Publicação
Push-pull heterocyclic dyes based on pyrrole and thiophene: synthesis and evaluation of their optical, redox and photovoltaic properties
| Resumo: | Three heterocyclic dyes were synthesized having in mind the changes in the photovoltaic, optical and redox properties by functionalization of 5-aryl-thieno[3,2-<i>b</i>]thiophene, 5-arylthiophene and <i>bis</i>-methylpyrrolylthiophene π-bridges with different donor, acceptor/anchoring groups. Knoevenagel condensation of the aldehyde precursors with 2-cyanoacetic acid was used to prepare the donor-acceptor functionalized heterocyclic molecules. These organic metal-free dyes are constituted by thieno[3,2-<i>b</i>]thiophene, arylthiophene, <i>bis</i>-methylpyrrolylthiophene, spacers and one or two cyanoacetic acid acceptor groups and different electron donor groups (alkoxyl, and pyrrole electron-rich heterocycle). The evaluation of the redox, optical and photovoltaic properties of these compounds indicate that 5-aryl-thieno[3,2-<i>b</i>]thiophene-based dye functionalized with an ethoxyl electron donor and a cyanoacetic acid electron acceptor group/anchoring moiety displays as sensitizer for DSSCs the best conversion efficiency (2.21%). It is mainly assigned to the higher molar extinction coefficient, long π-conjugation of the heterocyclic system, higher oxidation potential and strong electron donating capacity of the ethoxyl group compared to the pirrolyl moiety. |
|---|---|
| Autores principais: | Fernandes, Sara Sofia Marques |
| Outros Autores: | Castro, Maria Cidália Rodrigues; Ivanou, Dzmitry; Mendes, Adélio; Raposo, M. Manuela M. |
| Assunto: | Heterocyclic push-pull dyes Thiophene Pyrrole Dye-sensitized solar cells Auxiliary donor/acceptor heterocycles Synthesis auxiliary donor acceptor heterocycles |
| Ano: | 2022 |
| País: | Portugal |
| Tipo de documento: | artigo |
| Tipo de acesso: | acesso aberto |
| Instituição associada: | Universidade do Minho |
| Idioma: | inglês |
| Origem: | RepositóriUM - Universidade do Minho |
| _version_ | 1866875868917268480 |
|---|---|
| author | Fernandes, Sara Sofia Marques |
| author2 | Castro, Maria Cidália Rodrigues Ivanou, Dzmitry Mendes, Adélio Raposo, M. Manuela M. |
| author2_role | author author author author |
| author_facet | Fernandes, Sara Sofia Marques Castro, Maria Cidália Rodrigues Ivanou, Dzmitry Mendes, Adélio Raposo, M. Manuela M. |
| author_role | author |
| contributor_name_str_mv | Universidade do Minho |
| country_str | PT |
| creators_json_txt | [{\"Person.name\":\"Fernandes, Sara Sofia Marques\"},{\"Person.name\":\"Castro, Maria Cidália Rodrigues\"},{\"Person.name\":\"Ivanou, Dzmitry\"},{\"Person.name\":\"Mendes, Adélio\"},{\"Person.name\":\"Raposo, M. Manuela M.\"}] |
| datacite.contributors.contributor.contributorName.fl_str_mv | Universidade do Minho |
| datacite.creators.creator.creatorName.fl_str_mv | Fernandes, Sara Sofia Marques Castro, Maria Cidália Rodrigues Ivanou, Dzmitry Mendes, Adélio Raposo, M. Manuela M. |
| datacite.date.Accepted.fl_str_mv | 2022-01-01T00:00:00Z |
| datacite.date.available.fl_str_mv | 2022-06-08T09:17:12Z |
| datacite.date.embargoed.fl_str_mv | 2022-06-08T09:17:12Z |
| datacite.rights.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| datacite.subjects.subject.fl_str_mv | Heterocyclic push-pull dyes Thiophene Pyrrole Dye-sensitized solar cells Auxiliary donor/acceptor heterocycles Synthesis auxiliary donor acceptor heterocycles |
| datacite.titles.title.fl_str_mv | Push-pull heterocyclic dyes based on pyrrole and thiophene: synthesis and evaluation of their optical, redox and photovoltaic properties |
| dc.contributor.none.fl_str_mv | Universidade do Minho |
| dc.creator.none.fl_str_mv | Fernandes, Sara Sofia Marques Castro, Maria Cidália Rodrigues Ivanou, Dzmitry Mendes, Adélio Raposo, M. Manuela M. |
