Publicação
Synthesis and characterization of push-pull bithiophene and thieno[3,2-b]thiophene derivatives bearing an ethyne linker as sensitizers for dye-sensitized solar cells
| Resumo: | Five push-pull heterocyclic dyes 4-7, and 9 were synthesized and characterized in order to study the variations in the optical, electronic and photovoltaic properties induced by structural modifications, i.e. different spacer units and anchoring groups. The final push-pull conjugated dyes 6-7 and 9 are formed by a N,N-dimethylaniline donor moiety conjugated with bithiophene, ethynyl-bithiophene or ethynyl-thieno[3,2-b]thiophene spacers and cyanoacetic acid or rhodanine-3-acetic acid as anchoring group. The synthesis of the precursor aldehydes 4-5 was accomplished through a Sonogashira coupling, on the other hand, compound 8 was prepared by Suzuki coupling. Knoevenagel condensation of aldehydes 4, 5 and 8 with cyanoacetic acid or rhodamine-3-acetic acid afforded the final push-pull dyes 6, 7 and 9. Information on conformation, electronic structure and electron distribution was obtained by DFT and TDDFTcalculations. This multidisciplinary study regarding the evaluation of the optical, redox and photovoltaic properties of the dyes reveals that compound 7, bearing an ethynyl-bithiophene spacer conjugated with a cyanoacetic acid anchoring group, has the highest conversion efficiency (3.51 %) as dye sensitizer in nanocrystalline TiO2 solar cells. Co-adsorption studies were also performed for dyes 6-7 with N719 as co-adsorbent, and this enhanced dye efficiencies by 33-45 %. The best cell performance was obtained by co-adsorbing N719 and dye 7 (75/25 vol%) with 4.66 % efficiency. |
|---|---|
| Autores principais: | Fernandes, Sara Sofia Marques |
| Outros Autores: | Mesquita, I.; Andrade, L.; Mendes, A.; Justino, Licinia L. G.; Burrows, H. D.; Raposo, M. Manuela M. |
| Assunto: | Dye sensitized solar cells Metal-free organic dyes Bithiophene Thieno[3,2-b]thiophene Cyanoacetic acid Rhodanine-3-acetic acid Co-adsorption |
| Ano: | 2017 |
| País: | Portugal |
| Tipo de documento: | artigo |
| Tipo de acesso: | acesso aberto |
| Instituição associada: | Universidade do Minho |
| Idioma: | inglês |
| Origem: | RepositóriUM - Universidade do Minho |
| _version_ | 1866876074074308608 |
|---|---|
| author | Fernandes, Sara Sofia Marques |
| author2 | Mesquita, I. Andrade, L. Mendes, A. Justino, Licinia L. G. Burrows, H. D. Raposo, M. Manuela M. |
| author2_role | author author author author author author |
| author_facet | Fernandes, Sara Sofia Marques Mesquita, I. Andrade, L. Mendes, A. Justino, Licinia L. G. Burrows, H. D. 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\":\"Mesquita, I.\"},{\"Person.name\":\"Andrade, L.\"},{\"Person.name\":\"Mendes, A.\"},{\"Person.name\":\"Justino, Licinia L. G.\"},{\"Person.name\":\"Burrows, H. D.\"},{\"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 Mesquita, I. Andrade, L. Mendes, A. Justino, Licinia L. G. Burrows, H. D. Raposo, M. Manuela M. |
| datacite.date.Accepted.fl_str_mv | 2017-01-01T00:00:00Z |
| datacite.rights.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| datacite.subjects.subject.fl_str_mv | Dye sensitized solar cells Metal-free organic dyes Bithiophene Thieno[3,2-b]thiophene Cyanoacetic acid Rhodanine-3-acetic acid Co-adsorption |
| datacite.titles.title.fl_str_mv | Synthesis and characterization of push-pull bithiophene and thieno[3,2-b]thiophene derivatives bearing an ethyne linker as sensitizers for dye-sensitized solar cells |
| dc.contributor.none.fl_str_mv | Universidade do Minho |
| dc.creator.none.fl_str_mv | Fernandes, Sara Sofia Marques Mesquita, I. Andrade, L. Mendes, A. Justino, Licinia L. G. Burrows, H. D. Raposo, M. Manuela M. |
