Synthesis, structural analysis and application of a series of solid-state fluorochromes—aryl hydrazones of 4-hydrazino-N-hexyl-1,8-naphthalimide

Ivanov, Ivaylo P.; Dimitrova, Mashenka; Tasheva, Donka; Cheshmedzhieva, Diana; Lozanov, Valentin; Ilieva, Sylvia

doi:10.1016/j.tet.2012.10.093

Cited by 7 publications

(4 citation statements)

References 40 publications

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“…The aim of the present study is to compute the spectral characteristics of the newly synthesized hydrazones 14 by quantum chemical methods and on the comparative basis between theoretical results and experimental spectra to establish correlation dependences of spectral properties with structural indices. From a theoretical point of view, it is valuable to use a computational design to predict the substituent effect on the spectral properties of the derivatives before synthesizing substrates for fluorescent histochemical localization of the enzyme activity.…”

Section: Introductionmentioning

confidence: 99%

“…The studied hydrazones, presented in Scheme 1, were synthesized in our laboratory. 14 To assess the capacity of the applied functionals in predicting the electronic transitions, a comparison is made between experimental absorption and fluorescence spectra and calculated excitation energies, fluorescence energies, Stokes shifts. Experimental and theoretically calculated absorption and emission spectral characteristics were rationalized in terms of various electronic indices: s p and s + p Hammett substituent constants, 25 electrostatic potential at nuclei (EPN), 26,27 and Hirshfeld atomic charges.…”

Section: Introductionmentioning

confidence: 99%

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Experimental and theoretical study on the absorption and fluorescence properties of substituted aryl hydrazones of 1,8-naphthalimide

Cheshmedzhieva

Ivanova

Stoyanov

et al. 2011

Phys. Chem. Chem. Phys.

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Absorption and fluorescence spectra in acetonitrile for a series of substituted aryl hydrazones of N-hexyl-1,8-naphthalimide are studied with the aim of potential application of the compounds for enzyme activity localization. The influence of the substituents on the spectral characteristics has been evaluated. The absorption and fluorescence energies of substituted aryl-1,8-naphthalimide hydrazones have been calculated with the PCM TDDFT formalism. The M06 and PBE0 functionals, combined with the 6-31+G(d) atomic basis set, have been found to accurately model the excited state properties of the present set of solvated fluorophores. Absorption and fluorescence spectral characteristics have been rationalized in terms of experimental and theoretical electronic indices in order to assess their predictive abilities for application in designing analogues with good emitting properties. An excellent linear dependence is established between the experimental fluorescence and Hammett σ(p)(+) substituent constants and on the other hand σ(p)(+) constants correlate with the theoretically calculated values for the electrostatic potential at nuclei (EPN). A model for predicting the fluorescence properties of substituted hydrazones by means of EPN is drawn, including the polysubstituted derivatives, where Hammett constants are not applicable.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Experimental and theoretical study on the absorption and fluorescence properties of substituted aryl hydrazones of 1,8-naphthalimide

Cheshmedzhieva

Ivanova

Stoyanov

et al. 2011

Phys. Chem. Chem. Phys.

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“…On the contrary, it was not fluorescence with electron-withdrawing group attached (-NO 2 ). Detailed analysis of the electronic effects of substituents on the physical properties was evaluated [14].…”

Section: Resultsmentioning

confidence: 99%

Deprotonation/Protonation Induced Spectral Switching of 1,8-Naphthalimide Dye

Zhang

Zhao

et al. 2014

Molecular Crystals and Liquid Crystals

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In this contribution, a new sensitive colorimetric chemosensors based naphthalimide was synthesized and characterized by NMR and mass spectroscopic techniques. Upon the addition of OH-, the solution of dye change its color from yellowish to deep blue, which can be easily observed by naked eye. The sensors show good selective against other common anions, including strong Lewis base F − . The effects of deprotonation/protonation imposed on absorption spectrum were investigated. Further quantum chemical calculation uncovered the underlying signal mechanism. The lowered energy gap between HOMO/LUMO in NB-H leads to the longest maximum absorption (665 nm).

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“…A number of studies demonstrate that the interplay between theory and experiment is capable of providing useful insights into the understanding of the the nature of molecules [10,11]. Among the various kinds of OLEDs materials, 1,8-naphthalimide (NI) derivatives usually exhibit strong fluorescence and good photostability [12][13][14]. They have been widely used as the most important materials for fabrication of OLEDs.…”

Section: Introductionmentioning

confidence: 99%

Rational Design of Star-Shaped Molecules with Benzene Core and Naphthalimides Derivatives End Groups as Organic Light-emitting Materials

2014

Organic Chem Curr Res

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Synthesis, structural analysis and application of a series of solid-state fluorochromes—aryl hydrazones of 4-hydrazino-N-hexyl-1,8-naphthalimide

Cited by 7 publications

References 40 publications

Experimental and theoretical study on the absorption and fluorescence properties of substituted aryl hydrazones of 1,8-naphthalimide

Experimental and theoretical study on the absorption and fluorescence properties of substituted aryl hydrazones of 1,8-naphthalimide

Deprotonation/Protonation Induced Spectral Switching of 1,8-Naphthalimide Dye

Rational Design of Star-Shaped Molecules with Benzene Core and Naphthalimides Derivatives End Groups as Organic Light-emitting Materials

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