95966-33-9Relevant academic research and scientific papers
A New, Highly Potent 1,8-Naphthalimide-based Fluorescence “Turn off” Chemosensor Capable of Cu2+ Detection in China's Yellow River Water Samples
Aderinto, Stephen Opeyemi
, p. 1432 - 1445 (2017)
A new 1,8-naphthalimide-based fluorescence “turn off” chemosensor, N-phenyl-4-(3,3′-((2-aminoethyl)azanediyl)dipropanoic acid)-1,8-naphthalimide (MAST), for the detection of Cu2+ was synthesized. Upon treatment with Cu2+, in coexistence with various competitive metal ions in HEPES-buffered dimethylsulfoxide (DMSO) solution (v/v, 1:1; pH 7.4), MAST displayed a high selectivity toward Cu2+ with a fluorescence quenching of 83.67%. Additionally, a good linear response of MAST for the detection of Cu2+ was obtained in the concentration range of 10 × 10?6 to 50 × 10?6 M. A 1:1 stoichiometric interaction of MAST with Cu2+ was observed, and the association constant and detection limit were calculated to be 1.37 × 106 and 0.69 × 10?8 M, respectively. The sensing mechanism of the chemosensor toward Cu2+ was proposed due to the effect of the paramagnetic nature of Cu2+ and reverse-photo-induced electron transfer (PET) process. Ultimately, the proposed chemosensor was applied to quantify Cu2+ in real-world water samples, with excellent recovery rates of 98.00–109.80% observed.
Aggregation-induced emission or aggregation-caused quenching? Impact of covalent bridge between tetraphenylethene and naphthalimide
Ma, Xiaoxie,Chi, Weijie,Han, Xie,Wang, Chao,Liu, Shenghua,Liu, Xiaogang,Yin, Jun
supporting information, p. 1790 - 1794 (2021/03/08)
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.
Quantitative and systematic designing of fluorophores enables ultrasensitive distinguishing carbonyls
Chen, Yu,Li, Yunyu,Mao, Wenle,Shi, Lei,Xia, Wei,Yan, Chenxu,Yang, Lixiang,Zhang, Lingfan,Zhang, Wenqing
, p. 12661 - 12668 (2021/07/25)
Although the use of sophisticated fluorescent probes can improve the detection sensitivity, either the lack of quantitative design for fluorophores or the deficiency of selectivity towards individual species makes it extremely difficult to distinguish homologs accurately. Herein, this study reports a quantitative strategy for the systematic engineering of fluorophoresviadensity functional theory (DFT). A series of seven 1,8-naphthylamide hydrazine (NH-1-7) compounds was elaborately tailored on the basis of the PET mechanism, EPS charge population and the maximum HOMO overlap principle. The results showed that the obtainedNH-4exhibited 300-fold “off-on” signal towards carbonyls with extraordinary reactivity and high solubility. Importantly, the ultra-low limits of detection (LOD) towards multi-carbonyl homologs could reach 1.0 × 10?12M on the ultra-high pressure liquid chromatography (UHPLC) in an 8 min analysis window. This systematic and quantitative engineering of fluorophores lays a bridge between efficient development of novel fluorophores and trace level detection in various matrixes.
NOVEL NATHTHALIMIDE-BENZOTHIAZOLE BASED COMPOUNDS AND CHEMOSENSOR FOR SELECTIVE DETECTION OF CYANIDE ION AND TRYPTOPHAN AMINO ACID COMPRISING THE SAME
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Paragraph 0096; 0099-0102, (2020/11/05)
The present invention relates to a novel naphthalimide-benzocyazole compound and a method for detecting cyanide ion and tryptophan amino acid using the same. The naphthalimide-benzocyazole compound has improved sensitivity and selectivity with respect to harmful cyanide ion and tryptophan amino acid existing in an aqueous solution. Therefore, a chemical sensor using the same can selectively detect cyanide ion and tryptophan amino acid in a water-soluble assay sample by more quickly and simply confirming colorimetric or fluorescent signals.
Evaluation of fluorogenic aminonaphthalenesulfonamides and 6-hydrazinobenz[de]isoquinoline-1,3-diones for the detection of bacteria
Luo, Jia Lin,Jin, Terry,Váradi, Linda,Perry, John D.,Hibbs, David E.,Groundwater, Paul W.
