- Aggregation-induced emission or aggregation-caused quenching? Impact of covalent bridge between tetraphenylethene and naphthalimide
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Understanding the physical mechanisms governing aggregation-induced-emission (AIE) and aggregation-caused-quenching plays a vital role in developing functional AIE materials. In this work, tetraphenylethene (TPE, a classical AIEgen) and naphthalimide (NI, a popular fluorophore with ACQ characteristics) were connected through non-conjugated linkages and conjugated linkages. We showed that the nonconjugated-linkage of TPE to NI fragments leads to substantial PET in molecular aggregates and ACQ. In contrast, the conjugated connection between TPE and NI moieties results in the AIE phenomenon by suppressing twisted intramolecular charge transfer. This work provides an important guideline for the rational design of AIE materials.
- Ma, Xiaoxie,Chi, Weijie,Han, Xie,Wang, Chao,Liu, Shenghua,Liu, Xiaogang,Yin, Jun
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p. 1790 - 1794
(2021/03/08)
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- Peroxynitrite (ONOO-) generation from the HA-TPP@NORM nanoparticles based on synergistic interactions between nitric oxide and photodynamic therapies for elevating anticancer efficiency
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Due to biological safety and negligible toxicity, nitric oxide (NO) therapy has gained increasing interest in the field of cancer therapy during the past few years. However, individual NO cancer therapy normally exhibited limited therapeutic efficiency. In order to acquire satisfactory therapeutic outcomes, the NO therapy is usually combined with other therapeutic treatments, mostly chemotherapy. Herein, we constructed HA-TPP@NORM nanoparticles based on the co-assembly of an NO donor (NORM) and tetraphenylporphyrin (TPP)-modified hyaluronic acid, which can efficiently generate a highly biocidal molecule of peroxynitrite (ONOO-) via the synergistic interactions of the nitric oxide (NO) therapy and photodynamic therapy (PDT) to enhance the cancer therapeutic efficiency. In addition, MTT results exhibited that without light irradiation, the HA-TPP@NORM nanoparticles have favourable biocompatibility with the cell viability above 95% at the maximum TPP concentration (20 μg mL-1). Under simultaneous irradiation with 365 nm and 650 nm light, ONOO- can be efficiently produced in cancer cells via the direct coupling reaction of the generated NO and superoxide anion radical (O2-), which significantly enhanced the anticancer effect, when compared with individual NO therapy or PDT therapy. Therefore, the HA-TPP@NORM nanoparticles may provide a new insight into the design of efficiently NO-related cancer therapeutic systems.
- Jiang, Dawei,Yue, Tao,Wang, Guichen,Wang, Chaochao,Cao, Hongliang,Gao, Yun,Chen, Chao
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p. 162 - 170
(2019/12/26)
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- Efficient Intersystem Crossing in the Tr?ger's Base Derived From 4-Amino-1,8-naphthalimide and Application as a Potent Photodynamic Therapy Reagent
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Intersystem crossing (ISC) was observed for naphthalimide (NI)-derived Tr?ger's base, and the ISC was confirmed to occur by a spin-orbital charge-transfer (SOCT) mechanism. Conventional electron donor/acceptor dyads showing SOCT-ISC have semirigid linkers. In contrast, the linker between the two chromophores in Tr?ger's base is rigid and torsion is completely inhibited, which is beneficial for efficient SOCT-ISC. Femtosecond transient absorption (TA) spectra demonstrated charge-separation and charge-recombination-induced ISC processes. Nanosecond TA spectroscopy confirmed the ISC, and the triplet state is long-lived (46 μs, room temperature). The ISC quantum yield is dependent on solvent polarity (8–41 %). The triplet state was studied by pulsed-laser-excited time-resolved EPR spectroscopy, and both the NI-localized triplet state and triplet charge-transfer state were observed, which is in good agreement with the spin-density analysis. The Tr?ger's base was confirmed to be a potent photodynamic therapy reagent with HeLa cells (EC50=5.0 nm).
