883-99-8Relevant articles and documents
Aggregation-Induced Emission (AIE) Fluorophore Exhibits a Highly Ratiometric Fluorescent Response to Zn2+ in vitro and in Human Liver Cancer Cells
Mehdi, Hassan,Gong, Weitao,Guo, Huimin,Watkinson, Michael,Ma, Hua,Wajahat, Ali,Ning, Guiling
, p. 13067 - 13075 (2017)
Two novel organic fluorophores, containing bis-naphthylamide and quinoline motifs, have been designed and synthesized. One of the fluorophores contains an isobutylene unit and exhibits a significant aggregation-induced emission (AIE) and a remarkable highly selective ratiometric fluorescence response towards Zn2+ in solution as well as in human liver cancer cells. The AIE behavior of this fluorophore was fully verified by fluorescence and UV/Vis spectroscopy, quantum yield calculations, and single-crystal X-ray diffraction, which revealed an intricate crystal packing system. Conversely, a fluorophore that lacks the isobutylene moiety did not exhibit any significant fluorescent properties as a result of its more flexible molecular structure that presumably allows free intramolecular rotational processes to occur.
Cyclodimerization and Diels-Alder reaction of a spiroepoxycyclohexadienone with an o-quinodimethane structure
Bonnarme, Vincent,Mondon, Martine,Cousson, Alain,Gesson, Jean-Pierre
, p. 1143 - 1144 (1999)
Oxidation of 3-hydroxymethyl-2-naphthol with periodate affords a single exo-syn dimer arising from the intermediate ortho quinonoid spiroepoxycyclohexadienone; the latter can also be trapped by reactive dienophiles.
Synthesis and Clathrates of Oligomeric 2-O-Naphthoide Macrocycles
AlHujran, Tayel A.,Dawe, Louise N.,Collins, Julie,Georghiou, Paris E.
, p. 971 - 973 (2011)
New macrocyclic O-naphthoides 4-6 were synthesized from dehydration reactions of 3-hydroxy- and 7-tertbutyl- 3-hydroxy-2-naphthoic acids, respectively. Their X-ray structures were determined and their clathrate inclusion properties were investigated. Hexamer 6 formed an inclusion clathrate with four chloroform molecules. The trimer 5, by analogy with tri-o-thymotide, was studied for its potential optical resolution effects.
Two new fluorescent Zn2+ sensors exhibiting different sensing mode with subtle structural changes
Mehdi, Hassan,Pang, Hongchang,Gong, Weitao,Wajahat, Ali,Manivannan, Kalavathi Dhinakaran,Shah, Shaheen,Ye, Jun-Wei,Ning, Guiling
, p. 378 - 386 (2017)
Two novel receptors HL-1 and HL-2 without and with hydroxyl groups were designed and synthesised. Both receptors showed highly selective coordination towards Zn2+ and exhibited diverse sensing behaviour due to the structural variations. HL-1 showed monotonous ‘turn-on’ response towards Zn2+ while HL-2 displayed highly Zn2+ sensitive ‘turn on’ and ‘ratiometric’ properties. Detailed Job plot experiment, single crystal data, 1H NMR, ESI-MS, UV–vis and density functional theory calculation studies were conducted to understand the binding modes of HL-1 and HL-2 with Zn2+. These results revealed the binding stoichiometric ratio between receptors and Zn2+ were 1:1 with low detection limits and high binding constants.
Naphthaldehyde-derived ligands: Synthesis and their Ni(II) ion complexation
Al-Said, Naim H.,Mizyed, Shehadeh,Al-Sehemi, Abdullah G.,Kleeb, Amani M.
, p. 275 - 279 (2014)
Three novel diazacrown ether ligands, namely 17-, 18-, and 20-membered O2N2-donor macrocycles derived from 3,3′-[butane-1, 4-diylbis(oxy)]bis(2-naphthalenecarbaldehyde), were prepared and characterized by 1H and 13C NMR spectroscopy and mass spectra. Their host-guest interaction with Ni(II) was studied in DMSO-d 6 using 1H NMR spectroscopy. The stoichiometry of the complex in each case in the concentration range examined was determined to be 1:1 using the continuous variation method (Job's plot). The 17-membered O2N2-donor macrocycle in which the two nitrogen atoms are tethered by three methylene units binds Ni(II) more strongly than the other two macrocycles do. Graphical abstract: [Figure not available: see fulltext.]
Enantioselective Synthesis of 3,3′-Disubstituted 2-Amino-2′-hydroxy-1,1′-binaphthyls by Copper-Catalyzed Aerobic Oxidative Cross-Coupling
Zhao, Xiao-Jing,Li, Zi-Hao,Ding, Tong-Mei,Tian, Jin-Miao,Tu, Yong-Qiang,Wang, Ai-Fang,Xie, Yu-Yang
supporting information, p. 7061 - 7065 (2021/02/27)
A challenging direct asymmetric catalytic aerobic oxidative cross-coupling of 2-naphthylamine and 2-naphthol, using a novel CuI/SPDO system, has been successfully developed for the first time. Enantioenriched 3,3′-disubstituted NOBINs were achieved and could be readily derived to divergent chiral ligands and catalysts. This reaction features high enantioselectivities (up to 96 % ee) and good yields (up to 80 %). The DFT calculations suggest that the F–H interactions between CF3 of L17 and H-1,8 of 2-naphthol, and the π–π stacking between the two coupling partners could play vital roles in the enantiocontrol of this cross-coupling reaction.
A highly selective colorimetric and fluorescent probe for quantitative detection of Cu2+/Co2+: The unique ON-OFF-ON fluorimetric detection strategy and applications in living cells/zebrafish
Wang, Zhi-Gang,Wang, Yang,Ding, Xiao-Jing,Sun, Yu-Xuan,Liu, Hai-Bo,Xie, Cheng-Zhi,Qian, Jing,Li, Qing-Zhong,Xu, Jing-Yuan
, (2019/11/26)
Identifying and detecting similar target cations through combining “turn on” and “turn off” fluorescence mechanism is effective and challenging. Now a new colorimetric and ON-OFF-ON fluorescent probe N′-((7-(diethylamino)-2-oxo-2H-chromen-3-yl)methylene)-3-hydroxy-2-naphthohydrazide (L) was reported, which could detect Cu2+ and Co2+ in phosphate buffered CH3CH2OH-H2O solvent system. With the assistance of glutathione and pH adjustment, a unique ON-OFF-ON fluorescence detection strategy could be achieved for distinguishing Cu2+ and Co2+. The emission of probe could recover from the L-Cu2+ and L-Co2+ system by addition of GSH or adjusting pH value to 4, respectively, which is due to the abolishment of paramagnetic Cu2+/Co2+. Based on fluorescence titration experiments, the limit of detection was determined as 3.84 × 10?9 M and 4.55 × 10?9 M for Cu2+ and Co2+, respectively. Meanwhile, the detection limit reached 6.21 × 10?8 M for Cu2+ and 6.96 × 10?8 M for Co2+ according to absorbance signal output. Fast recognition of Cu2+/Co2+ can be achieved by obvious color changes from green to colorless under UV light, as well as from yellow to orange-red in room light. The binding mode of L toward Cu2+ and Co2+ have been systematically studied by Job's plot analysis, ESI-MS, IR and density functional theory calculations. Most strikingly, further practical applications of the probe L in fluorescence imaging were investigated in MCF-7 cells and zebrafish due to its low cytotoxicity and good optical properties, suggesting that L could serve as a fluorescent sensor for tracking Cu2+ and Co2+ in vivo.