Synthesis and bromination of 4-alkylamino- N -alkyl-1,8-naphthalimides

Chang, Shao-Chieh; Utecht, Ronald E.; Lewis, David E.

doi:10.1016/s0143-7208(99)00045-5

Cited by 39 publications

(7 citation statements)

References 23 publications

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“…N ‐(Prop‐1‐yne‐3‐yl)‐4‐(piperidine‐1‐yl)‐1,8‐naphthalimide has been prepared in a high isolated yield from commercially available 4‐nitro‐1,8‐naphthalic anhydride by the two‐step process (Scheme ) based on already known reactions 63–67. The high reproducibility of the overall process was observed.…”

Section: Resultsmentioning

confidence: 96%

Poly(disubstituted acetylene)s With Pendant Naphthalimide‐Based Fluorophore Groups

Sivkova

Vohlı́dal

Bláha

et al. 2012

Macro Chemistry & Physics

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New stable polyacetylenes whose quantum yield of fl uorescence is increased up to 62% because of the presence of pendant 4-(piperidine-1-yl)-1,8-naphtalimide groups are described. The polymers are prepared by two-step modifi cation of copolymers of 1-(4-tert -butylphenyl)-6-chlorohex-1-yne and 1-phenylhex-1-yne consisting of the exchange of chlorine atoms at side groups for azide groups and subsequent Huisgen click reaction of the azide groups with ethynyl groups of N -(prop-1-yne-3-yl)-4-(piperidine-1-yl)-1,8-naphthalimide. Modifi cation is evidenced by 1 H NMR, IR, Raman and UV-vis spectroscopy. Modifi ed polymers show the excitation energy transfer from their main chains on fl uorophores and nearly preservation of fl uorescence properties of fl uorophores upon their binding to polymer chains.

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Section: Resultsmentioning

confidence: 96%

Poly(disubstituted acetylene)s With Pendant Naphthalimide‐Based Fluorophore Groups

Sivkova

Vohlı́dal

Bláha

et al. 2012

Macro Chemistry & Physics

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“…The synthesis and structure of the new luminescent dye is described in Scheme . The highly luminescent material N ‐(prop‐1‐yne‐3‐yl)‐4‐(morpholine‐1‐yl)‐1,8‐naphthalimide ( NF ) was prepared using a simple sequence of robust reactions from an readily available 4‐nitro‐1,8‐naphthalic anhydride based on previously published methods . The presence of the functional alkyne group in the NF luminescent dye enabled the reaction with an azide containing a polythiophene‐based polymer ( PHT‐N 3 ) followed by a Cu(I)‐catalyzed Huisgen azide‐alkyne dipolar cycloaddition (click chemistry) and formation of a novel polymer, PHT‐NF (see Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Attachment of a 1,8‐Naphthalimide Moiety to a Conjugated Polythiophene Efficiently Improves the Sensing Abilities of Naphthalimide‐Based Materials

Hladysh

Murmiliuk

Vohlı́dal

et al. 2018

Macro Chemistry & Physics

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A novel polythiophene‐based conjugated polymer bearing 1,8‐naphthalimide‐based pendants is prepared by a two‐step modification of regioregular poly[3‐(6‐bromohexyl)thiophene] involving a nucleophilic substitution reaction of the bromide end‐groups with sodium azide followed by a robust, copper‐catalyzed Huisgen click reaction with a novel 1,8‐naphthalinmide derivative containing an active, N‐substituted propyne group. Both the polymer and the highly luminescent‐active synthesized dye are extensively studied in solution by UV–vis spectroscopy, photoluminescence, NMR, light‐scattering and isothermal titration calorimetry. The materials prepared are considered potential chemosensors for different transition metals, such as Fe2+, Co2+, Ni2+, Cu2+, Zn2+, and Cd2+. Luminescence quenching shows that these materials have a higher sensitivity to Fe2+ than to the other metal ions tested. Moreover, the 1,8‐naphthalimide‐based conjugated polymer is more efficiently quenched by Fe2+ metal ions, at a significantly lower concentration and with a higher binding constant than its parent 1,8‐naphthalimide derivative, thus indicating a high potential for sensor development.

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“…Due to their strong fluorescence and high photostability, derivatives of 1,8-naphthalimide are widely used as fluorescent markers in biology, [10] light-emitting diodes, [11][12][13] photoinduced electron transfer sensors, [14][15][16][17][18] fluorescent switches, [19][20][21] and photochemotherapeutic inhibitors. [22][23][24][25][26] A number of 1,8-naphthalimide derivatives were screened for fluorescence and 7H-benz [de]benzimidazo [2,1-a]isoquinoline-7-one (BBIQ) selected for use as the fluorophore due to its strong fluorescence (as assessed by relative fluorescence quantum yields). [7, [27]-43] Since their development in the mid-1980s, PAMAM dendrimers have shown great potential in being utilised as drug delivery vehicles due to their biocompatibility, low polydispersity indices and high hydrophilicity.…”

Section: Introductionmentioning

confidence: 99%

Auto-fluorescent PAMAM-based dendritic molecules and their potential application in pharmaceutical sciences

El-Betany

Kamoun

James

et al. 2020

International Journal of Pharmaceutics

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The epithelial permeation of water-soluble fluorescent PAMAM dendrons based on 7Hbenz[de] benzimidazo [2,1-a] isoquinoline-7-one as a fluorescent core across epithelial cell models MDCK I and MDCK II has been quantified.Hydrodynamic radii have been derived from self-diffusion coefficients obtained via pulsedgradient spin-echo Nuclear Magnetic Resonance (PGSE-NMR). Results indicate that these dendritic molecules are molecularly disperse, non-aggregating, and only slightly larger than their parent homologues. MDCK I permeability studies across epithelial barriers show that these dendritic molecules are biocompatible with the chosen epithelial in-vitro model and can permeate across MDCK cell monolayers. Permeability is demonstrated to be a property of dendritic size and cell barrier restrictiveness indicating that paracellular mechanisms play the predominant role in the transport of these molecules.

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Synthesis and bromination of 4-alkylamino- N -alkyl-1,8-naphthalimides

Cited by 39 publications

References 23 publications

Poly(disubstituted acetylene)s With Pendant Naphthalimide‐Based Fluorophore Groups

Poly(disubstituted acetylene)s With Pendant Naphthalimide‐Based Fluorophore Groups

Attachment of a 1,8‐Naphthalimide Moiety to a Conjugated Polythiophene Efficiently Improves the Sensing Abilities of Naphthalimide‐Based Materials

Auto-fluorescent PAMAM-based dendritic molecules and their potential application in pharmaceutical sciences

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