- Barbon, Antonio,Chen, Kepeng,Hou, Yuqi,Li, Shujing,Wang, Zhijia,Wu, Huijian,Yaglioglu, Halime Gul,Yildiz, Elif Akhuseyin,Zhang, Xue,Zhao, Jianzhang,Zhao, Yingjie
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- Expanding the Breadth of 4-Amino-1,8-naphthalimide Photophysical Properties through Substitution of the Naphthalimide Core
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Fluorescent sensors that illuminate specific molecules and chemical events allow the selective and sensitive study of the cellular environment. At the centre of this technology lies the fluorescent reporter molecule, and it is therefore crucial to provide a breadth of fluorophores with varying photophysical and biological behaviour. 4-Amino-1,8-naphthalimides are commonly employed in fluorescent sensors, but the narrow range of structural derivatives limits versatility of application. Here we report the synthesis and investigation of a set of twelve 4-amino-1,8-naphthalimides bearing an additional substituent on the aromatic core. Photophysical characterisation and time-dependent density functional theory studies provided insights into the structure–photophysical property relationships of these derivatives, which show an expanded range of emission wavelengths and other photophysical properties. These compounds could all be visualised within cells by confocal microscopy, showing cytoplasmic or lipid droplet localisation. Our studies have demonstrated that simple structural modification of 4-amino-1,8-naphthalimides provides derivatives with considerable breadth of behaviour that lend valuable versatility to the design of fluorescent sensors.
- Leslie, Kathryn G.,Jacquemin, Denis,New, Elizabeth J.,Jolliffe, Katrina A.
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supporting information
p. 5569 - 5573
(2018/03/21)
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- Nitric oxide donors, preparation and applications of nitric oxide donors
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The invention relates to nitric oxide donors, preparation and applications of the nitric oxide donors. In particular, the invention provides compounds which have structures represented by a formula I, wherein R2 is H, a C3-C8 naphthenic group or C1-C6 alkyl which is substituted by 1-2 materials optionally selected from C1-C4 alkoxy, -S(O)2-OH, and a substituent group of hydroxyl, and N is connected with a benzene ring of a fluorophore molecule. The invention also provides preparation methods for the compounds represented by the formula I, compositions containing the compounds represented in the formula I, and the applications of the compounds which are used as the nitric oxide donors.
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- Photophysics, Electrochemistry, Morphology, and Bioimaging Applications of New 1,8-Naphthalimide Derivatives Containing Different Chromophores
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A series of 1,8-naphthalimide-based fluorophores containing different chromophores with varying conjugation and electron richness at the imidic nitrogen atom are synthesized and characterized. These amine-functionalized naphthalimides are bipolar in nature and exhibit interesting optical and morphological variations attributable to the nature of the N substituents. Despite the fact that the dyes are structurally different owing to variation of the substituent on the imidic nitrogen atom, their electronic characteristics are similar and originate from the 4-aminonaphthalimide segment. Nevertheless, they exhibit variations in morphology in the microscopic domain, and this is attributable to structural differences. Further, these fluorescent dyes display biocompatibility and are used in the bioimaging of cells.
- Saini, Ankita,Thomas, K. R. Justin,Sachdev, Abhay,Gopinath, Packirisamy
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p. 2612 - 2622
(2017/10/07)
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- Photocalibrated NO Release from N-Nitrosated Napthalimides upon One-Photon or Two-Photon Irradiation
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NO donors are routinely used as the exogenous source in in vitro studies. However, the kinetics or the dose of NO release from the existing donors is not readily monitored. This complicates the elucidation of the involvement of NO in a biological response. We report herein a series of NO donors (NOD545a-g), whose NO release is triggered by UV light at 365 nm or a two-photon laser at 740 nm, and importantly, their NO release is accompanied by a drastic fluorescence turn-on, which has been harnessed to follow the kinetics and dose of NO release in a real-time fashion with spectroscopic methods or microscopic methods in in vitro studies. These merits have rendered NOD545a-g useful molecular tools in NO biology.
