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Título: STRUCTURAL OPTIMIZATION OF BENZOTHIADIAZOLE DERIVATES AIMING HIGH EMISSIVITY AND AGGREGATION-INDUCED ENHANCED EMISSION
Autor: RAQUEL MAZZOLI DA ROCHA FIUZA
Colaborador(es): JONES LIMBERGER - Orientador
RICARDO QUEIROZ AUCELIO - Coorientador
Catalogação: 20/MAI/2021 Língua(s): PORTUGUESE - BRAZIL
Tipo: TEXT Subtipo: THESIS
Notas: [pt] Todos os dados constantes dos documentos são de inteira responsabilidade de seus autores. Os dados utilizados nas descrições dos documentos estão em conformidade com os sistemas da administração da PUC-Rio.
[en] All data contained in the documents are the sole responsibility of the authors. The data used in the descriptions of the documents are in conformity with the systems of the administration of PUC-Rio.
Referência(s): [pt] https://www.maxwell.vrac.puc-rio.br/projetosEspeciais/ETDs/consultas/conteudo.php?strSecao=resultado&nrSeq=52816&idi=1
[en] https://www.maxwell.vrac.puc-rio.br/projetosEspeciais/ETDs/consultas/conteudo.php?strSecao=resultado&nrSeq=52816&idi=2
DOI: https://doi.org/10.17771/PUCRio.acad.52816
Resumo:
The 2,1,3-benzothiadiazole (BTD) core derivatives are highly emissive and with recognized application in several areas of light technology (dye-sensitized solar cells, fluorescent probes, emitters devices such as OLEDs, etc.). BTD derivatives substituted with styrene group have been described as excellent fluorescent probes for protein conformations study. In addition, the LaSOQF research group has been producing new luminescent BTD derivatives and proposed different applications for them. Therefore, the objective of this work was to develop/optimize the synthesis of novel styryl-BTD derivatives. This design aimed at obtaining more luminescent compounds from the replacement of one of the styryl groups by 4-methoxyphenyl, 4-methoxyphenoxy or 2-biphenyl, seeking for intramolecular charge transfer (ICT) and also aggregated-induced enhanced emission (AIEE) characteristics. To obtain the desired compounds, brominated BTD derivatives were submitted to Heck reactions with styrene. Thus, the target fluorophores were obtained with yields ranging between 36 per cent and 87 per cent. Then, photophysical characterization of the fluorophores was carried out and absorption maxima between 404 and 450 nm and emission maxima between 503 and 578 nm were obtained, indicating the high stability of the excited state (delta lambda equal 90-121 nm). The determined values of [fi]FL (0.31-0.69) confirmed the high emissivity of the compounds. In addition, the compound 4-(4-methoxyphenoxy)-7-styrylbenzo[c] [1,2,5]thiadiazole showed of AIEE properties. The novel molecules developed are being applied as fluorescent probes for determination of water in commercial ethanolic solutions.
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