| dc.date.Accepted.fl_str_mv | 2017-01-01T00:00:00Z |
| dc.format.none.fl_str_mv | application/pdf |
| dc.identifier.none.fl_str_mv | https://hdl.handle.net/1822/48399 |
| dc.language.none.fl_str_mv | eng |
| dc.publisher.none.fl_str_mv | Elsevier |
| dc.rights.none.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| dc.subject.none.fl_str_mv | Dye sensitized solar cells Metal-free organic dyes Bithiophene Thieno[3,2-b]thiophene Cyanoacetic acid Rhodanine-3-acetic acid Co-adsorption |
| dc.title.fl_str_mv | Synthesis and characterization of push-pull bithiophene and thieno[3,2-b]thiophene derivatives bearing an ethyne linker as sensitizers for dye-sensitized solar cells |
| dc.type.none.fl_str_mv | http://purl.org/coar/resource_type/c_6501 |
| description | Five push-pull heterocyclic dyes 4-7, and 9 were synthesized and characterized in order to study the variations in the optical, electronic and photovoltaic properties induced by structural modifications, i.e. different spacer units and anchoring groups. The final push-pull conjugated dyes 6-7 and 9 are formed by a N,N-dimethylaniline donor moiety conjugated with bithiophene, ethynyl-bithiophene or ethynyl-thieno[3,2-b]thiophene spacers and cyanoacetic acid or rhodanine-3-acetic acid as anchoring group. The synthesis of the precursor aldehydes 4-5 was accomplished through a Sonogashira coupling, on the other hand, compound 8 was prepared by Suzuki coupling. Knoevenagel condensation of aldehydes 4, 5 and 8 with cyanoacetic acid or rhodamine-3-acetic acid afforded the final push-pull dyes 6, 7 and 9. Information on conformation, electronic structure and electron distribution was obtained by DFT and TDDFTcalculations. This multidisciplinary study regarding the evaluation of the optical, redox and photovoltaic properties of the dyes reveals that compound 7, bearing an ethynyl-bithiophene spacer conjugated with a cyanoacetic acid anchoring group, has the highest conversion efficiency (3.51 %) as dye sensitizer in nanocrystalline TiO2 solar cells. Co-adsorption studies were also performed for dyes 6-7 with N719 as co-adsorbent, and this enhanced dye efficiencies by 33-45 %. The best cell performance was obtained by co-adsorbing N719 and dye 7 (75/25 vol%) with 4.66 % efficiency. |
| dirty | 0 |
| eu_rights_str_mv | openAccess |
| format | article |
| fulltext.url.fl_str_mv | https://prod-dspace.uminho.pt/bitstreams/38604732-5e87-4f94-885d-ad5028a65305/download |
| id | rum_85ce15668e02fc0f0902ffa2d35ee954 |
| identifier.url.fl_str_mv | https://hdl.handle.net/1822/48399 |
| 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:1822/48399 |
| organization_str_mv | urn:organizationAcronym:repositorium |
| person_str_mv | Fernandes, Sara Sofia Marques Mesquita, I. Andrade, L. Mendes, A. Justino, Licinia L. G. Burrows, H. D. Raposo, M. Manuela M. |
| publishDate | 2017 |
| publisher.none.fl_str_mv | Elsevier |
| reponame_str | RepositóriUM - Universidade do Minho |
| repository_id_str | urn:repositoryAcronym:rum |
| service_str_mv | urn:repositoryAcronym:rum |
| spelling | engElsevierporFive push-pull heterocyclic dyes 4-7, and 9 were synthesized and characterized in order to study the variations in the optical, electronic and photovoltaic properties induced by structural modifications, i.e. different spacer units and anchoring groups. The final push-pull conjugated dyes 6-7 and 9 are formed by a N,N-dimethylaniline donor moiety conjugated with bithiophene, ethynyl-bithiophene or ethynyl-thieno[3,2-b]thiophene spacers and cyanoacetic acid or rhodanine-3-acetic acid as anchoring group. The synthesis of the precursor aldehydes 4-5 was accomplished through a Sonogashira coupling, on the other hand, compound 8 was prepared by Suzuki coupling. Knoevenagel condensation of aldehydes 4, 5 