Engineering the BASHY Dye Platform toward Architectures with Responsive Fluorescence
A set of nine boronic-acid-derived salicylidenehydrazone (BASHY) complexes has been synthesized in good to very good chemical yields in a versatile three-component reaction. In an extension to previous reports on this dye platform, the focus was put on the electronic modification of the “vertical” p...
| Authors: | ; ; ; ; ; ; ; ; ; ; |
|---|---|
| Format: | Article |
| Publication date: | 2023 |
| Country: | España |
| Institution: | Universidad de Huelva (UHU) |
| Repository: | Arias Montano. Repositorio Institucional de la Universidad de Huelva |
| Language: | English |
| OAI Identifier: | oai:ariasmontano.uhu.es:10272/22934 |
| Online Access: | https://hdl.handle.net/10272/22934 |
| Access Level: | Open access |
| Keyword: | Fluorescence Photoinduced Electron Transfer Bioimaging Bashy dyes NIR region 2306.91 Química Orgánica. Análisis Instrumental |
| _version_ | 1878740283097612288 |
|---|---|
| author | Felicidade, João |
| author2 | F. Santos, Fabio M. Fernández Arteaga, Jesús Remón Ruiz, Patricia Campos-González, René Nguyen, Ha-Chi Nájera, Francisco Boscá, Francisco Ng, David Y. W. P. Gois, Pedro M. Pischel, Uwe |
| author2_role | author author author author author author author author author author |
| author_browse | Boscá, Francisco Campos-González, René F. Santos, Fabio M. Felicidade, João Fernández Arteaga, Jesús Ng, David Y. W. Nguyen, Ha-Chi Nájera, Francisco P. Gois, Pedro M. Pischel, Uwe Remón Ruiz, Patricia |
| author_facet | Felicidade, João F. Santos, Fabio M. Fernández Arteaga, Jesús Remón Ruiz, Patricia Campos-González, René Nguyen, Ha-Chi Nájera, Francisco Boscá, Francisco Ng, David Y. W. P. Gois, Pedro M. Pischel, Uwe |
| author_role | author |
| collection | Arias Montano. Repositorio Institucional de la Universidad de Huelva |
| description | A set of nine boronic-acid-derived salicylidenehydrazone (BASHY) complexes has been synthesized in good to very good chemical yields in a versatile three-component reaction. In an extension to previous reports on this dye platform, the focus was put on the electronic modification of the “vertical” positions of the salicylidenehydrazone backbone. This enabled the observation of fluorescence quenching by photoinduced electron transfer (PeT), which can be reverted by the addition of acid in organic solvent (OFF-ON fluorescence switching). The resulting emission is observed in the green-to-orange spectral region (maxima at 520–590 nm). In contrast, under physiological pH conditions in water, the PeT process is inherently decativated, thereby enabling the observation of fluorescence in the red-to-NIR region (maxima at 650–680 nm) with appreciable quantum yields and lifetimes. The latter characteristic supported the application of the dyes in fluorescence lifetime imaging (FLIM) of live A549 cells. |
| eu_rights_str_mv | openAccess |
| format | article |
| id | ES_d04e9ae8c8e779e4cffe73812276b452 |
| institution | Universidad de Huelva (UHU) |
| instname_str | Universidad de Huelva (UHU) |
| language | eng |
| network_acronym_str | ES |
| network_name_str | España |
| oai_identifier_str | oai:ariasmontano.uhu.es:10272/22934 |
| publishDate | 2023 |
| publishDateSort | 2023 |
| publisher | Wiley |
| publisherStr | Wiley |
| reponame_str | Arias Montano. Repositorio Institucional de la Universidad de Huelva |
| spelling | Engineering the BASHY Dye Platform toward Architectures with Responsive Fluorescence Felicidade, João F. Santos, Fabio M. Fernández Arteaga, Jesús Remón Ruiz, Patricia Campos-González, René Nguyen, Ha-Chi Nájera, Francisco Boscá, Francisco Ng, David Y. W. P. Gois, Pedro M. Pischel, Uwe Fluorescence Photoinduced Electron Transfer Bioimaging Bashy dyes NIR region 2306.91 Química Orgánica. Análisis Instrumental A set of nine boronic-acid-derived salicylidenehydrazone (BASHY) complexes has been synthesized in good to very good chemical yields in a versatile three-component reaction. In an extension to previous reports on this dye platform, the focus was put on the electronic modification of the “vertical” positions of the salicylidenehydrazone backbone. This enabled the observation of fluorescence quenching by photoinduced electron transfer (PeT), which can be reverted by the addition of acid in organic solvent (OFF-ON fluorescence switching). The resulting emission is observed in the green-to-orange spectral region (maxima at 520–590 nm). In contrast, under physiological pH conditions in water, the PeT process is inherently decativated, thereby enabling the observation of fluorescence in the red-to-NIR region (maxima at 650–680 nm) with appreciable quantum yields and lifetimes. The latter characteristic supported the application of the dyes in fluorescence lifetime imaging (FLIM) of live A549 cells. Wiley https://hdl.handle.net/10272/22934 |
| spellingShingle | Engineering the BASHY Dye Platform toward Architectures with Responsive Fluorescence Felicidade, João Fluorescence Photoinduced Electron Transfer Bioimaging Bashy dyes NIR region 2306.91 Química Orgánica. Análisis Instrumental |
| title | Engineering the BASHY Dye Platform toward Architectures with Responsive Fluorescence |
| title_full | Engineering the BASHY Dye Platform toward Architectures with Responsive Fluorescence |
| title_fullStr | Engineering the BASHY Dye Platform toward Architectures with Responsive Fluorescence |
| title_full_unstemmed | Engineering the BASHY Dye Platform toward Architectures with Responsive Fluorescence |
| title_short | Engineering the BASHY Dye Platform toward Architectures with Responsive Fluorescence |
| title_sort | Engineering the BASHY Dye Platform toward Architectures with Responsive Fluorescence |
| topic | Fluorescence Photoinduced Electron Transfer Bioimaging Bashy dyes NIR region 2306.91 Química Orgánica. Análisis Instrumental |
| topic_facet | Fluorescence Photoinduced Electron Transfer Bioimaging Bashy dyes NIR region 2306.91 Química Orgánica. Análisis Instrumental |
| url | https://hdl.handle.net/10272/22934 |