Synthesis and absorption properties of new yellow-green emitting benzo[de]isoquinoline-1,3-diones containing hindered amine and 2-hydroxyphenylbenzotriazole fragments

Bojinov, Vladimir B.; Panova, Ionka P.

doi:10.1016/j.dyepig.2006.03.016

Cited by 33 publications

(10 citation statements)

References 56 publications

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“…Table II compares the E exc and f values thus obtained with their theoretical counterparts. The experimental f values were calculated from the following equation [58]:…”

Section: Theoretical and Experimental Study Of The Excitation Energiementioning

confidence: 99%

Impact of the ionic forms on the UV–Vis spectra 2‐hydroxybenzylamine. A TD‐DFT study

Adrover¹,

Frau²,

Caldés³

et al. 2010

Int J of Quantum Chemistry

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PCM-TD-DFT computations were used to examine the electronic transitions exhibited by the molecular species of 2-hydroxybenzylamine (2-BNZ). The theoretical results thus obtained were found to accurately fit their experimental counterparts and to afford the assignation of the different experimental electronic transitions to 2-BNZ tautomers present in the solution. Also, the HCTH functional was found to accurately reproduce electronic excitations in the cationic species and neutral tautomer, and the B3LYP functional to provide accurate predictions of the transitions for the anionic species and zwitterionic tautomer.

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“…Table II compares the E exc and f values thus obtained with their theoretical counterparts. The experimental f values were calculated from the following equation [58]:…”

Section: Theoretical and Experimental Study Of The Excitation Energiementioning

confidence: 99%

Impact of the ionic forms on the UV–Vis spectra 2‐hydroxybenzylamine. A TD‐DFT study

Adrover¹,

Frau²,

Caldés³

et al. 2010

Int J of Quantum Chemistry

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“…1,8-Naphthalimides 1 and 2 were synthesized by consecutive reactions of 4-nitro-1,8-naphthalic anhydride first with 2-(5-amino-2H-benzotriazol-2-yl)phenol (compound 1) or 2-amino-6-(2H-benzotriazol-2-yl)-4-methylphenol (compound 2) in glacial acetic acid at 110 C and then with 2,2,6,6-tetramethylpiperidin-4-ylamine in DMF at room temperature as described before [19]. All solvents (Fluka, Merck) were of p.a.…”

Section: Methodsmentioning

confidence: 99%

“…The absorption maximum of 2-(5-amino-2H-benzotriazol-2-yl)phenol (l A1 ¼ 360 nm, precursor for dye 1) was 36 nm bathochromically shifted than that of 2-amino-6-(2H-benzotriazol-2-yl)-4-methylphenol (l A1 ¼ 324 nm, precursor for dye 2), which could be related to the difference in the intramolecular hydrogen bond strength due to the position effect of the electron-donating amino group in the benzotriazole moiety [19]. After acylation with 1,8-naphthalic anhydride the electron-donating activity of the amino group decreases strongly and the benzotriazole absorption of dye 1 was shifted hypsochromically, while that of dye 2 -bathochromically.…”

Section: Tablementioning

confidence: 97%

“…The quantum yields of fluorescence were calculated relative to Coumarin 6 (V ref ¼ 0.78) as a reference compound [20]. As seen from Table 1, the quantum yields of fluorescence of dyes 1 and 2 in DMF are vastly lower in respect to those in chloroform solution [19] and are lower in comparison with the data for other 1,8-naphthalimides [16c,24a]. This phenomenon might be caused by the possible photoinduced electron transfer (PET) from the piperidine nitrogen donor (receptor) to the 4-amino-1,8-naphthalimide fluorophore through the piperidinyl ring.…”

Section: Tablementioning

confidence: 99%

“…Owing to the basicity of the amine group, these serve as fluorescent sensors which are finding use in physiology research [18]. Recently, we have synthesized new yellow-green emitting 1,8-naphthalimides, containing differing in their action hindered amine and 2-hydroxyphenylbenzotriazole fragments, designed as highly photostabile additives for ''one-step'' fluorescent dyeing and photostabilization of polymers [19]. Therefore, it was of interest to see if 2,2,6,6-tetramethylpiperidine analogues of the 4-aminoalkyl-1,8-naphthalimide fluorophores would shed further light on this issue.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Novel 4-(2,2,6,6-tetramethylpiperidin-4-ylamino)-1,8-naphthalimide based yellow-green emitting fluorescence sensors for transition metal ions and protons

Bojinov

Panova

2009

Dyes and Pigments

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Theoretical investigation into optical and electronic properties of 1,8-naphthalimide derivatives

Jin

Tang

2013

J Mol Model

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A series of 1,8-naphthalimide derivatives has been designed to explore their optical, electronic, and charge transport properties as charge transport and/or luminescent materials for organic light-emitting diodes (OLEDs). The frontier molecular orbitals (FMOs) analysis have shown that the vertical electronic transitions of absorption and emission are characterized as intramolecular charge transfer (ICT) for electron-donating and aromatic groups substituted derivatives. However, the ICT character of the electron-withdrawing substituted derivatives is not significant. The calculated results show that their optical and electronic properties are affected by the substituent groups in 4-position of 1,8-naphthalimide. Our results suggest that 1,8-naphthalimide derivatives with electron-donating -OCH3 and -N(CH3)2 (1 and 2), electron-withdrawing -CN and-COCH3 (3 and 4), 2-(thiophen-2-yl)thiophene (5), 2,3-dihydrothieno[3,4-b][1, 4]dioxine (6), 2-phenyl-1,3,4-oxadiazole (7), and benzo[c][1,2,5]thiadiazole (8) fragments are expected to be promising candidates for luminescent materials for OLEDs, particularly for 5 and 7. In addition, 3 and 7 can be used as promising hole transport materials for OLEDs. This study should be helpful in further theoretical investigations on such kind of systems and also to the experimental study for charge transport and/or luminescent materials for OLEDs.

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Synthesis and absorption properties of new yellow-green emitting benzo[de]isoquinoline-1,3-diones containing hindered amine and 2-hydroxyphenylbenzotriazole fragments

Cited by 33 publications

References 56 publications

Impact of the ionic forms on the UV–Vis spectra 2‐hydroxybenzylamine. A TD‐DFT study

Impact of the ionic forms on the UV–Vis spectra 2‐hydroxybenzylamine. A TD‐DFT study

Novel 4-(2,2,6,6-tetramethylpiperidin-4-ylamino)-1,8-naphthalimide based yellow-green emitting fluorescence sensors for transition metal ions and protons

Theoretical investigation into optical and electronic properties of 1,8-naphthalimide derivatives

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