- Zhang, Ziqian,Wu, Jiayao,Shang, Zhihao,Wang, Chao,Cheng, Jiagao,Qian, Xuhong,Xiao, Yi,Xu, Zhiping,Yang, Youjun
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p. 7274 - 7280
(2016/07/27)
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- A ratiometric fluorescent probe for the detection of hydroxyl radicals in living cells
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A naphthalimide-naphthyridine derivative has been synthesized for the detection of hydroxyl radicals. It can distinguish hydroxyl radicals from other reactive oxygen species with high selectivity and short response time. Moreover, it has no cellular toxicity, and can be effectively used for intracellular detection of hydroxyl radicals. The Royal Society of Chemistry 2014.
- Meng, Luyan,Wu, Yongquan,Yi, Tao
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supporting information
p. 4843 - 4845
(2014/05/06)
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- Energy transfer in aminonaphthalimide-boron-dipyrromethene (BODIPY) dyads upon one-and two-photon excitation: Applications for cellular imaging
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Aminonaphthalimide-BODIPY energy transfer cassettes were found to show very fast (kEET≈1010-1011 s-1) and efficient BODIPY fluorescence sensitization. This was observed upon one-and two-photon excitation, which extends the application range of the investigated bichromophoric dyads in terms of accessible excitation wavelengths. In comparison with the direct excitation of the BODIPY chromophore, the two-photon absorption cross-section δ of the dyads is significantly incremented by the presence of the aminonaphthalimide donor [δ≈10 GM for the BODIPY versus 19-26 GM in the dyad at λexc=840 nm; 1 GM (Goeppert-Mayer unit)=10-50 cm4 s molecule-1 photon-1]. The electronic decoupling of the donor and acceptor, which is a precondition for the energy transfer cassette concept, was demonstrated by time-dependent density functional theory calculations. The applicability of the new probes in the one-and two-photon excitation mode was demonstrated in a proof-of-principle approach in the fluorescence imaging of HeLa cells. To the best of our knowledge, this is the first demonstration of the merging of multiphoton excitation with the energy transfer cassette concept for a BODIPY-containing dyad. Take two: Aminonaphthalimide-BODIPY energy transfer cassettes were designed in order to take advantage for bioimaging from one-and two-photon excitation coupled with energy transfer. The bichromophoric dyads showed ultrafast and highly efficient energy transfer and were used for confocal fluorescence microscopy imaging of HeLa cells as bio-relevant models. Copyright
- Collado, Daniel,Remon, Patricia,Vida, Yolanda,Najera, Francisco,Sen, Pratik,Pischel, Uwe,Perez-Inestrosa, Ezequiel
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supporting information
p. 797 - 804
(2014/03/21)
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- A facile route to functionalized naphthalimide dyes via copper-catalyzed C-N, C-O, and C-S cross-coupling reactions in aqueous medium
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A mild, facile, and efficient synthesis of fluorescent naphthalimide dyes via CuI-catalyzed CN, CO, and CS Ullman-type condensation reactions using amines, alcohols, and thiols is described. The reactions were carried out in the presence of KF/Al2O3 as a mild basic support in water as a green solvent. This protocol tolerates a wide range of functional groups and provides functionalized naphthalimide dyes in good to excellent yields.
- Bardajee, Ghasem Rezanejade
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p. 4937 - 4941
(2013/08/28)
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- A 4-aminonaphthalimide based environmentally sensitive fluorescence probe
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A simply synthesized 4-aminonaphthalimide derivative 1 expresses both polarity and viscosity sensitive fluorescence spectra, indicating its potential usage as an environmentally sensitive fluorescence probe. By comparing the fluorescence behavior of 1 with that of a known 4-aminonaphthalimide derivative 2, it was found that the substitution of the 4-amino group has profound influence on the environmentally sensitive fluorescence properties of 4-aminonaphthalimide.
