Amino derivatives of 1,8-naphthalic anhydride and derived dyes for synthetic-polymer fibres

Peters, A. T.; Bide, Martin

doi:10.1016/0143-7208(85)85005-1

Cited by 92 publications

(23 citation statements)

References 12 publications

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“…The energy gaps of 1,8-naphthalimides could also be tuned by chemical modification of their structures, especially by substitution at the 4-position. They have low reduction potentials (about −1.1 V versus SCE) [38] and high photostability [18], making them good candidates for use as n-type materials in OLEDs. None of the naphthalimide compounds have a detectable oxidation wave in acetonitrile and dichloromethane, putting it outside of the window available in these solvents (up to 2.0 V) [27].…”

Section: Resultsmentioning

confidence: 99%

“…1,8-Naphthalimide derivatives have photophysical properties, which have been widely used as brilliant yellow dyes in synthetic fiber technology and as optical brightener [18,19], as functional segment for the design of dual-mode chemical (protons)/electrochromic molecular switches [20], and as functional fluorescent imaging polymer. [21,22] Naphthalimide derivatives are also an attractive class of electron-deficient organic materials for OLEDs and are used as a new type of electron-transporting emitting materials for both small molecule and polymer-based OLEDs with high performance, good light stability, high fluorescent quantum yield, and high electron affinity [23,24].…”

Section: Introductionmentioning

confidence: 99%

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1,8-Naphthalimides for non-doping OLEDs: the tunable emission color from blue, green to red

Gan

Song

Hou

et al. 2004

Journal of Photochemistry and Photobiology A: Chemistry

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Substitution at the 4-position of 1,8-naphthalimide with electron-donating groups can increase fluorescent quantum yields and change emissive wavelengths from blue to red. Based on this molecular design concept, novel naphthalimide derivatives containing Schiff base moiety were prepared by condensing 4-hydrazino-1,8-naphthalimides with the aldehydes. Amino conjugation between the 4-amino-1,8-naphthalimide and the substituted moiety resulted in red shift of the absorption and fluorescence maximum wavelengths in the acetonitrile solution and in the net solid film. In the meantime, concentration-quenching effect of fluorescence for common luminescent materials was avoided. Some of these dyes emit brilliant red fluorescence in solid films and were used as non-doping emissive materials to fabricate electroluminescence devices. Based on these results, guidelines for the molecular design of non-doping red emissive materials for OLED applications are presented in this paper.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

1,8-Naphthalimides for non-doping OLEDs: the tunable emission color from blue, green to red

Gan

Song

Hou

et al. 2004

Journal of Photochemistry and Photobiology A: Chemistry

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“…These compounds can be employed as dyes for natural and synthetic fibers [1], optical brighteners in detergents, textiles, polymeric materials [1–3] and chemiluminiscent agents [4]. Owing to the high fluorescence quantum yields 1,8-naphthalimides are used as laser dyes [5–6].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and spectroscopic properties of 4-amino-1,8-naphthalimide derivatives involving the carboxylic group: a new molecular probe for ZnO nanoparticles with unusual fluorescence features

Bekere¹,

Gachet²,

Lokshin³

et al. 2013

Beilstein J. Org. Chem.

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SummaryOf a series of 4-substituted 1,8-naphthalimides, fluorescent 4-(6-piperidinyl-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)benzoic acid (4) was found to be a sensitive molecular probe for ZnO nanoparticles. We investigated in detail one- and two-photon absorption properties of this fluorophore. In nonpolar solvents, the acid 4 absorbs at about 400 nm and fluoresces at 500 nm with a fluorescence lifetime of about 7 ns, similar to the ester 6 and typical of the lifetimes of other derivatives of this type. Although the anionic form of this acid is not fluorescent, partial ionization of 4 in polar solvents, such as ethanol and acetonitrile, is not only accompanied by the expected decrease in the fluorescence quantum yield, but also gives rise to bathochromic shifts of both absorption and fluorescence and dual fluorescence with lifetimes of 0.2–0.3 ns and 6 ns ascribed to the formation of anionic complexes. The interaction with the ZnO surface brings about further considerable changes in the fluorescence patterns.

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“…Fluorescent naphthalimide dyes have bright colour and a very good dyeing effect conditioned by fluorescence, making them preferable for dyeing synthetic polymers and textile materials [1][2][3] . The introduction of an unsaturated, polymerizable double bond into naphthalimide dyes allows the combination of the two processes, viz.…”

Section: Introductionmentioning

confidence: 99%

Fluorescent polyacrylonitrile with 1,8-naphthalimide side chains

Grabchev¹,

Philipova

1999

Angew. Makromol. Chem.

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Amino derivatives of 1,8-naphthalic anhydride and derived dyes for synthetic-polymer fibres

Cited by 92 publications

References 12 publications

1,8-Naphthalimides for non-doping OLEDs: the tunable emission color from blue, green to red

1,8-Naphthalimides for non-doping OLEDs: the tunable emission color from blue, green to red

Synthesis and spectroscopic properties of 4-amino-1,8-naphthalimide derivatives involving the carboxylic group: a new molecular probe for ZnO nanoparticles with unusual fluorescence features

Fluorescent polyacrylonitrile with 1,8-naphthalimide side chains

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