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A Novel Fluorescent Probe for Determination of pH and Viscosity Based on a Highly Water-Soluble 1,8-Naphthalimide Rotor

A novel highly water-soluble 1,8-naphthalimide with pH and viscosity-sensing fluorescence was synthesized and investigated. The synthesized compound was designed as a molecular device in which a molecular rotor and molecular “off-on” switcher were integrated. In order to obtain a TICT driven molecul...

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Autores principales: Bakov, Ventsislav V., Georgiev, Nikolai I., Bojinov, Vladimir B.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9657100/
https://www.ncbi.nlm.nih.gov/pubmed/36364383
http://dx.doi.org/10.3390/molecules27217556
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author Bakov, Ventsislav V.
Georgiev, Nikolai I.
Bojinov, Vladimir B.
author_facet Bakov, Ventsislav V.
Georgiev, Nikolai I.
Bojinov, Vladimir B.
author_sort Bakov, Ventsislav V.
collection PubMed
description A novel highly water-soluble 1,8-naphthalimide with pH and viscosity-sensing fluorescence was synthesized and investigated. The synthesized compound was designed as a molecular device in which a molecular rotor and molecular “off-on” switcher were integrated. In order to obtain a TICT driven molecular motion at C-4 position of the 1,8-naphthalimide fluorophore, a 4-methylpiperazinyl fragment was introduced. The molecular motion was confirmed after photophysical investigation in solvents with different viscosity; furthermore, the fluorescence-sensing properties of the examined compound were investigated in 100% aqueous medium and it was found that it could be used as an efficient fluorescent probe for pH. Due to the non-emissive deexcitation nature of the TICT fluorophore, the novel system showed low yellow–green emission, which represented “power-on”/“rotor-on” state. The protonation of the methylpiperazine amine destabilized the TICT process, which was accompanied by fluorescence enhancement indicating a “power-on”/“rotor-off” state of the system. The results obtained clearly illustrated the great potential of the synthesized compound to serve as pH- and viscosity-sensing material in aqueous solution.
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spelling pubmed-96571002022-11-15 A Novel Fluorescent Probe for Determination of pH and Viscosity Based on a Highly Water-Soluble 1,8-Naphthalimide Rotor Bakov, Ventsislav V. Georgiev, Nikolai I. Bojinov, Vladimir B. Molecules Article A novel highly water-soluble 1,8-naphthalimide with pH and viscosity-sensing fluorescence was synthesized and investigated. The synthesized compound was designed as a molecular device in which a molecular rotor and molecular “off-on” switcher were integrated. In order to obtain a TICT driven molecular motion at C-4 position of the 1,8-naphthalimide fluorophore, a 4-methylpiperazinyl fragment was introduced. The molecular motion was confirmed after photophysical investigation in solvents with different viscosity; furthermore, the fluorescence-sensing properties of the examined compound were investigated in 100% aqueous medium and it was found that it could be used as an efficient fluorescent probe for pH. Due to the non-emissive deexcitation nature of the TICT fluorophore, the novel system showed low yellow–green emission, which represented “power-on”/“rotor-on” state. The protonation of the methylpiperazine amine destabilized the TICT process, which was accompanied by fluorescence enhancement indicating a “power-on”/“rotor-off” state of the system. The results obtained clearly illustrated the great potential of the synthesized compound to serve as pH- and viscosity-sensing material in aqueous solution. MDPI 2022-11-04 /pmc/articles/PMC9657100/ /pubmed/36364383 http://dx.doi.org/10.3390/molecules27217556 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Bakov, Ventsislav V.
Georgiev, Nikolai I.
Bojinov, Vladimir B.
A Novel Fluorescent Probe for Determination of pH and Viscosity Based on a Highly Water-Soluble 1,8-Naphthalimide Rotor
title A Novel Fluorescent Probe for Determination of pH and Viscosity Based on a Highly Water-Soluble 1,8-Naphthalimide Rotor
title_full A Novel Fluorescent Probe for Determination of pH and Viscosity Based on a Highly Water-Soluble 1,8-Naphthalimide Rotor
title_fullStr A Novel Fluorescent Probe for Determination of pH and Viscosity Based on a Highly Water-Soluble 1,8-Naphthalimide Rotor
title_full_unstemmed A Novel Fluorescent Probe for Determination of pH and Viscosity Based on a Highly Water-Soluble 1,8-Naphthalimide Rotor
title_short A Novel Fluorescent Probe for Determination of pH and Viscosity Based on a Highly Water-Soluble 1,8-Naphthalimide Rotor
title_sort novel fluorescent probe for determination of ph and viscosity based on a highly water-soluble 1,8-naphthalimide rotor
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9657100/
https://www.ncbi.nlm.nih.gov/pubmed/36364383
http://dx.doi.org/10.3390/molecules27217556
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