charge Transport Performance
title_fullStr Highly Planarized Naphthalene Diimide–Bifuran Copolymers with Unexpected Charge Transport Performance
title_full_unstemmed Highly Planarized Naphthalene Diimide–Bifuran Copolymers with Unexpected Charge Transport Performance
title_short Highly Planarized Naphthalene Diimide–Bifuran Copolymers with Unexpected Charge Transport Performance
title_sort highly planarized naphthalene diimide–bifuran copolymers with unexpected charge transport performance
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5584907/
https://www.ncbi.nlm.nih.gov/pubmed/28890605
http://dx.doi.org/10.1021/acs.chemmater.6b05313
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