Photophysical properties of 1,8-naphthalimide derivatives

Pardo, A.; Poyato, J.M.L.; Martín, E.

doi:10.1016/0047-2670(87)80023-0

Cited by 38 publications

(15 citation statements)

References 6 publications

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“…Compound (4), N-butyl4-cyano-1,8naphthalimide was formed from the 4-bromo analogue by heating with copper cyanide in hot quinoline solution. Compound (5) was obtained by the interaction of 4bromo-1,8-naphthalic anhydride with aniline in hot ethanol and treatment of the purified product with propylamine in hot N-methylpyrrolidinone. Compound (6) resulted from treatment of 4-nitro-1,8-naphthalimide with butylamine in hot dimethylformamide and from 4-bromo-1,8-naphthalimide with butylamine in hot N-methylpyrrolidinone.…”

Section: Methodsmentioning

confidence: 99%

The UV–visible absorption and fluorescence of some substituted 1,8-naphthalimides and naphthalic anhydrides

Alexiou¹,

Tychopoulos²,

Ghorbanian³

et al. 1990

J. Chem. Soc., Perkin Trans. 2

236

150

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Section: Methodsmentioning

confidence: 99%

The UV–visible absorption and fluorescence of some substituted 1,8-naphthalimides and naphthalic anhydrides

Alexiou¹,

Tychopoulos²,

Ghorbanian³

et al. 1990

J. Chem. Soc., Perkin Trans. 2

236

150

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“…The Stokes shift of 1 is small (3540 cm À1 ), its value is similar as for the parent 1,8-naphthalimide. 39 The excited state properties of N-propyl-1,8-naphthalimide are strongly modified by the piperidinyl substitution. As can be seen in Fig.…”

Section: Solvatochromism In Absorption and Fluorescence Spectramentioning

confidence: 99%

Experimental evidence of TICT state in 4-piperidinyl-1,8-naphthalimide – a kinetic and mechanistic study

Szakács

Rousseva

Bojtár

et al. 2018

Phys. Chem. Chem. Phys.

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The excited state processes in N-propyl-4-piperidinyl-1,8-naphthalimide have been studied by measuring its fluorescence spectra and decay curves in solvents of different polarity and viscosity and also in a frozen solvent glass. The results unanimously proved the formation of a dark twisted intramolecular charge transfer (TICT) state from the emissive charge transfer (CT) species, the direct product of excitation. The rate coefficients of the TICT process and the deactivations of the CT and TICT species were determined, using a reversible two-state kinetic model. The temperature dependence of the kinetic data was consistent with a kinetic barrier consisting of three terms, the inherent barrier of the reaction, and the contributions of the solute-solvent interactions related to the solvent viscosity and polarity. The potential energy surfaces were calculated in the S0 and the S1 states along the coordinate of turning motion which was conclusive concerning the direction of the twisting and indicated a possible conformational change of the piperidinyl unit. The theoretical calculations confirmed that the TICT species is dark and has a stronger charge transfer character compared to the CT state.

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“…Instead, Berces et al in their pivotal publications, concluded that both short wavelength emission (SW) and long wavelength emission (LW) excited states originated from a common Franck–Condon state whereupon subsequent relaxation and emission of the SW originated from an orthogonal structure and LW emission resulted from a coplanar structure. − These studies concluded that the photophysical mechanism for the dual-fluorescent NIs was neither ESPT nor TICT. Further spectroscopic investigations of 1,8-NIs demonstrated that two emitting states S 1 and S 2 were responsible for SW and LW fluorescence − …”

Section: Introductionmentioning

confidence: 99%

Electronic Properties and Electroluminescent OLED Performance of Panchromatic Emissive N-Aryl-2,3-naphthalimides

et al. 2017

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This report investigates the excited-state properties of a series of N-aryl-2,3-naphthalimides along with their fabrication into OLEDs and electroluminescence measurements. The N-aryl-2,3-NIs substituted specifically with chloro, fluoro, and methoxy substituents were chosen because of their unique propensity to display two emission bands or panchromatic fluorescence. Using the Lippert-Mataga analysis along with TD-DFT calculations, the excited states were determined to be n,π* and π,π*. The TD-DFT calculations on the geometries of the excited states indicate that the excited state shows a planar structure. The origin of both the short wavelength (SW) and long wavelength (LW) emission were correlated to specific geometries such that the SW emission originates from an "angled" structure in the excited state, and LW emission originates from an excited state of coplanar structure. All of the dyes investigated readily formed good films under ultrahigh vacuum deposition. The molecular energy levels of these compounds (HOMO and LUMO) were measured with cyclic voltammetry. Band gaps were also measured in both electrochemical and optical methods and indicate that the HOMOs of these fluorophores matched well with the anode (ITO work function), and their LUMOs matched well with the cathode (LiF/Al). To compare photoluminescence of the four dyes with their potential electroluminescence, three OLED devices were designed and fabricated. The electroluminescent spectra of these devices indicate that the panchromatic fluorescence, observed in solution, shifts toward the red in the solid-state. A plausible explanation appears to stem from an inability to inject electrons to the higher LUMO+1 orbitals; a process observed in the solution phase. Hence, the short wavelength fluorescence peak, a key component to panchromatic luminescence disappears in the OLED device. The observed EL spectrum from these smaller heteroatomic architectures is on par if not more broadly emissive than rubrene (5,6,11,12-tetraphenyltetracene), a red-colored CH polycyclic aromatic hydrocarbon, that displays an orange-color EL.

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Photophysical properties of 1,8-naphthalimide derivatives

Cited by 38 publications

References 6 publications

The UV–visible absorption and fluorescence of some substituted 1,8-naphthalimides and naphthalic anhydrides

The UV–visible absorption and fluorescence of some substituted 1,8-naphthalimides and naphthalic anhydrides

Experimental evidence of TICT state in 4-piperidinyl-1,8-naphthalimide – a kinetic and mechanistic study

Electronic Properties and Electroluminescent OLED Performance of Panchromatic Emissive N-Aryl-2,3-naphthalimides

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