| dc.date.Accepted.fl_str_mv | 2022-01-01T00:00:00Z |
| dc.date.available.fl_str_mv | 2022-06-08T09:17:12Z |
| dc.date.embargoed.fl_str_mv | 2022-06-08T09:17:12Z |
| dc.format.none.fl_str_mv | application/pdf |
| dc.identifier.none.fl_str_mv | https://hdl.handle.net/1822/78288 |
| dc.language.none.fl_str_mv | eng |
| dc.publisher.none.fl_str_mv | Multidisciplinary Digital Publishing Institute (MDPI) |
| dc.rights.cclincense.fl_str_mv | http://creativecommons.org/licenses/by/4.0/ |
| dc.rights.none.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| dc.rights.rights.copyright.fl_str_mv | openAccess |
| dc.subject.none.fl_str_mv | Heterocyclic push-pull dyes Thiophene Pyrrole Dye-sensitized solar cells Auxiliary donor/acceptor heterocycles Synthesis auxiliary donor acceptor heterocycles |
| dc.title.fl_str_mv | Push-pull heterocyclic dyes based on pyrrole and thiophene: synthesis and evaluation of their optical, redox and photovoltaic properties |
| dc.type.none.fl_str_mv | http://purl.org/coar/resource_type/c_6501 |
| description | Three heterocyclic dyes were synthesized having in mind the changes in the photovoltaic, optical and redox properties by functionalization of 5-aryl-thieno[3,2-<i>b</i>]thiophene, 5-arylthiophene and <i>bis</i>-methylpyrrolylthiophene π-bridges with different donor, acceptor/anchoring groups. Knoevenagel condensation of the aldehyde precursors with 2-cyanoacetic acid was used to prepare the donor-acceptor functionalized heterocyclic molecules. These organic metal-free dyes are constituted by thieno[3,2-<i>b</i>]thiophene, arylthiophene, <i>bis</i>-methylpyrrolylthiophene, spacers and one or two cyanoacetic acid acceptor groups and different electron donor groups (alkoxyl, and pyrrole electron-rich heterocycle). The evaluation of the redox, optical and photovoltaic properties of these compounds indicate that 5-aryl-thieno[3,2-<i>b</i>]thiophene-based dye functionalized with an ethoxyl electron donor and a cyanoacetic acid electron acceptor group/anchoring moiety displays as sensitizer for DSSCs the best conversion efficiency (2.21%). It is mainly assigned to the higher molar extinction coefficient, long π-conjugation of the heterocyclic system, higher oxidation potential and strong electron donating capacity of the ethoxyl group compared to the pirrolyl moiety. |
| dirty | 0 |
| eu_rights_str_mv | openAccess |
| format | article |
| fulltext.url.fl_str_mv | https://prod-dspace.uminho.pt/bitstreams/faeaf6af-a47a-4ab9-87e4-d195903f78f1/download |
| id | rum_aca84f931604e2b2e39a2d4ee8fb3db5 |
| identifier.url.fl_str_mv | https://hdl.handle.net/1822/78288 |
| instacron_str | repositorium |
| institution | Universidade do Minho |
| instname_str | Universidade do Minho |
| language | eng |
| network_acronym_str | rum |
| network_name_str | RepositóriUM - Universidade do Minho |
| oai_identifier_str | oai:repositorium.uminho.pt:1822/78288 |
| organization_str_mv | urn:organizationAcronym:repositorium |
| person_str_mv | Fernandes, Sara Sofia Marques Castro, Maria Cidália Rodrigues Ivanou, Dzmitry Mendes, Adélio Raposo, M. Manuela M. |
| publishDate | 2022 |
| publisher.none.fl_str_mv | Multidisciplinary Digital Publishing Institute (MDPI) |
| reponame_str | RepositóriUM - Universidade do Minho |
| repository_id_str | urn:repositoryAcronym:rum |
| service_str_mv | urn:repositoryAcronym:rum |