- Wu, Zhi-Yong,Cui, Jing-Nan,Qian, Xu-Hong,Liu, Tian-Yu
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p. 359 - 361
(2013/07/04)
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- Synthesis of thionaphthalimides and their dual Hg2+-selective signaling by desulfurization of thioimides
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A series of new thionaphthalimide derivatives were prepared, and their Hg2+-selective signaling behavior was investigated in aqueous acetonitrile solution. A monothionaphthalimide (anti) exhibited pronounced Hg2+-selective chromogenic signaling behavior through a solution color change from red to yellow, which was easily detectable by eye. It (anti) also showed prominent off-on type Hg2+-selective fluorescent signaling behavior. The signaling is due to the Hg2+-assisted desulfurization of the thioimide to its imide structure. The presence of other common metal ions did not interfere with the Hg2+-signaling of the monothionaphthalimide (anti). The detection limit of monothionaphthalimide (anti) for the determination of Hg2+ ions in 30% aqueous acetonitrile was estimated to be 2.7 μM.
- Moon, Jung Ok,Choi, Myung Gil,Sun, Taihao,Choe, Jong-In,Chang, Suk-Kyu
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p. 170 - 175,6
(2020/08/20)
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- Water-solvent method for the synthesis of N-substituted and N-,4-disubstituted 1,8-naphthalimides under microwave irradiation
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A preparation of a series of N-and N-,4-substituted 1,8-naphthalimides using water as solvent under microwave irradiation, which proceeded via efficient and green reaction of 1,8-naphthalic anhydride derivatives with different amines, is described.
- Zhang, Ye,Feng, Shao-Bo,Wang, Kai,Yi, Xiang-Hui,Wang, Heng-Shan,Pan, Ying-Ming
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experimental part
p. 3042 - 3052
(2012/08/14)
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- Microwave-assisted synthesis and evaluation of naphthalimides derivatives as free radical scavengers
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A facile and efficient microwave-assisted reaction of 1,8-naphthalic anhydride derivatives with primary amines, leading to the synthesis of 1,8-naphthalimides, has been developed. Subsequently, the free radical scavenging properties of the 1,8-naphthalimide derivatives were evaluated against 2,2-diphenyl-1-picrylhydrazyl (DPPH). The results showed that the scavenging activities of compounds 2a, NBNA, 3b, and 3c were more efficient than that of the common synthetic antioxidant 2,6-diterbutyl- 4-methylphenol (BHT), with IC50 values of 61.9, 54.0, 42.2, and 43.1 μM, respectively. The imide groups introduced at position 4 as well as the nitro functionality at position 3 of the naphthalene moiety were the major contributors to the free radical scavenging activities. Springer Science+Business Media, LLC 2010.
- Zhang, Ye,Feng, Shaobo,Wu, Qiang,Wang, Kai,Yi, Xianghui,Wang, Hengshan,Pan, Yingming
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experimental part
p. 752 - 759
(2012/05/20)
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- NAPHTHALIMIDE DERIVATIVES AS ANTIVIRAL AGENTS
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The present invention relates to the use of naphthalimide compounds of formula (I), wherein A, B, R1, R2, n and Ra are defined herein, and pharmaceutically acceptable salts thereof, for the treatment or prevention of infection by hepatitis C virus.
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Page/Page column 37
(2010/10/20)
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- Efficient sonochemical synthesis of 3- and 4-electron withdrawing ring substituted N-alkyl-1,8-naphthalimides from the related anhydrides
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1,8-N-alkyl-naphthalimides substituted with electron withdrawing groups were readily prepared in high yields using ultrasound in aqueous media.
- Rezende Triboni, Eduardo,Berci Filho, Pedro,Gomes De Souza Berlinck, Roberto,Politi, Mario Jose
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p. 1989 - 1999
(2007/10/03)
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- Simple naphthalimide based anion sensors: Deprotonation induced colour changes and CO2 fixation
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The 4-amino-1,8-naphthalimide based chemosensors 2, 4 and 6 show striking green-to-purple colour changes due to the deprotonation of the 4-amino moiety on interaction with strongly basic anions such as F-: these colour changes reverse gradually
- Gunnlaugsson, Thorfinnur,Kruger, Paul E.,Jensen, Paul,Pfeffer, Frederick M.,Hussey, Gillian M.
