Publicação
2-arylthienyl-substituted 1,3-benzothiazoles as new nonlinear optical chromophores
| Resumo: | A series of nonlinear optical chromophores 6 containing a substituted benzothiazole ring have been synthesized and characterized. 1,3-Benzothiazoles 6 were prepared by reacting various formyl derivatives of thienyl compounds with ortho-aminobenzenethiol in fair to excellent yields. These in turn were prepared by Suzuki coupling between aryl and thienyl precursors. The electronic interactions between donor and acceptor end groups in the conjugated 1,3-benzothiazoles 6 are expressed in the intense and markedly solvatochromic CT transitions. The solvatochromic behaviour of compounds 6 was determinated by linear regression analyses of absorption maxima in several solvents, whereby benzothiazole 6f was found to be a very appropriate indicator dye whose absorption wavenumbers (νmax= 1590 cm –1) in aliphatic and dipolar aprotic and in aromatic and chlorinated solvents excellently correlate with the π* values defined by Kamlet and Taft. Hyper-Rayleigh scattering was used to measure the first hyperpolarizabilities β of the mentioned compounds. Thermo gravimetric analysis (TGA) was used to evaluate their thermal stability. The experimental results indicate that good nonlinearity–thermal stability is well balanced for chromophores 6, making them good candidates for device applications. |
|---|---|
| Autores principais: | Costa, Susana P. G. |
| Outros Autores: | Batista, Rosa Maria Ferreira; Cardoso, Paulo; Belsley, M.; Raposo, M. Manuela M. |
| Assunto: | Arylthiophenes Bithiophenes Aldehydes Benzothiazoles Acceptor substituted oligothiophenes UV/Visible spectroscopy Chromophores Solvatochromism Thermal stability Nonlinear (NLO) optics Hyper-Rayleight Scattering Optical properties UV/Vis spectroscopy nonlinear optics |
| Ano: | 2006 |
| País: | Portugal |
| Tipo de documento: | artigo |
| Tipo de acesso: | acesso aberto |
| Instituição associada: | Universidade do Minho |
| Idioma: | inglês |
| Origem: | RepositóriUM - Universidade do Minho |
| _version_ | 1866877242694434816 |
|---|---|
| author | Costa, Susana P. G. |
| author2 | Batista, Rosa Maria Ferreira Cardoso, Paulo Belsley, M. Raposo, M. Manuela M. |
| author2_role | author author author author |
| author_facet | Costa, Susana P. G. Batista, Rosa Maria Ferreira Cardoso, Paulo Belsley, M. Raposo, M. Manuela M. |
| author_role | author |
| contributor_name_str_mv | Universidade do Minho |
| country_str | PT |
| creators_json_txt | [{\"Person.name\":\"Costa, Susana P. G.\"},{\"Person.name\":\"Batista, Rosa Maria Ferreira\"},{\"Person.name\":\"Cardoso, Paulo\"},{\"Person.name\":\"Belsley, M.\"},{\"Person.name\":\"Raposo, M. Manuela M.\"}] |
| datacite.contributors.contributor.contributorName.fl_str_mv | Universidade do Minho |
| datacite.creators.creator.creatorName.fl_str_mv | Costa, Susana P. G. Batista, Rosa Maria Ferreira Cardoso, Paulo Belsley, M. Raposo, M. Manuela M. |
| datacite.date.Accepted.fl_str_mv | 2006-01-01T00:00:00Z |
| datacite.date.available.fl_str_mv | 2008-05-21T17:39:04Z |
| datacite.date.embargoed.fl_str_mv | 2008-05-21T17:39:04Z |
| datacite.rights.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| datacite.subjects.subject.fl_str_mv | Arylthiophenes Bithiophenes Aldehydes Benzothiazoles Acceptor substituted oligothiophenes UV/Visible spectroscopy Chromophores Solvatochromism Thermal stability Nonlinear (NLO) optics Hyper-Rayleight Scattering Optical properties UV/Vis spectroscopy nonlinear optics |
| datacite.titles.title.fl_str_mv | 2-arylthienyl-substituted 1,3-benzothiazoles as new nonlinear optical chromophores |
| dc.contributor.none.fl_str_mv | Universidade do Minho |