and 8 with cyanoacetic acid or rhodamine-3-acetic acid afforded the final push-pull dyes 6, 7 and 9. Information on conformation, electronic structure and electron distribution was obtained by DFT and TDDFTcalculations. This multidisciplinary study regarding the evaluation of the optical, redox and photovoltaic properties of the dyes reveals that compound 7, bearing an ethynyl-bithiophene spacer conjugated with a cyanoacetic acid anchoring group, has the highest conversion efficiency (3.51 %) as dye sensitizer in nanocrystalline TiO2 solar cells. Co-adsorption studies were also performed for dyes 6-7 with N719 as co-adsorbent, and this enhanced dye efficiencies by 33-45 %. The best cell performance was obtained by co-adsorbing N719 and dye 7 (75/25 vol%) with 4.66 % efficiency.application/pdfporSynthesis and characterization of push-pull bithiophene and thieno[3,2-b]thiophene derivatives bearing an ethyne linker as sensitizers for dye-sensitized solar cellsFernandes, Sara Sofia MarquesMesquita, I.Andrade, L.Mendes, A.Justino, Licinia L. G.Burrows, H. D.Raposo, M. Manuela M.HostingInstitutionOrganizationalUniversidade do Minhoe-mailmailto:repositorium@usdb.uminho.ptrepositorium@usdb.uminho.ptISSNIsPartOf1566-1199DOIIsPartOf10.1016/j.orgel.2017.06.048201720172017-01-01T00:00:00ZHandlehttps://hdl.handle.net/1822/48399http://purl.org/coar/access_right/c_abf2open accessDye sensitized solar cellsMetal-free organic dyesBithiopheneThieno[3,2-b]thiopheneCyanoacetic acidRhodanine-3-acetic acidCo-adsorption2292378 bytesliteraturehttp://purl.org/coar/resource_type/c_6501journal articlehttp://purl.org/coar/access_right/c_abf2application/pdffulltexthttps://prod-dspace.uminho.pt/bitstreams/38604732-5e87-4f94-885d-ad5028a65305/download |
| spellingShingle | Synthesis and characterization of push-pull bithiophene and thieno[3,2-b]thiophene derivatives bearing an ethyne linker as sensitizers for dye-sensitized solar cells Fernandes, Sara Sofia Marques Dye sensitized solar cells Metal-free organic dyes Bithiophene Thieno[3,2-b]thiophene Cyanoacetic acid Rhodanine-3-acetic acid Co-adsorption |
| status | SINGLETON |
| subject.fl_str_mv | Dye sensitized solar cells Metal-free organic dyes Bithiophene Thieno[3,2-b]thiophene Cyanoacetic acid Rhodanine-3-acetic acid Co-adsorption |
| title | Synthesis and characterization of push-pull bithiophene and thieno[3,2-b]thiophene derivatives bearing an ethyne linker as sensitizers for dye-sensitized solar cells |
| title_full | Synthesis and characterization of push-pull bithiophene and thieno[3,2-b]thiophene derivatives bearing an ethyne linker as sensitizers for dye-sensitized solar cells |
| title_fullStr | Synthesis and characterization of push-pull bithiophene and thieno[3,2-b]thiophene derivatives bearing an ethyne linker as sensitizers for dye-sensitized solar cells |
| title_full_unstemmed | Synthesis and characterization of push-pull bithiophene and thieno[3,2-b]thiophene derivatives bearing an ethyne linker as sensitizers for dye-sensitized solar cells |
| title_short | Synthesis and characterization of push-pull bithiophene and thieno[3,2-b]thiophene derivatives bearing an ethyne linker as sensitizers for dye-sensitized solar cells |
| title_sort | Synthesis and characterization of push-pull bithiophene and thieno[3,2-b]thiophene derivatives bearing an ethyne linker as sensitizers for dye-sensitized solar cells |
| topic | Dye sensitized solar cells Metal-free organic dyes Bithiophene Thieno[3,2-b]thiophene Cyanoacetic acid Rhodanine-3-acetic acid Co-adsorption |
| topic_facet | Dye sensitized solar cells Metal-free organic dyes Bithiophene Thieno[3,2-b]thiophene Cyanoacetic acid Rhodanine-3-acetic acid Co-adsorption |
| url | https://hdl.handle.net/1822/48399 |
| visible | 1 |