| spelling | engMultidisciplinary Digital Publishing Institute (MDPI)porThree heterocyclic dyes were synthesized having in mind the changes in the photovoltaic, optical and redox properties by functionalization of 5-aryl-thieno[3,2-<i>b</i>]thiophene, 5-arylthiophene and <i>bis</i>-methylpyrrolylthiophene π-bridges with different donor, acceptor/anchoring groups. Knoevenagel condensation of the aldehyde precursors with 2-cyanoacetic acid was used to prepare the donor-acceptor functionalized heterocyclic molecules. These organic metal-free dyes are constituted by thieno[3,2-<i>b</i>]thiophene, arylthiophene, <i>bis</i>-methylpyrrolylthiophene, spacers and one or two cyanoacetic acid acceptor groups and different electron donor groups (alkoxyl, and pyrrole electron-rich heterocycle). The evaluation of the redox, optical and photovoltaic properties of these compounds indicate that 5-aryl-thieno[3,2-<i>b</i>]thiophene-based dye functionalized with an ethoxyl electron donor and a cyanoacetic acid electron acceptor group/anchoring moiety displays as sensitizer for DSSCs the best conversion efficiency (2.21%). It is mainly assigned to the higher molar extinction coefficient, long π-conjugation of the heterocyclic system, higher oxidation potential and strong electron donating capacity of the ethoxyl group compared to the pirrolyl moiety.application/pdfporPush-pull heterocyclic dyes based on pyrrole and thiophene: synthesis and evaluation of their optical, redox and photovoltaic propertiesFernandes, Sara Sofia MarquesCastro, Maria Cidália RodriguesIvanou, DzmitryMendes, AdélioRaposo, M. Manuela M.HostingInstitutionOrganizationalUniversidade do Minhoe-mailmailto:repositorium@usdb.uminho.ptrepositorium@usdb.uminho.ptDOIIsPartOf10.3390/coatings120100342022-06-08T09:17:12Z20222022-01-20T15:24:23Z2022-01-01T00:00:00ZHandlehttps://hdl.handle.net/1822/78288http://purl.org/coar/access_right/c_abf2open accessHeterocyclic push-pull dyesThiophenePyrroleDye-sensitized solar cellsAuxiliary donor/acceptor heterocyclesSynthesisauxiliary donoracceptor heterocycles1413520 bytesliteraturehttp://purl.org/coar/resource_type/c_6501journal article2022http://creativecommons.org/licenses/by/4.0/openAccesshttp://purl.org/coar/access_right/c_abf2application/pdffulltexthttps://prod-dspace.uminho.pt/bitstreams/faeaf6af-a47a-4ab9-87e4-d195903f78f1/download |
| spellingShingle | Push-pull heterocyclic dyes based on pyrrole and thiophene: synthesis and evaluation of their optical, redox and photovoltaic properties Fernandes, Sara Sofia Marques Heterocyclic push-pull dyes Thiophene Pyrrole Dye-sensitized solar cells Auxiliary donor/acceptor heterocycles Synthesis auxiliary donor acceptor heterocycles |
| status | SINGLETON |
| subject.fl_str_mv | Heterocyclic push-pull dyes Thiophene Pyrrole Dye-sensitized solar cells Auxiliary donor/acceptor heterocycles Synthesis auxiliary donor acceptor heterocycles |
| title | Push-pull heterocyclic dyes based on pyrrole and thiophene: synthesis and evaluation of their optical, redox and photovoltaic properties |
| title_full | Push-pull heterocyclic dyes based on pyrrole and thiophene: synthesis and evaluation of their optical, redox and photovoltaic properties |
| title_fullStr | Push-pull heterocyclic dyes based on pyrrole and thiophene: synthesis and evaluation of their optical, redox and photovoltaic properties |
| title_full_unstemmed | Push-pull heterocyclic dyes based on pyrrole and thiophene: synthesis and evaluation of their optical, redox and photovoltaic properties |
| title_short | Push-pull heterocyclic dyes based on pyrrole and thiophene: synthesis and evaluation of their optical, redox and photovoltaic properties |
| title_sort | Push-pull heterocyclic dyes based on pyrrole and thiophene: synthesis and evaluation of their optical, redox and photovoltaic properties |
| topic | Heterocyclic push-pull dyes Thiophene Pyrrole Dye-sensitized solar cells Auxiliary donor/acceptor heterocycles Synthesis auxiliary donor acceptor heterocycles |
| topic_facet | Heterocyclic push-pull dyes Thiophene Pyrrole Dye-sensitized solar cells Auxiliary donor/acceptor heterocycles Synthesis auxiliary donor acceptor heterocycles |
| url | https://hdl.handle.net/1822/78288 |
| visible | 1 |