Structural‐Functional Properties of Asymmetric Fluoro‐Alkoxy Substituted Benzothiadiazole Homopolymers with Flanked Chalcogen‐Based Heterocycles
<p dir="ltr">The synthesis and characterization of asymmetric alkoxy‐ are reported, fluoro‐benzothiadiazole (BT) acceptor core derivatized with a series of six different heterocycles (selenophene, thiophene, furan, 5‐thiazole, 2‐thiazole and 2‐oxazole). The effect of the flanked‐hete...
Saved in:
| Main Author: | |
|---|---|
| Other Authors: | , , , , , |
| Published: |
2022
|
| Subjects: | |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1864513547376001024 |
|---|---|
| author | Marc Comí (21406910) |
| author2 | Salvador Moncho (407916) Salahuddin Attar (2734063) Maciej Barłóg (21406913) Edward Brothers (21406916) Hassan S. Bazzi (1364424) Mohammed Al‐Hashimi (21406919) |
| author2_role | author author author author author author |
| author_facet | Marc Comí (21406910) Salvador Moncho (407916) Salahuddin Attar (2734063) Maciej Barłóg (21406913) Edward Brothers (21406916) Hassan S. Bazzi (1364424) Mohammed Al‐Hashimi (21406919) |
| author_role | author |
| dc.creator.none.fl_str_mv | Marc Comí (21406910) Salvador Moncho (407916) Salahuddin Attar (2734063) Maciej Barłóg (21406913) Edward Brothers (21406916) Hassan S. Bazzi (1364424) Mohammed Al‐Hashimi (21406919) |
| dc.date.none.fl_str_mv | 2022-10-26T15:00:00Z |
| dc.identifier.none.fl_str_mv | 10.1002/marc.202200731 |
| dc.relation.none.fl_str_mv | https://figshare.com/articles/journal_contribution/Structural_Functional_Properties_of_Asymmetric_Fluoro_Alkoxy_Substituted_Benzothiadiazole_Homopolymers_with_Flanked_Chalcogen_Based_Heterocycles/29126708 |
| dc.rights.none.fl_str_mv | CC BY 4.0 info:eu-repo/semantics/openAccess |
| dc.subject.none.fl_str_mv | Chemical sciences Physical chemistry Engineering Materials engineering Chalcogen atoms Homopolymers Optical properties Thermal properties Electrochemical properties Computational analysis |
| dc.title.none.fl_str_mv | Structural‐Functional Properties of Asymmetric Fluoro‐Alkoxy Substituted Benzothiadiazole Homopolymers with Flanked Chalcogen‐Based Heterocycles |
| dc.type.none.fl_str_mv | Text Journal contribution info:eu-repo/semantics/publishedVersion text contribution to journal |
| description | <p dir="ltr">The synthesis and characterization of asymmetric alkoxy‐ are reported, fluoro‐benzothiadiazole (BT) acceptor core derivatized with a series of six different heterocycles (selenophene, thiophene, furan, 5‐thiazole, 2‐thiazole and 2‐oxazole). The effect of the flanked‐heterocycles containing different chalcogen atoms of the six homopolymers (<b>HPX</b>) is studied using optical, thermal, electrochemical, and computational analysis. Computational calculations indicate a strong relationship between the most stable conformation for each homopolymer and their bearing heterocycle, thus homopolymers <b>HPSe’</b>, <b>HPTp’,</b> <b>HPFu</b>’, and <b>HPTzC5</b>, adopted the syn‐syn and syn‐anti conformations due to their noncovalent interactions with shorter distances, while <b>HPTzC2’ </b>and <b>HPOx’ </b>demonstrate preference for the anti‐anti conformation. Optical property studies of the homopolymers reveal a strong red‐shift in solution and film upon exchanging the chalcogen atom from Oxygen < Sulfur < Selenium in <b>HPFu, HPTp, </b>and<b> HPSe</b>, respectively. In addition, deeper highest occupied molecular orbital (HOMO) energy levels are observed when the donor‐acceptor moieties (<b>HPSe, HPTp, </b>and<b> HPFu</b>) are substituted for the acceptor‐acceptor systems such as <b>HPTzC5, HPTzC2</b>, and <b>HPOx</b>. Improved packing and morphology are exhibited for the donor‐acceptor homopolymers. Thus, having a flanked heterocycle containing different chalcogen‐atoms in polymeric systems is one way of tuning the physicochemical properties of conjugated materials for optoelectronic applications.</p><h2>Other Information</h2><p dir="ltr">Published in: Macromolecular Rapid Communications<br>License: <a href="http://creativecommons.org/licenses/by/4.0/" target="_blank">http://creativecommons.org/licenses/by/4.0/</a><br>See article on publisher's website: <a href="https://dx.doi.org/10.1002/marc.202200731" target="_blank">https://dx.doi.org/10.1002/marc.202200731</a></p> |
| eu_rights_str_mv | openAccess |
| id | Manara2_8f3729d4fce3efd51ef924fd32e6fe0b |
| identifier_str_mv | 10.1002/marc.202200731 |
| network_acronym_str | Manara2 |
| network_name_str | Manara2 |
| oai_identifier_str | oai:figshare.com:article/29126708 |
| publishDate | 2022 |
| repository.mail.fl_str_mv | |
