Abstract
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.
Highlights
Naphthalimide derivatives are of interest due to their promising properties such as strong emission, high quantum efficiency, good photostability, thermal stability, filmforming ability, etc. [1–5]
When water was added in the dioxane solutions, the emission intensity of solution was rapidly quenched
The quenching effect on emission intensity was observed in polar solvents, but for higher water levels
Summary
Naphthalimide derivatives are of interest due to their promising properties such as strong emission, high quantum efficiency, good photostability, thermal stability, filmforming ability, etc. [1–5]. Naphthalimide derivatives are of interest due to their promising properties such as strong emission, high quantum efficiency, good photostability, thermal stability, filmforming ability, etc. The optical and photophysical properties of naphthalimide derivatives depend on the substituent nature of the heterocycle as well as the position of the substituents [2,17]. The chemical modification of the naphthalimide structure mainly on the imide N site or at the position 4 of the naphthalene moiety gives the possibility to tune their absorption and emission parameters. The photophysical properties of the naphthalimide derivatives can be tuned by the appropriate choice of the push-pull substituents at imide nitrogen and C4 position at naphthalene ring due to the intramolecular charge transfer in this system [18,20,21]
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