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p. 8909 - 8913
(2007/10/03)
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- Dual responsive chemosensors for anions: The combination of fluorescent PET (Photoinduced Electron Transfer) and colorimetric chemosensors in a single molecule
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The design and synthesis of two novel fluorescent PET anion sensors is described, based on the principle of 'fluorophore-spacer-(anion)receptor'. The sensors 1 and 2 employ simple diaromatic thioureas as anion receptors, and the fluorophore is a naphthalimide moiety that absorbs in the visible part of the spectrum and emits in the green. Upon recognition of anions such as F- and AcO- in DMSO, the fluorescence emission of 1 and 2 was 'switched off', with no significant changes in the UV-vis spectra. This recognition shows a 1:1 binding between the receptor and the anions. In the case of F-, further additions of the anion, gave rise to large changes in the UV-vis spectra, where the λmax at 455 nm was shifted to 550 nm. These changes are thought to be due to the deprotonation of the 4-amino moiety of the naphthalimide fluorophore. This was in fact found to be the case, using simple naphthalimide derivatives such as 6. Sensors 1 and 2 can thus display dual sensing action; where at low concentrations, the fluorescence emission is quenched, and at higher concentrations the absorption spectra are modulated.
- Gunnlaugsson, Thorfinnur,Kruger, Paul E.,Lee, T. Clive,Parkesh, Raman,Pfeffer, Frederick M.,Hussey, Gillian M.
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p. 6575 - 6578
(2007/10/03)
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- The Synthesis of Alkylamino-N-alkylnaphthalic-1,8-imides from 2- and 4-nitronaphthalic Anhydrides by Nitro group Displacement
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4-Alkylamino-N-alkylnaphthalic-1,8-imides and 2-alkylamino isomers have been synthesised by the reaction of 4-nitro- and 2-nitronaphthalic anhydrides respectively with primary amines in aprotic solvents in which reaction the nitro group in 3-nitronaphthalic anhydride is unreactive. Unsymmetrical compounds in the 2- and 4-series are derived from either the appropriate 4-nitro-N-alkylnaphthalic-1,8-imide or for 4-dilakylamino compounds from 4-nitronaphthalic anhydride by reaction with a secondary amine and then the 4-dialkylaminonaphthalic anhydride with a primary amine.
- Alexiou, Michael S.,Tyman, John H. P.
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p. 632 - 652
(2007/10/03)
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- The UV-Visible Absorption and Fluorescence of some Substituted 1,8-Naphthalimides and Naphthalic Anhydrides
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A number of substituted 1,8-naphthalimides and naphthalic anhydrides have been prepared and their absorption and fluorescence properties in absolute ethanol have been determined.In the absence of an alkylamino substituent in the naphthalene ring, the compounds are colourless and weakly fluorescent.In the presence of such a substituent they become yellow and frequently fluoresce strongly with quantum yields of the order of 0.8.
- Alexiou, Michael S.,Tychopoulos, Vasiliki,Ghorbanian, Shohreh,Tyman, John H. P.,Brown, Robert G.,Brittain, Patrick I.
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p. 837 - 842
(2007/10/02)
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- IMPROVED NUCLEOPHILIC DISPLACEMENTS IN N-METHYL PYRROLIDINONE AS A SOLVENT
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The nucleophilic displacement reactions of 2- and 4-halogenonaphthalic-1,8-anhydrides and the N-imides, of 4,7-dichloroquinolines, the alkylation of lithio alkynes, the methylation of ethyl or methyl diacetylacetate and a variety of related reactions are greatly facilitated in N-methylpyrrolidinone as aprotic solvent.
- Tyman, John,Ghorbanian, Shoreh,Muir, M.,Tychopoulous, Vasiliki,Bruce, Ian,Fisher, Ian
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p. 179 - 188
(2007/10/02)
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- NUCLEOPHILIC DISPLACEMENT OF THE NITRO GROUP IN 2- AND 4-NITRONAPHTHALIC-1,8-ANHYDRIDES AND THEIR DERIVATIVES
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The nitro group in 2- and 4-nitronaphthalic-1,8-anhydrides can be substituted by amines in certain cases with retention of the anhydride grouping.
- Alexiou, Michael,Tyman, John,Wilson, Ian
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p. 2303 - 2306
(2007/10/02)
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