Calculated and experimental spectra of some 1,8-naphthalimide derivatives

Karamancheva, Ilyana; Tadjer, Alia; Philipova, T.; Madjarova, Galia; Ivanova, Christina; Grozeva, T.

doi:10.1016/s0143-7208(97)00025-9

Cited by 14 publications

(8 citation statements)

References 12 publications

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“…1,8-Naphthalimides have been widely investigated because of their photophysical properties. [1][2][3][4][5][6][7][8] Naphthalimides are one of the most important building blocks for synthesis of efficient fluorescent materials showing large quantum yields and sizable Stokes shifts. Gan and coworkers synthesized some aryl hydrazones of 4-hydrazino-N-butyl-1,8-naphthalimide and studied their electronic and fluorescence spectra for application as materials for light emitting diodes (OLEDs).…”

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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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%

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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“…To prove that the obtained doublets of s and as (in KBr) are due to ED-EA interaction, we investigated the behavior of 1,8-naphtalimides in solvents with growing polarity: PhCH 3 , CHCl 3 , CH 3 CN, and DMSO. 9,10 It is established that in polar solvents the ED-EA interaction becomes stronger, which leads to splitting of the bands. Upon going from CHCl 3 to more polar solvents, such as CH 3 CN and DMSO, the intensity of the absorption band of CAO as increases, while that of CAO s decreases, and in DMSO, the band practically disappears.…”

Section: Structural Analysismentioning

confidence: 99%

Synthesis, spectral properties, and application of 1,8‐naphthalimide fluorophores for modified polymers

Philipova

Петков

2001

J of Applied Polymer Sci

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ABSTRACT:The presence of the epoxy group in the structure of 1,8-naphthalimide fluorophores opens up possibilities to prepare compounds with new valued properties through covalent bonding to both polyamide and epoxy oligomers. Two new 4-(1-amino-2,3-epoxypropyl)-9-substituted-1,8-naphthalimides were synthesized, and their absorption and fluorescence characteristics were determined. The introduction of the substituent contributes to both the yellow color and strong fluorescence of the compounds, the quantum yield being about 0.9. The possibility for structural coloration of polyamide textile materials and epoxy oligomers has been investigated. The modified polymers are with intense green fluorescence, possessing a strong resistance to various physicochemical treatments and light.

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“…In the case of naphthalimides, variations in the colours may be obtained by changes in the donor group in position 4 of the naphthalene moiety [4,8,9]. In our research, we have determined that the coupling between the 4-nitro-N-methyl-1,8-naphthalimide and 2-hydroxi-p-xylen produces an organic material 4-(o-oxi-p-xylen)-N-methyl-1,8-naphthalimide, which has the capacity to form films capable of blue light emissions.…”

Section: Introductionmentioning

confidence: 99%

Naphthalimide-derivative with blue electroluminescence for OLED applications

Triboni

Fernandes

Garcia

et al. 2015

Journal of Taibah University for Science

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The synthesis and characterization of the 4-(2-fenoxi-p-xileno)-N-methyl-1,8-naphthalimide, referred to here as NPOX, is described in this work. The characterization of NPOX was performed using proton nuclear magnetic resonance spectroscopy ( 1 H NMR), UV-visible and fluorescence emission spectroscopy. The LUMO and HOMO levels of NPOX were estimated using the electrochemical method, respectively, at 3.4 eV and 6.1 eV with an energy gap of 2.7 eV. The NPOX is soluble in chloroform such that when it evaporates, it becomes a transparent film with fluorescence emissions occurring at 456 nm when excited at 363 nm. Using the Space-Charge-Limited-Current (SCLC) model, we obtained the value of the mobility of the positive charge carriers to be μ ∼ = 5 × 10 −5 cm 2 V −1 s −1 . These properties raise the possibility of using the NPOX as the emitting layer in an organic light-emitting diode (OLED) with emission in the blue region, as demonstrated by the fabrication of an OLED with an ITO/PEDOT:PSS/NPOX/Al structure and light emission peaking at approximately 465 nm.

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Calculated and experimental spectra of some 1,8-naphthalimide derivatives

Cited by 14 publications

References 12 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

Synthesis, spectral properties, and application of 1,8‐naphthalimide fluorophores for modified polymers

Naphthalimide-derivative with blue electroluminescence for OLED applications

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