501-60-0Relevant articles and documents
Photomechanical Control of the Electronic Properties of Linear π-Conjugated Systems
Jousselme, Bruno,Blanchard, Philippe,Gallego-Planas, Nuria,Levillain, Eric,Delaunay, Jacques,Allain, Magali,Richomme, Pascal,Roncali, Jean
, p. 5297 - 5306 (2003)
Photodynamic molecular architectures have been synthesized by covalent fixation of a photoisomerizable dimethylazobenzene group at two fixed points of conformationally flexible π-conjugated quater- and sexithiophene chains. Theoretical geometry optimizati
Photoswitchable Conjugated Oligoelectrolytes for a Light-Induced Change of Membrane Morphology
Bazan, Guillermo C.,Leifert, Dirk,Limwongyut, Jakkarin,Mikhailovsky, Alexander A.,Moreland, Alex S.
, p. 20333 - 20337 (2020)
The synthesis of a new conjugated oligoelectrolyte (COE), namely DSAzB, is described, which contains a conjugated core bearing a diazene moiety in the center of its electronically delocalized structure. Similar to structurally related phenylenevinylene-based COEs, DSAzB readily intercalates into model and natural lipid bilayer membranes. Photoinduced isomerization transforms the linear trans COE into a bent or C-shape form. It is thereby possible to introduce DSAzB into the bilayer of a cell and disrupt its integrity by irradiation with light. This leads to controlled permeabilization of membranes, as demonstrated by the release of calcein from DMPG/DMPC vesicles and by propidium iodide influx experiments on S. epidermidis. Both experiments support that the permeabilization is selective for the light stimulus, highly efficient, and repeatable. Target-selective and photoinduced actions demonstrated by DSAzB may have broad applications in biocatalysis and related biotechnologies.
Synthesis and Hg2+ recognition of novel azobenzene derivatives bearing heterocyclic units
Gao, Yan,Song, Jian,Wang, Wei
, p. 146 - 148 (2012)
Four novel azobenzene derivatives, 4,4'-bis(CH2SAr)azobenzene (Ar = different heterocyclic units), have been prepared and characterised by IR, 1H NMR, 13C NMR, MS and elemental analysis. Their complexation properties to di
Optical Control of Cardiac Function with a Photoswitchable Muscarinic Agonist
Riefolo, Fabio,Matera, Carlo,Garrido-Charles, Aida,Gomila, Alexandre M. J.,Sortino, Rosalba,Agnetta, Luca,Claro, Enrique,Masgrau, Roser,Holzgrabe, Ulrike,Batlle, Montserrat,Decker, Michael,Guasch, Eduard,Gorostiza, Pau
, p. 7628 - 7636 (2019)
Light-triggered reversible modulation of physiological functions offers the promise of enabling on-demand spatiotemporally controlled therapeutic interventions. Optogenetics has been successfully implemented in the heart, but significant barriers to its u
H2O2-mediated room temperature synthesis of 2-arylacetophenones from arylhydrazines and vinyl azides in water
Luo, Mengqiang,Zhang, Yaohong,Fang, Ping,Li, Yan,Qi, Chenze,Li, Yong,Shen, Runpu,Cheng, Kai,Wang, Hai
supporting information, p. 630 - 635 (2022/02/01)
An environmentally benign, cost-efficient and practical methodology for the room temperature synthesis of 2-arylacetophenones in water has been discovered. The facile and efficient transformation involves the oxidative radical addition of arylhydrazines with α-aryl vinyl azides in the presence of H2O2 (as a radical initiator) and PEG-800 (as a phase-transfer catalyst). From the viewpoint of green chemistry and organic synthesis, the present protocol is of great significance because of using cheap, non-toxic and readily available starting materials and reagents as well as amenability to gram-scale synthesis, which provides an attractive strategy to access 2-arylacetophenones.
Photoinduced, Copper-Catalyzed Enantioconvergent Alkylations of Anilines by Racemic Tertiary Electrophiles: Synthesis and Mechanism
Cho, Hyungdo,Suematsu, Hidehiro,Oyala, Paul H.,Peters, Jonas C.,Fu, Gregory C.
supporting information, p. 4550 - 4558 (2022/03/18)
Transition-metal catalysis of substitution reactions of alkyl electrophiles by nitrogen nucleophiles is beginning to emerge as a powerful strategy for synthesizing higher-order amines, as well as controlling their stereochemistry. Herein, we report that a readily accessible chiral copper catalyst (commercially available components) can achieve the photoinduced, enantioconvergent coupling of a variety of racemic tertiary alkyl electrophiles with aniline nucleophiles to generate a new C-N bond with good ee at the fully substituted stereocenter of the product; whereas this photoinduced, copper-catalyzed coupling proceeds at -78 °C, in the absence of light and catalyst, virtually no C-N bond formation is observed even upon heating to 80 °C. The mechanism of this new catalytic enantioconvergent substitution process has been interrogated with the aid of a wide array of tools, including the independent synthesis of proposed intermediates and reactivity studies, spectroscopic investigations featuring photophysical and EPR data, and DFT calculations. These studies led to the identification of three copper-based intermediates in the proposed catalytic cycle, including a chiral three-coordinate formally copper(II)-anilido (DFT analysis points to its formulation as a copper(I)-anilidyl radical) complex that serves as a persistent radical that couples with a tertiary organic radical to generate the desired C-N bond with good enantioselectivity.
Selective Oxidation of Anilines to Azobenzenes and Azoxybenzenes by a Molecular Mo Oxide Catalyst
Han, Sheng,Cheng, Ying,Liu, Shanshan,Tao, Chaofu,Wang, Aiping,Wei, Wanguo,Yu, Han,Wei, Yongge
supporting information, p. 6382 - 6385 (2021/02/09)
Aromatic azo compounds, which play an important role in pharmaceutical and industrial applications, still face great challenges in synthesis. Herein, we report a molybdenum oxide compound, [N(C4H9)4]2[Mo6O19] (1), catalyzed selective oxidation of anilines with hydrogen peroxide as green oxidant. The oxidation of anilines can be realized in a fully selectively fashion to afford various symmetric/asymmetric azobenzene and azoxybenzene compounds, respectively, by changing additive and solvent, avoiding the use of stoichiometric metal oxidants. Preliminary mechanistic investigations suggest the intermediacy of highly active reactive and elusive Mo imido complexes.
