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

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

Content Provider	Europe PMC
Author	Bakov, Ventsislav V. Georgiev, Nikolai I. Bojinov, Vladimir B.
Editor	Viscardi, Guido Fin, Andrea
Copyright Year	2022
Abstract	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.
Journal	Molecules
Volume Number	27
DOI	10.3390/molecules27217556
PubMed Central reference number	PMC9657100
Issue Number	21
PubMed reference number	36364383
e-ISSN	14203049
Language	English
Publisher	Molecular Diversity Preservation International (MDPI)
Publisher Date	2022-11-04
Access Restriction	Open
Subject Keyword	1,8-naphthalimide twisted intramolecular charge transfer (TICT) fluorescence pH viscosity
Content Type	Text
Resource Type	Article
Subject	Physical and Theoretical Chemistry Medicine Chemistry Drug Discovery Pharmaceutical Science Analytical Chemistry Molecular Medicine Organic Chemistry

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