| dc.creator.none.fl_str_mv | Costa, Susana P. G. Batista, Rosa Maria Ferreira Cardoso, Paulo Belsley, M. Raposo, M. Manuela M. |
| dc.date.Accepted.fl_str_mv | 2006-01-01T00:00:00Z |
| dc.date.available.fl_str_mv | 2008-05-21T17:39:04Z |
| dc.date.embargoed.fl_str_mv | 2008-05-21T17:39:04Z |
| dc.format.none.fl_str_mv | application/pdf |
| dc.identifier.none.fl_str_mv | https://hdl.handle.net/1822/7843 |
| dc.language.none.fl_str_mv | eng |
| dc.publisher.none.fl_str_mv | Wiley-VCH Verlag |
| dc.rights.none.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| dc.subject.none.fl_str_mv | Arylthiophenes Bithiophenes Aldehydes Benzothiazoles Acceptor substituted oligothiophenes UV/Visible spectroscopy Chromophores Solvatochromism Thermal stability Nonlinear (NLO) optics Hyper-Rayleight Scattering Optical properties UV/Vis spectroscopy nonlinear optics |
| dc.title.fl_str_mv | 2-arylthienyl-substituted 1,3-benzothiazoles as new nonlinear optical chromophores |
| dc.type.none.fl_str_mv | http://purl.org/coar/resource_type/c_6501 |
| description | A series of nonlinear optical chromophores 6 containing a substituted benzothiazole ring have been synthesized and characterized. 1,3-Benzothiazoles 6 were prepared by reacting various formyl derivatives of thienyl compounds with ortho-aminobenzenethiol in fair to excellent yields. These in turn were prepared by Suzuki coupling between aryl and thienyl precursors. The electronic interactions between donor and acceptor end groups in the conjugated 1,3-benzothiazoles 6 are expressed in the intense and markedly solvatochromic CT transitions. The solvatochromic behaviour of compounds 6 was determinated by linear regression analyses of absorption maxima in several solvents, whereby benzothiazole 6f was found to be a very appropriate indicator dye whose absorption wavenumbers (νmax= 1590 cm –1) in aliphatic and dipolar aprotic and in aromatic and chlorinated solvents excellently correlate with the π* values defined by Kamlet and Taft. Hyper-Rayleigh scattering was used to measure the first hyperpolarizabilities β of the mentioned compounds. Thermo gravimetric analysis (TGA) was used to evaluate their thermal stability. The experimental results indicate that good nonlinearity–thermal stability is well balanced for chromophores 6, making them good candidates for device applications. |
| dirty | 0 |
| eu_rights_str_mv | openAccess |
| format | article |
| fulltext.url.fl_str_mv | https://prod-dspace.uminho.pt/bitstreams/0cafc28a-3673-4939-8ca9-54ba7b25665a/download |
| id | rum_586bf10d8391dcbcbe24d2ca558848ec |
| identifier.url.fl_str_mv | https://hdl.handle.net/1822/7843 |
| 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:1822/7843 |
| organization_str_mv | urn:organizationAcronym:repositorium |
| person_str_mv | Costa, Susana P. G. Batista, Rosa Maria Ferreira Cardoso, Paulo Belsley, M. Raposo, M. Manuela M. |
| publishDate | 2006 |
| publisher.none.fl_str_mv | Wiley-VCH Verlag |
| reponame_str | RepositóriUM - Universidade do Minho |
| repository_id_str | urn:repositoryAcronym:rum |
| service_str_mv | urn:repositoryAcronym:rum |
