613-76-3Relevant articles and documents
Characterization of Push-Pull-Type Benzo[X]quinoline Derivatives (X = g or f): Environmentally Responsive Fluorescent Dyes with Multiple Functions
Fuchi, Yasufumi,Umeno, Tomohiro,Abe, Yuichiro,Ikeno, Keita,Yamasaki, Ryu,Okamoto, Iwao,Usui, Kazuteru,Karasawa, Satoru
, p. 13177 - 13190 (2020)
Benzo[X]quinoline (X = g or f: BQX) derivatives bearing bis-trifluoromethyl and amine groups have been designed as push-pull-type fluorescent dyes. Through the synthesis of BQX derivatives from 2,7-diaminonaphthalene, linear-type (BQL) and angular-type (BQA) structural isomers were obtained. X-ray structures of single crystals from six given BQX derivatives revealed that the BQL and BQA series adopt planar- and bowl-shaped structures. In the fluorescence spectra, interestingly, the BQL series emitted in the near-infrared region over 700 nm in polar solvents. Based on the visible absorptions and base properties related to the amine moiety, the ammonia responsiveness was investigated using an ion-exchange reaction by the BQX-HCl salt. By exploiting the environmentally responsive fluorescence probe, cell imaging through confocal laser microscopy was conducted using HeLa and 3T3-L1 cells, emitting specific lipid droplets. The results indicate that BQX derivatives have multiple functions and may be applied in materials chemistry and biochemistry.
Amination of oligofunctionalized dinaphthylmethanes: Factors affecting the reaction pathway
Maslennikova, Vera I.,Shelenkova, Lyudmila V.,Serkova, Olga S.,Vasyanina, Larisa K.,Nifantiev, Edward E.
, p. 136 - 149 (2013/01/16)
The reactions of oligofunctionalized 1,1-dinaphthylmethanes with primary amines and ammonia are described. In the reaction of amines with 2,2′,7,7′-tetrahydroxy- and 2,2′-dihydroxy-1,1- dinaphthylmethanes, the replacement of hydroxy groups by amino groups is accompanied by cleavage of C-C bonds and elimination of a methylene unit. The regiodirection of the process is determined by the number and the nature of substituents in the dinaphthylmethane core. The catalytic amination of 2,2′,7,7′-tetrakis(trifluoromethanesulfonyloxy)-1, 1-dinaphthylmethane is not accompanied by destruction of the dinaphthylmethane core. The reaction selectivity and the product structure depend on the nature of the aminating reagent. ARKAT-USA, Inc.
Intramolecular interactions in diiodonaphthalenes
Novak, Igor,Jiang, Huiming,Kovac, Branka
, p. 480 - 484 (2007/10/03)
The synthesis and the electronic structure of isomeric di-iodonaphthalenes is described. The electronic structure has been investigated by HeI/HeII photoelectron spectroscopy and non-Koopmans' quantum chemical calculations. The influence of the topology of iodine substitution on the electronic structure is discussed. Special emphasis is placed on elucidating the role of intramolecular iodine-iodine interactions.