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Synthesis and Characterization of Polymers Containing Ethynylene and Ethynylene-Thiophene Based Alternating Polymers Containing 2,1,3-Linked Naphthothiadiazole Units as Acceptor Linked with Fluorine as Donor: Electrochemical and Spectroscopic Studies
The effect of ethynylene or ethynylene–thiophene spacers on the band gap of alternating polymers, containing 4,9-naphthothiadiazole units as an acceptor and 2,7-linked fluorene repeat units as a donor, were investigated. The Sonogashira coupling reaction was employed to prepare the two novel copolym...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9571599/ https://www.ncbi.nlm.nih.gov/pubmed/36236087 http://dx.doi.org/10.3390/polym14194139 |
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author | Al-Azzawi, Ahmed G. S. Dannoun, Elham M. A. Aziz, Shujahadeen B. Iraqi, Ahmed Al-Saeedi, Sameerah I. Nofal, Muaffaq M. Murad, Ary R. |
author_facet | Al-Azzawi, Ahmed G. S. Dannoun, Elham M. A. Aziz, Shujahadeen B. Iraqi, Ahmed Al-Saeedi, Sameerah I. Nofal, Muaffaq M. Murad, Ary R. |
author_sort | Al-Azzawi, Ahmed G. S. |
collection | PubMed |
description | The effect of ethynylene or ethynylene–thiophene spacers on the band gap of alternating polymers, containing 4,9-naphthothiadiazole units as an acceptor and 2,7-linked fluorene repeat units as a donor, were investigated. The Sonogashira coupling reaction was employed to prepare the two novel copolymers, namely ((9,9-dioctyl-fluorene)-2,7-diethynylene-alt-4,9-2,1,3-naphthothiadiazole (PFDENT) and poly(5,5’-(9,9-dioctyl-fluorene-2,7-diyl)bis(ethynyl-2-thienyl)-alt-4,9-(2,1,3-naphthothiadiazole) (PFDTENT). The optical, electrochemical and thermal properties of the two obtained polymers were widely investigated and compared. Both resulting polymers showed low solubility in common organic solvents and moderate molecular weights. It is believed that the introduction of acetylene linkers rather than acetylene–thiophene spacers on the polymer chains reduces the steric hindrance between the donor and acceptor units which leads to the adoption of more planar structures of polymeric chains, resulting in decreased molecular weights of the resulting conjugated polymers. Thus, both ethynylene-based polymers and ethynylene–thiophene-based polymers showed red-shifted absorption maxima compared to their counterpart (thiophene-based polymer), owing to the adoption of more planar structures. Optical studies revealed that the new ethynylene and ethynylene–thiophene-based polymers displayed low band gaps compared to their thiophene analogue polymer PFDTNT. Both resulting polymers showed good thermal stability. X-ray diffraction (XRD) patterns of both polymers revealed that PFDENT and PFDTENT possessed an amorphous nature in solid state. |
format | Online Article Text |
id | pubmed-9571599 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-95715992022-10-17 Synthesis and Characterization of Polymers Containing Ethynylene and Ethynylene-Thiophene Based Alternating Polymers Containing 2,1,3-Linked Naphthothiadiazole Units as Acceptor Linked with Fluorine as Donor: Electrochemical and Spectroscopic Studies Al-Azzawi, Ahmed G. S. Dannoun, Elham M. A. Aziz, Shujahadeen B. Iraqi, Ahmed Al-Saeedi, Sameerah I. Nofal, Muaffaq M. Murad, Ary R. Polymers (Basel) Article The effect of ethynylene or ethynylene–thiophene spacers on the band gap of alternating polymers, containing 4,9-naphthothiadiazole units as an acceptor and 2,7-linked fluorene repeat units as a donor, were investigated. The Sonogashira coupling reaction was employed to prepare the two novel copolymers, namely ((9,9-dioctyl-fluorene)-2,7-diethynylene-alt-4,9-2,1,3-naphthothiadiazole (PFDENT) and poly(5,5’-(9,9-dioctyl-fluorene-2,7-diyl)bis(ethynyl-2-thienyl)-alt-4,9-(2,1,3-naphthothiadiazole) (PFDTENT). The optical, electrochemical and thermal properties of the two obtained polymers were widely investigated and compared. Both resulting polymers showed low solubility in common organic solvents and moderate molecular weights. It is believed that the introduction of acetylene linkers rather than acetylene–thiophene spacers on the polymer chains reduces the steric hindrance between the donor and acceptor units which leads to the adoption of more planar structures of polymeric chains, resulting in decreased molecular weights of the resulting conjugated polymers. Thus, both ethynylene-based polymers and ethynylene–thiophene-based polymers showed red-shifted absorption maxima compared to their counterpart (thiophene-based polymer), owing to the adoption of more planar structures. Optical studies revealed that the new ethynylene and ethynylene–thiophene-based polymers displayed low band gaps compared to their thiophene analogue polymer PFDTNT. Both resulting polymers showed good thermal stability. X-ray diffraction (XRD) patterns of both polymers revealed that PFDENT and PFDTENT possessed an amorphous nature in solid state. MDPI 2022-10-03 /pmc/articles/PMC9571599/ /pubmed/36236087 http://dx.doi.org/10.3390/polym14194139 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Al-Azzawi, Ahmed G. S. Dannoun, Elham M. A. Aziz, Shujahadeen B. Iraqi, Ahmed Al-Saeedi, Sameerah I. Nofal, Muaffaq M. Murad, Ary R. Synthesis and Characterization of Polymers Containing Ethynylene and Ethynylene-Thiophene Based Alternating Polymers Containing 2,1,3-Linked Naphthothiadiazole Units as Acceptor Linked with Fluorine as Donor: Electrochemical and Spectroscopic Studies |
title | Synthesis and Characterization of Polymers Containing Ethynylene and Ethynylene-Thiophene Based Alternating Polymers Containing 2,1,3-Linked Naphthothiadiazole Units as Acceptor Linked with Fluorine as Donor: Electrochemical and Spectroscopic Studies |
title_full | Synthesis and Characterization of Polymers Containing Ethynylene and Ethynylene-Thiophene Based Alternating Polymers Containing 2,1,3-Linked Naphthothiadiazole Units as Acceptor Linked with Fluorine as Donor: Electrochemical and Spectroscopic Studies |
title_fullStr | Synthesis and Characterization of Polymers Containing Ethynylene and Ethynylene-Thiophene Based Alternating Polymers Containing 2,1,3-Linked Naphthothiadiazole Units as Acceptor Linked with Fluorine as Donor: Electrochemical and Spectroscopic Studies |
title_full_unstemmed | Synthesis and Characterization of Polymers Containing Ethynylene and Ethynylene-Thiophene Based Alternating Polymers Containing 2,1,3-Linked Naphthothiadiazole Units as Acceptor Linked with Fluorine as Donor: Electrochemical and Spectroscopic Studies |
title_short | Synthesis and Characterization of Polymers Containing Ethynylene and Ethynylene-Thiophene Based Alternating Polymers Containing 2,1,3-Linked Naphthothiadiazole Units as Acceptor Linked with Fluorine as Donor: Electrochemical and Spectroscopic Studies |
title_sort | synthesis and characterization of polymers containing ethynylene and ethynylene-thiophene based alternating polymers containing 2,1,3-linked naphthothiadiazole units as acceptor linked with fluorine as donor: electrochemical and spectroscopic studies |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9571599/ https://www.ncbi.nlm.nih.gov/pubmed/36236087 http://dx.doi.org/10.3390/polym14194139 |
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