| spelling | engWiley-VCH VerlagengA series of nonlinear optical chromophores 6 containing a substituted benzothiazole ring have been synthesized and characterized. 1,3-Benzothiazoles 6 were prepared by reacting various formyl derivatives of thienyl compounds with ortho-aminobenzenethiol in fair to excellent yields. These in turn were prepared by Suzuki coupling between aryl and thienyl precursors. The electronic interactions between donor and acceptor end groups in the conjugated 1,3-benzothiazoles 6 are expressed in the intense and markedly solvatochromic CT transitions. The solvatochromic behaviour of compounds 6 was determinated by linear regression analyses of absorption maxima in several solvents, whereby benzothiazole 6f was found to be a very appropriate indicator dye whose absorption wavenumbers (νmax= 1590 cm –1) in aliphatic and dipolar aprotic and in aromatic and chlorinated solvents excellently correlate with the π* values defined by Kamlet and Taft. Hyper-Rayleigh scattering was used to measure the first hyperpolarizabilities β of the mentioned compounds. Thermo gravimetric analysis (TGA) was used to evaluate their thermal stability. The experimental results indicate that good nonlinearity–thermal stability is well balanced for chromophores 6, making them good candidates for device applications.application/pdfeng2-arylthienyl-substituted 1,3-benzothiazoles as new nonlinear optical chromophoresCosta, Susana P. G.Batista, Rosa Maria FerreiraCardoso, PauloBelsley, M.Raposo, M. Manuela M.HostingInstitutionOrganizationalUniversidade do Minhoe-mailmailto:repositorium@usdb.uminho.ptrepositorium@usdb.uminho.ptISSNIsPartOf1434-193XDOIIsPartOf10.1002/ejoc.2006000592008-05-21T17:39:04Z200620062006-01-01T00:00:00ZHandlehttps://hdl.handle.net/1822/7843http://purl.org/coar/access_right/c_abf2open accessArylthiophenesBithiophenesAldehydesBenzothiazolesAcceptor substituted oligothiophenesUV/Visible spectroscopyChromophoresSolvatochromismThermal stabilityNonlinear (NLO) opticsHyper-Rayleight ScatteringOptical propertiesUV/Vis spectroscopynonlinear optics227563 bytesliteraturehttp://purl.org/coar/resource_type/c_6501journal articlehttp://purl.org/coar/access_right/c_abf2application/pdffulltexthttps://prod-dspace.uminho.pt/bitstreams/0cafc28a-3673-4939-8ca9-54ba7b25665a/download |
| spellingShingle | 2-arylthienyl-substituted 1,3-benzothiazoles as new nonlinear optical chromophores Costa, Susana P. G. Arylthiophenes Bithiophenes Aldehydes Benzothiazoles Acceptor substituted oligothiophenes UV/Visible spectroscopy Chromophores Solvatochromism Thermal stability Nonlinear (NLO) optics Hyper-Rayleight Scattering Optical properties UV/Vis spectroscopy nonlinear optics |
| status | SINGLETON |
| subject.fl_str_mv | Arylthiophenes Bithiophenes Aldehydes Benzothiazoles Acceptor substituted oligothiophenes UV/Visible spectroscopy Chromophores Solvatochromism Thermal stability Nonlinear (NLO) optics Hyper-Rayleight Scattering Optical properties UV/Vis spectroscopy nonlinear optics |
| title | 2-arylthienyl-substituted 1,3-benzothiazoles as new nonlinear optical chromophores |
| title_full | 2-arylthienyl-substituted 1,3-benzothiazoles as new nonlinear optical chromophores |
| title_fullStr | 2-arylthienyl-substituted 1,3-benzothiazoles as new nonlinear optical chromophores |
| title_full_unstemmed | 2-arylthienyl-substituted 1,3-benzothiazoles as new nonlinear optical chromophores |
| title_short | 2-arylthienyl-substituted 1,3-benzothiazoles as new nonlinear optical chromophores |
| title_sort | 2-arylthienyl-substituted 1,3-benzothiazoles as new nonlinear optical chromophores |
| topic | Arylthiophenes Bithiophenes Aldehydes Benzothiazoles Acceptor substituted oligothiophenes UV/Visible spectroscopy Chromophores Solvatochromism Thermal stability Nonlinear (NLO) optics Hyper-Rayleight Scattering Optical properties UV/Vis spectroscopy nonlinear optics |
| topic_facet | Arylthiophenes Bithiophenes Aldehydes Benzothiazoles Acceptor substituted oligothiophenes UV/Visible spectroscopy Chromophores Solvatochromism Thermal stability Nonlinear (NLO) optics Hyper-Rayleight Scattering Optical properties UV/Vis spectroscopy nonlinear optics |
| url | https://hdl.handle.net/1822/7843 |
| visible | 1 |