| repository.name.fl_str_mv | |
| repository_id_str | |
| rights_invalid_str_mv | CC BY 4.0 |
| spelling | Structural‐Functional Properties of Asymmetric Fluoro‐Alkoxy Substituted Benzothiadiazole Homopolymers with Flanked Chalcogen‐Based HeterocyclesMarc Comí (21406910)Salvador Moncho (407916)Salahuddin Attar (2734063)Maciej Barłóg (21406913)Edward Brothers (21406916)Hassan S. Bazzi (1364424)Mohammed Al‐Hashimi (21406919)Chemical sciencesPhysical chemistryEngineeringMaterials engineeringChalcogen atomsHomopolymersOptical propertiesThermal propertiesElectrochemical propertiesComputational analysis<p dir="ltr">The synthesis and characterization of asymmetric alkoxy‐ are reported, fluoro‐benzothiadiazole (BT) acceptor core derivatized with a series of six different heterocycles (selenophene, thiophene, furan, 5‐thiazole, 2‐thiazole and 2‐oxazole). The effect of the flanked‐heterocycles containing different chalcogen atoms of the six homopolymers (<b>HPX</b>) is studied using optical, thermal, electrochemical, and computational analysis. Computational calculations indicate a strong relationship between the most stable conformation for each homopolymer and their bearing heterocycle, thus homopolymers <b>HPSe’</b>, <b>HPTp’,</b> <b>HPFu</b>’, and <b>HPTzC5</b>, adopted the syn‐syn and syn‐anti conformations due to their noncovalent interactions with shorter distances, while <b>HPTzC2’ </b>and <b>HPOx’ </b>demonstrate preference for the anti‐anti conformation. Optical property studies of the homopolymers reveal a strong red‐shift in solution and film upon exchanging the chalcogen atom from Oxygen < Sulfur < Selenium in <b>HPFu, HPTp, </b>and<b> HPSe</b>, respectively. In addition, deeper highest occupied molecular orbital (HOMO) energy levels are observed when the donor‐acceptor moieties (<b>HPSe, HPTp, </b>and<b> HPFu</b>) are substituted for the acceptor‐acceptor systems such as <b>HPTzC5, HPTzC2</b>, and <b>HPOx</b>. Improved packing and morphology are exhibited for the donor‐acceptor homopolymers. Thus, having a flanked heterocycle containing different chalcogen‐atoms in polymeric systems is one way of tuning the physicochemical properties of conjugated materials for optoelectronic applications.</p><h2>Other Information</h2><p dir="ltr">Published in: Macromolecular Rapid Communications<br>License: <a href="http://creativecommons.org/licenses/by/4.0/" target="_blank">http://creativecommons.org/licenses/by/4.0/</a><br>See article on publisher's website: <a href="https://dx.doi.org/10.1002/marc.202200731" target="_blank">https://dx.doi.org/10.1002/marc.202200731</a></p>2022-10-26T15:00:00ZTextJournal contributioninfo:eu-repo/semantics/publishedVersiontextcontribution to journal10.1002/marc.202200731https://figshare.com/articles/journal_contribution/Structural_Functional_Properties_of_Asymmetric_Fluoro_Alkoxy_Substituted_Benzothiadiazole_Homopolymers_with_Flanked_Chalcogen_Based_Heterocycles/29126708CC BY 4.0info:eu-repo/semantics/openAccessoai:figshare.com:article/291267082022-10-26T15:00:00Z |
| spellingShingle | Structural‐Functional Properties of Asymmetric Fluoro‐Alkoxy Substituted Benzothiadiazole Homopolymers with Flanked Chalcogen‐Based Heterocycles Marc Comí (21406910) Chemical sciences Physical chemistry Engineering Materials engineering Chalcogen atoms Homopolymers Optical properties Thermal properties Electrochemical properties Computational analysis |
| status_str | publishedVersion |
| title | Structural‐Functional Properties of Asymmetric Fluoro‐Alkoxy Substituted Benzothiadiazole Homopolymers with Flanked Chalcogen‐Based Heterocycles |
| title_full | Structural‐Functional Properties of Asymmetric Fluoro‐Alkoxy Substituted Benzothiadiazole Homopolymers with Flanked Chalcogen‐Based Heterocycles |
| title_fullStr | Structural‐Functional Properties of Asymmetric Fluoro‐Alkoxy Substituted Benzothiadiazole Homopolymers with Flanked Chalcogen‐Based Heterocycles |
| title_full_unstemmed | Structural‐Functional Properties of Asymmetric Fluoro‐Alkoxy Substituted Benzothiadiazole Homopolymers with Flanked Chalcogen‐Based Heterocycles |
| title_short | Structural‐Functional Properties of Asymmetric Fluoro‐Alkoxy Substituted Benzothiadiazole Homopolymers with Flanked Chalcogen‐Based Heterocycles |
| title_sort | Structural‐Functional Properties of Asymmetric Fluoro‐Alkoxy Substituted Benzothiadiazole Homopolymers with Flanked Chalcogen‐Based Heterocycles |
| topic | Chemical sciences Physical chemistry Engineering Materials engineering Chalcogen atoms Homopolymers Optical properties Thermal properties Electrochemical properties Computational analysis |