N-substituted 1,8-naphthalimide derivatives as high efficiency laser dyes

Pardo, A.; Martín, E.; Poyato, J.M.L.; Camacho, J.J.; Guerra, José Antonio Iglesias; Weigand, Rudolf; Braña, Miguel F.; Castellano, José María

doi:10.1016/1010-6030(89)87007-8

Cited by 37 publications

(17 citation statements)

References 10 publications

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“…1,8-Naphthalimide and bisnaphthalimide derivatives are promising anticancer agents [9,10], the sulfonated derivatives are good antiviral agents with selective in vitro activity against the human immunity deficiency virus, HIV-1 [11]. Due to their photo-physical and photo-chemical properties the 1,8-naphthalimide derivatives can be used as fluorescence dyes for solar energy collectors and photosynthesis under concentrated sunlight [12], fluorescent markers in biological cells [13] as well as laser active media [14][15][16]. Recently, naphthalimides have also found applications in organic thin film field-effect transistors (OFETs), integrated circuit, displays, memory cards, chemical and pressure sensors, smart price tags and labels [17].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Photophysical Characterizations of Thermal -Stable Naphthalene Benzimidazoles

2011

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Section: Introductionmentioning

confidence: 99%

Synthesis and Photophysical Characterizations of Thermal -Stable Naphthalene Benzimidazoles

2011

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“…This group also studied the effect of pH of the medium on the fluorescence properties of aminonaphthalimides and explored possible use of these systems in fluorescence sensing of the transition-metal ions such as Cu 2+ − and ourselves. − …”

Section: Introductionmentioning

confidence: 99%

Influence of the Structure of the Amino Group and Polarity of the Medium on the Photophysical Behavior of 4-Amino-1,8-naphthalimide Derivatives

2002

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Photophysical behavior of two series of 4-amino-1,8-naphthalimide derivatives differing in the amino functionality has been studied as a function of the polarity of the medium. The location of the lowest singlet state of the systems, intramolecular charge transfer (ICT) in nature, is largely controlled by the conformation of the 4-amino group rather than its electron-donating ability. The fluorescence properties of the systems are strongly dependent on the nature of the amino group as well as on the polarity of the media. An increase in the length of the dialkyl groups connected to the amino nitrogen or an increase in the size of the ring containing the amino nitrogen enhances the nonradiative deactivation of the fluorescent state of the molecule. The nonradiative relaxation process is facilitated by an increase in the polarity of the media. The present results suggest that the radiationless deactivation of the fluorescent state of the systems is dependent on the nitrogen inversion rate at the amino group.

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“…In addition to the biological interest, naphthalenic imides have been used for technological purposes, such as in optical brighteners and laser dyes . More recently, the potential applications of this class of compounds were further broadened with their use as building blocks in supramolecular assemblies and new molecular materials.…”

Section: Introductionmentioning

confidence: 99%

Solubilization of 1,4,5,8-Naphthalenediimides and 1,8-Naphthalimides through the Formation of Novel Host−Guest Complexes with α-Cyclodextrin

Brochsztain

Politi

1999

Langmuir

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Solubility studies were performed in aqueous solutions of 1,8-naphthalimides and 1,4,5,8-naphthalenediimides (Scheme 1). A large solubility increase was found for N-butyl-1,8-naphthalimide (MBN) and N, 4,5, in the presence of R-cyclodextrin (R-CD), indicating the formation of inclusion complexes. The presence of the N-butyl group is required for complex formation, leading to the conclusion that the butyl groups are the binding sites for R-CD. Accordingly, the analysis of solubility isotherms for the systems MBN/R-CD and DBN/R-CD showed the presence of 1:1 complexes for the former and of both 1:1 and 1:2 complexes for the latter. Association constants for the two systems were estimated, giving K ) 470 M -1 for the MBN/R-CD complex and K11 ) 1316 M -1 and K12 ) 329 M -1 for the stepwise association constants in the DBN/R-CD system. MBN undergoes hydrolysis in water, but the reaction is inhibited upon complexation with R-CD. The remarkable solubilization in water and stabilization toward hydrolysis makes these novel complexes of imides and diimides with R-CD potentially useful in the pharmaceutical applications known for these imides, as well as in the preparation of new materials, like polyimide-based polyrotaxanes.

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N-substituted 1,8-naphthalimide derivatives as high efficiency laser dyes

Cited by 37 publications

References 10 publications

Synthesis and Photophysical Characterizations of Thermal -Stable Naphthalene Benzimidazoles

Synthesis and Photophysical Characterizations of Thermal -Stable Naphthalene Benzimidazoles

Influence of the Structure of the Amino Group and Polarity of the Medium on the Photophysical Behavior of 4-Amino-1,8-naphthalimide Derivatives

Solubilization of 1,4,5,8-Naphthalenediimides and 1,8-Naphthalimides through the Formation of Novel Host−Guest Complexes with α-Cyclodextrin

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