, p. 15 - 26 (2015/10/29)
New fluorogenic enzyme substrates were synthesized by the coupling of aminonaphthalenesulfonamides or 6-hydrazinobenz[de]isoquinoline-1,3-diones with β-alanine. The 6-hydrazinobenz[de]isoquinoline-1,3-diones were also condensed with a range of aryl aldehydes to give the corresponding hydrazones. The photophysical properties of the synthesized amines and hydrazines and their amide, hydrazide and hydrazone derivatives, were examined and they were also incorporated into Columbia agar in order to determine their potential for the detection of pathogenic bacteria.
Synthesis of 4-amino substituted 1,8-naphthalimide derivatives using palladium-mediated amination
Fleming, Cassandra L.,Ashton, Trent D.,Pfeffer, Frederick M.
, p. 135 - 143 (2014/06/23)
Successful amination of 4-bromo-1,8-naphthalimides with 'lengthy' imide N-functionality has been achieved using a general palladium mediated approach (conventional thermal protocols were sub-optimal). Only readily available Pd/ligand combinations were considered and the resulting Buchwald-Hartwig procedure using Pd2(dba)3, Xantphos and Cs 2CO3 is high yielding, relatively mild (40-80 °C, 24 h, yields 50-90%), requires only a modest excess of amine (3.0 equiv) and works equally well with other imide N-substituents. As such, the protocol complements existing methods but is superior for more complex substrates. Herein we compare this Pd mediated approach to the methods most commonly used and further demonstrate its utility by synthesising a number of new, highly fluorescent, 4-aminonaphthalimides.
Water-solvent method for the synthesis of N-substituted and N-,4-disubstituted 1,8-naphthalimides under microwave irradiation
Zhang, Ye,Feng, Shao-Bo,Wang, Kai,Yi, Xiang-Hui,Wang, Heng-Shan,Pan, Ying-Ming
experimental part, p. 3042 - 3052 (2012/08/14)
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.
Design and synthesis of some 1,8-naphthalimides as fluorescence probes for transition metal ions
Wang, Yingchun,Zhang, Ye,Yi, Xianghui,Qin, Wen
experimental part, p. 323 - 326 (2012/08/07)
Some 1,8-naphthalimide derivatives (4a-4d) were designed and synthesized from 1,8-naphthalic anhydride and their structures were characterized by 1H NMR, MS and elementary analysis. Then their fluorescence probes for five transition metal ions Cd2+, Co2+, Cu2+, Ni2+ and Zn2+ was investigated by fluorescence titration, respectively. The results showed that compound 4a can available and selectively probe for cobalt(II) ion, with quenching constant (KSV) 6.37 × 10 3 L mol1 and binding constants (Ka) 3.03 × 10 3 L mol1, respectively.
An efficient naphthalimide based fluorescent dyad (ANPI) for F- and Hg2+ mimicking OR, XNOR and INHIBIT logic functions
Shahid, Mohammad,Srivastava, Priyanka,Misra, Arvind
, p. 1690 - 1700 (2011/10/04)
A fluorescent bischromophoric dyad combining anthracene and naphthalic anhydride units has been synthesized and characterized. The dyad shows a FRET mediated emission signal at ～535 nm when excited at λex. = 380/360 nm, with efficient energy transfer efficiency (ET = 93%) and quantum yield (Φ = 0.155). Upon interaction with F- and Hg 2+ ions selectively, a diminished (switched-Off) FRET signal is observed and the naked-eye sensitive color of the solution changed to dark red with enhanced emission corresponding to an anthracene moiety (switched-On). Job's plot analysis revealed a 1:1 stoichiometry between dyad and F -/AcO- and Hg2+ ions. The output fluorescence signals exhibited by dyad on chemical inputs of F-, AcO- and Hg2+ ions mimicked OR, XNOR and INHIBIT logic functions. A 1H NMR titration experiment suggested deprotonation of -NH proton and "Y-type or tweezer-like" H-bonding interaction in the presence of F- and AcO-, respectively, involving -NH, -CHN- and anthracene ring protons.
Microwave-assisted synthesis and evaluation of naphthalimides derivatives as free radical scavengers
Zhang, Ye,Feng, Shaobo,Wu, Qiang,Wang, Kai,Yi, Xianghui,Wang, Hengshan,Pan, Yingming
experimental part, p. 752 - 759 (2012/05/20)
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.
