Synthesis and Solvent Dependent Fluorescence of Some Piperidine-Substituted Naphthalimide Derivatives and Consequences for Water Sensing

Novel fluorescent strigolactone derivatives that contain the piperidine-substituted 1,8-naphthalimide ring system connected through an ether link to a bioactive 3-methyl-furan-2-one unit were synthesized and their spectroscopic properties investigated. The solvatochromic behavior of these piperidine...

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Main Authors: Radu Tigoianu, Anton Airinei, Emilian Georgescu, Alina Nicolescu, Florentina Georgescu, Dragos Lucian Isac, Calin Deleanu, Florin Oancea
Format: Article
Language:English
Published: MDPI AG 2022-03-01
Series:International Journal of Molecular Sciences
Subjects:
Online Access:https://www.mdpi.com/1422-0067/23/5/2760
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author Radu Tigoianu
Anton Airinei
Emilian Georgescu
Alina Nicolescu
Florentina Georgescu
Dragos Lucian Isac
Calin Deleanu
Florin Oancea
author_facet Radu Tigoianu
Anton Airinei
Emilian Georgescu
Alina Nicolescu
Florentina Georgescu
Dragos Lucian Isac
Calin Deleanu
Florin Oancea
author_sort Radu Tigoianu
collection DOAJ
description Novel fluorescent strigolactone derivatives that contain the piperidine-substituted 1,8-naphthalimide ring system connected through an ether link to a bioactive 3-methyl-furan-2-one unit were synthesized and their spectroscopic properties investigated. The solvatochromic behavior of these piperidine-naphthalimides was monitored in solvents of different polarity using the electronic absorption and fluorescence spectra. These compounds exhibited a strong positive solvatochromism taking into account the change of solvent polarity, and the response mechanism was analyzed by fluorescence lifetime measurements. According to Catalan and [f(n), f(ε), β, α] solvent scales, the dipolarity and polarizability are relevant to describe the solute–solvent interactions. The emission chemosensing activity was discussed in order to determine the water content in organic environments. The emission intensity of these compounds decreased rapidly in dioxane, increasing water level up to 10%. Measuring of quantum yield indicated that the highest values of quantum efficiency were obtained in nonpolar solvents, while in polar solvents these derivatives revealed the lowest quantum yield. The fluorescence decay can be described by a monoexponential model for low water levels, and for higher water contents a biexponential model was valid.
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spelling doaj.art-3a78ad82b5ce47c28b4a990b4c6ac82e2023-11-23T23:09:11ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672022-03-01235276010.3390/ijms23052760Synthesis and Solvent Dependent Fluorescence of Some Piperidine-Substituted Naphthalimide Derivatives and Consequences for Water SensingRadu Tigoianu0Anton Airinei1Emilian Georgescu2Alina Nicolescu3Florentina Georgescu4Dragos Lucian Isac5Calin Deleanu6Florin Oancea7Petru Poni Institute of Macromolecular Chemistry, Romanian Academy, Aleea Grigore Ghica Voda 41A, 700487 Iasi, RomaniaPetru Poni Institute of Macromolecular Chemistry, Romanian Academy, Aleea Grigore Ghica Voda 41A, 700487 Iasi, RomaniaC. D. Nenitescu Centre of Organic Chemistry, Romanian Academy, Splaiul Independentei 202B, 060023 Bucharest, RomaniaPetru Poni Institute of Macromolecular Chemistry, Romanian Academy, Aleea Grigore Ghica Voda 41A, 700487 Iasi, RomaniaEnpro Soctech Com Srl, Str. Elefterie 51, 050524 Bucharest, RomaniaPetru Poni Institute of Macromolecular Chemistry, Romanian Academy, Aleea Grigore Ghica Voda 41A, 700487 Iasi, RomaniaPetru Poni Institute of Macromolecular Chemistry, Romanian Academy, Aleea Grigore Ghica Voda 41A, 700487 Iasi, RomaniaNational Research and Development Institute for Chemistry and Petrochemistry—ICECHIM, Splaiul Independentei 202B, 060023 Bucharest, RomaniaNovel fluorescent strigolactone derivatives that contain the piperidine-substituted 1,8-naphthalimide ring system connected through an ether link to a bioactive 3-methyl-furan-2-one unit were synthesized and their spectroscopic properties investigated. The solvatochromic behavior of these piperidine-naphthalimides was monitored in solvents of different polarity using the electronic absorption and fluorescence spectra. These compounds exhibited a strong positive solvatochromism taking into account the change of solvent polarity, and the response mechanism was analyzed by fluorescence lifetime measurements. According to Catalan and [f(n), f(ε), β, α] solvent scales, the dipolarity and polarizability are relevant to describe the solute–solvent interactions. The emission chemosensing activity was discussed in order to determine the water content in organic environments. The emission intensity of these compounds decreased rapidly in dioxane, increasing water level up to 10%. Measuring of quantum yield indicated that the highest values of quantum efficiency were obtained in nonpolar solvents, while in polar solvents these derivatives revealed the lowest quantum yield. The fluorescence decay can be described by a monoexponential model for low water levels, and for higher water contents a biexponential model was valid.https://www.mdpi.com/1422-0067/23/5/2760piperidine-1,8-naphthalimidesolvatochromismsolvent dependent emissionwater sensorfluorescence lifetime
spellingShingle Radu Tigoianu
Anton Airinei
Emilian Georgescu
Alina Nicolescu
Florentina Georgescu
Dragos Lucian Isac
Calin Deleanu
Florin Oancea
Synthesis and Solvent Dependent Fluorescence of Some Piperidine-Substituted Naphthalimide Derivatives and Consequences for Water Sensing
International Journal of Molecular Sciences
piperidine-1,8-naphthalimide
solvatochromism
solvent dependent emission
water sensor
fluorescence lifetime
title Synthesis and Solvent Dependent Fluorescence of Some Piperidine-Substituted Naphthalimide Derivatives and Consequences for Water Sensing
title_full Synthesis and Solvent Dependent Fluorescence of Some Piperidine-Substituted Naphthalimide Derivatives and Consequences for Water Sensing
title_fullStr Synthesis and Solvent Dependent Fluorescence of Some Piperidine-Substituted Naphthalimide Derivatives and Consequences for Water Sensing
title_full_unstemmed Synthesis and Solvent Dependent Fluorescence of Some Piperidine-Substituted Naphthalimide Derivatives and Consequences for Water Sensing
title_short Synthesis and Solvent Dependent Fluorescence of Some Piperidine-Substituted Naphthalimide Derivatives and Consequences for Water Sensing
title_sort synthesis and solvent dependent fluorescence of some piperidine substituted naphthalimide derivatives and consequences for water sensing
topic piperidine-1,8-naphthalimide
solvatochromism
solvent dependent emission
water sensor
fluorescence lifetime
url https://www.mdpi.com/1422-0067/23/5/2760
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