1730-04-7Relevant articles and documents
Structural distortions in diiodine-substituted unsaturated hydrocarbons
Bock, Hans,Sievert, Mark,Havlas, Zdenek
, p. 677 - 685 (1998)
1,10-Diiodophenanthrene, prepared for the first time by reacting I2 with dilithiophenanthrene, has a twist angle ω(I ··· C-C ··· I) = 63°between the two iodine centers and a distance d(I···I) = 3.61 A, which amounts to only 84% of the sum of van der Waals radii, 2r(I)(vdW) = 2 x 2.15 = 4.30 A. Based on an extensive literature search for distortions of carbon skeletons by repulsion between overlapping iodine substituents, the low-temperature structures of 2,2'-diiodobiphenyl (ω = 85°, d(I···I) = 4.35 A, 101% of 2r(I)(vdW)) and 1,8-diiodonaphthalene (ω = 2°to 17°, d(I···I) = 3.513.54 A, 82% of 2r(I)(vdW)) have also been determined. Density functional B3LYP calculations with 6-31G basis sets and 31G effective pseudopotentials for iodine provide information on an unexpectedly balanced charge distribution, leading to estimates of about 30 kJ mol-1 for the I/I repulsion and of about 10 kJ mol-1 for the reduced π delocalization in the extremely twisted skeleton of 1,10-diiodophenanthrene.
Synthesis and characterization of bis- N -2-Aryl Triazole as a fluorophore
Zhang, Yanwei,Ye, Xiaohan,Petersen, Jeffery. L.,Li, Minyong,Shi, Xiaodong
, p. 3664 - 3669 (2015)
Naphthalene-bridged bis-triazole (NBT) complexes were prepared and characterized for investigation of their photophysical properties. Unlike our previously reported N-2-aryl triazoles, which gave strong emissions through the planar intramolecular charge transfer mechanism (coplanar conformation), this newly developed NBT adopted a noncoplanar conformation between triazole and naphthalene, achieving fluorescence through twisted intramolecular charge transfer.
Saturated deep-blue emitter based on a spiro[benzoanthracene-fluorene]-linked phenanthrene derivative for non-doped organic light-emitting diodes
Liang, Houjie,Wang, Xinxin,Zhang, Xingye,Liu, Zhiyang,Ge, Ziyi,Ouyang, Xinhua,Wang, Suidong
, p. 4696 - 4701 (2014)
A spiro[benzoanthracene-fluorene] derivative containing a phenanthrene moiety, 2′,3-di(phenanthren-9-yl)spiro[benzo[de]anthracene-7,9′-fluorene] (DPSBAF), was prepared by a Suzuki coupling reaction. The photophysical and photochemical properties were investigated systematically. A non-doped organic light-emitting diode using DPSBAF as the emitter achieved a luminance efficiency of 2.18 cd A-1 with Commission Internationale de l'clairage 1931 chromaticity coordinates of (0.15, 0.09). The synthesized spiro[benzoanthracene-fluorene] derivative with a high thermal stability, a glass transition temperature of 210 °C and a decomposition temperature of 410 °C, shows potential for application in non-doped saturated deep-blue organic light-emitting diodes. This journal is
Peri interaction between selenium atoms in dinaphtho[1,8-b,c]-1,5-diselenocin and 1,8-bis(methylseleno)naphthalene
Fujihara,Yabe,Chiu,Furukawa
, p. 4345 - 4348 (1991)
A new symmetrical diselno peri-bridged naphthalene, dinaphtho[1,8-b,c]-1,5-diselenocin (1), and 1,8-bis(methylseleno)naphthalene (2) have been synthesized. The cyclic voltammogram of 1 and 2 showed one reversible oxidation peak with remarkably low oxidation potential. Selenide 1 in CHCl3 under air and scattered light undergoes oxidation to give the corresponding Se-oxide 11. The peri selenium-selenium interaction of 1 and 2 was found in electrochemical oxidation, in concentrated sulfuric acid, and in EI mass spectrum.
Transition-Metal-Free Decarboxylative Iodination: New Routes for Decarboxylative Oxidative Cross-Couplings
Perry, Gregory J. P.,Quibell, Jacob M.,Panigrahi, Adyasha,Larrosa, Igor
supporting information, p. 11527 - 11536 (2017/08/30)
Constructing products of high synthetic value from inexpensive and abundant starting materials is of great importance. Aryl iodides are essential building blocks for the synthesis of functional molecules, and efficient methods for their synthesis from chemical feedstocks are highly sought after. Here we report a low-cost decarboxylative iodination that occurs simply from readily available benzoic acids and I2. The reaction is scalable and the scope and robustness of the reaction is thoroughly examined. Mechanistic studies suggest that this reaction does not proceed via a radical mechanism, which is in contrast to classical Hunsdiecker-type decarboxylative halogenations. In addition, DFT studies allow comparisons to be made between our procedure and current transition-metal-catalyzed decarboxylations. The utility of this procedure is demonstrated in its application to oxidative cross-couplings of aromatics via decarboxylative/C-H or double decarboxylative activations that use I2 as the terminal oxidant. This strategy allows the preparation of biaryls previously inaccessible via decarboxylative methods and holds other advantages over existing decarboxylative oxidative couplings, as stoichiometric transition metals are avoided.
