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https://hdl.handle.net/1822/43863
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Campo DC | Valor | Idioma |
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dc.contributor.author | Castro, Maria Cidália Rodrigues | por |
dc.contributor.author | Belsley, M. | por |
dc.contributor.author | Raposo, M. Manuela M. | por |
dc.date.accessioned | 2016-12-26T22:13:34Z | - |
dc.date.issued | 2016-03 | - |
dc.identifier.citation | Castro, M. C. R., Belsley, M., & Raposo, M. M. M. (2016). Synthesis and characterization of push-pull bithienylpyrrole NLOphores with enhanced hyperpolarizabilities. Dyes and Pigments 131, 333-339. doi: 10.1016/j.dyepig.2016.04.027 | por |
dc.identifier.issn | 0143-7208 | por |
dc.identifier.uri | https://hdl.handle.net/1822/43863 | - |
dc.description.abstract | Novel pushepull second harmonic generation (SHG) chromophores 3-6 were synthesized in order to study how their optical properties are affected by an increase in the size of the p-bridge and also by connecting different electron accepting moieties (dicyanovinyl- and tricyanovinyl) to the (bi)thienylpyrrole system at position 5 of the pyrrole ring or at position 5 of the thiophene heterocycle. The precursor aldehydes were prepared through two different synthetic methodologies: Suzuki coupling (5ab) or Suzuki coupling followed by Vilsmeier formylation (2a-b). The final donor-acceptor systems 4-6 were prepared by tricyanovinylation reaction of precursors 1a-b or by Knoevenagel reaction of the precursor aldehydes 2b or 5b with malononitrile. Hyper-Rayleigh scattering in dioxane solutions using a fundamental wavelength of 1064 nm was employed to evaluate their second-order nonlinear optical properties. The experimental results showed that the optical properties are influenced by the electronacceptor strength of the groups, the length of the p-spacer/donor group as well as by the relative position of the pyrrole and thiophene heterocycles to the acceptor groups. The dicyanovinyl derivative 6b, which embodies the longer p-conjugated bridge functionalized in the thiophene ring, exhibited the largest first hyperpolarizability (b= 10,900x10 -30 esu, using the T convention) thus indicating its potential application as a SHG chromophore. As far as we are aware, this represents the largest hyperpolarizability reported to date for a bithienylpyrrole derivative. | por |
dc.description.sponsorship | The authors thank the Fundação para a Ciência e Tecnologia (Portugal) and FEDER-COMPETE for financial support through the Centro de Química Universidade do Minho, Projects PTDC/QUI/66251/2006 (FCOMP-01-0124-FEDER-007429), CQ/UM PEst-C/QUI/UI0686/2013 (FCOMP-01-0124-FEDER-037302) and a PhD grant to M. C. R. Castro (SFRH/BD/78037/2011). The NMR spectrometer Bruker Avance III 400 is part of the National NMR Network and was purchased within the framework of the National Program for Scientific Re-equipment, with funds from FCT. | por |
dc.language.iso | eng | por |
dc.publisher | Elsevier 1 | por |
dc.relation | info:eu-repo/grantAgreement/FCT/5876-PPCDTI/66251/PT | por |
dc.relation | info:eu-repo/grantAgreement/FCT/COMPETE/132953/PT | por |
dc.relation | info:eu-repo/grantAgreement/FCT/SFRH/SFRH%2FBD%2F78037%2F2011/PT | por |
dc.rights | restrictedAccess | por |
dc.subject | Knoevenagel condensation | por |
dc.subject | Push-pull (bi)thienylpyrroles | por |
dc.subject | Pyrrole | por |
dc.subject | Thiophene | por |
dc.subject | Auxiliary donor heterocycles | por |
dc.subject | First hyperpolarizability (beta) | por |
dc.subject | First hyperpolarizability (β) | por |
dc.title | Synthesis and characterization of push–pull bithienylpyrrole NLOphores with enhanced hyperpolarizabilities | por |
dc.type | article | por |
dc.peerreviewed | yes | por |
dc.relation.publisherversion | www.sciencedirect.com/science/article/pii/S0143720816301565 | por |
sdum.publicationstatus | info:eu-repo/semantics/publishedVersion | por |
oaire.citationStartPage | 333 | por |
oaire.citationEndPage | 339 | por |
oaire.citationTitle | Dyes and Pigments | por |
oaire.citationVolume | 131 | por |
dc.identifier.doi | 10.1016/j.dyepig.2016.04.027 | por |
dc.subject.fos | Ciências Naturais::Ciências Físicas | por |
dc.subject.fos | Ciências Naturais::Ciências Químicas | por |
dc.subject.wos | Science & Technology | por |
sdum.journal | Dyes and Pigments | por |
Aparece nas coleções: | CDF - FAMO - Artigos/Papers (with refereeing) CDQuim - Artigos (Papers) |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
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Dyes and Pigments 131 (2016) 333-339.pdf Acesso restrito! | 787,61 kB | Adobe PDF | Ver/Abrir |