1730-04-7Relevant academic research and scientific papers
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 Crystal Structure of Dimorphic Dibenzo[cde,opq]rubicene
Suresh, Joghee R.,Whitener, Glenn,Theumer, Gabriele,Br?cher, Dirk J.,Bauer, Ingmar,Massa, Werner,Kn?lker, Hans-Joachim
, p. 13759 - 13765 (2019)
Dibenzo[cde,opq]rubicene has been synthesized by an eight-step reaction sequence including an iron-mediated [2+2+1] cycloaddition and a flash vacuum pyrolysis as key steps. Two crystal modifications of the S-shaped, planar polycyclic aromatic hydrocarbon have been obtained and characterized by X-ray diffractometry.
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.
Facile synthesis of 1,8-naphthalimides in palladium-catalysed aminocarbonylation of 1,8-diiodo-naphthalene
Takács, Attila,ács, Péter,Kollár, László
, p. 983 - 987 (2008)
1,8-Diiodo-naphthalene was aminocarbonylated with various primary and secondary amines in the presence of palladium(0) complexes formed in situ from palladium(II) acetate and triphenylphosphine. In the case of primary amines, depending on the amine to substrate ratio, two types of products have been obtained in highly chemoselective reaction: dicarboxamides and N-substituted imides have been formed at high and low amine to substrate ratio, respectively. The reaction tolerates the ester functionality, so that amino acid esters could serve as N-nucleophiles and in this way, naphthalimides possessing stereogenic centre in the N-substituent could be synthesised.
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
Intramolecular [2 + 2] Photodimerization Achieved in the Solid State via Coordination-Driven Self-Assembly
Laird, Rebecca C.,Sinnwell, Michael A.,Nguyen, Nam P.,Swenson, Dale C.,Mariappan, S. V. Santhana,MacGillivray, Leonard R.
, p. 3233 - 3235 (2015)
(Figure Presented) An intramolecular [2 + 2] photocycloaddition is achieved in the organic solid state via self-assembly of Ag(I) ions and an endo-ditopic bipyridine. The cations aide to organize carbon-carbon double (C=C) bonds attached to the bipyridine for the cycloaddition reaction. The C=C bonds react regioselectively and quantitatively to afford a photoproduct with edge-sharing four-, five-, and six-membered rings. Our study demonstrates the first use of a metal-organic template to direct an intramolecular [2 + 2] photodimerization in the organic solid state.
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.
Mixed-Valent Molecular Triple Deckers
Schmidt, Hauke C.,Guo, Xingwei,Richard, Pascal U.,Neuburger, Markus,Palivan, Cornelia G.,Wenger, Oliver S.
supporting information, p. 11688 - 11691 (2018/09/10)
Two phenothiazine (PTZ) moieties were connected via naphthalene spacers to a central arene to result in stacked PTZ-arene-PTZ structure elements. Benzene and tetramethoxybenzene units served as central arenes mediating electronic communication between the two PTZ units. Based on cyclic voltammetry, UV/Vis-NIR absorption, EPR spectroscopy, and computational studies, the one-electron oxidized forms of the resulting compounds behave as class II organic mixed-valence species in which the unpaired electron is partially delocalized over both PTZ units. The barrier for intramolecular electron transfer depends on the nature of the central arene sandwiched between the two PTZ moieties. These are the first examples of rigid organic mixed-valent triple-decker compounds with possible electron-transfer pathways directly across a stacked structure, and they illustrate the potential of oligo-naphthalene building blocks for long-range electron transfer and a future molecular electronics technology.
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.
A robust microfluidic device for the synthesis and crystal growth of organometallic polymers with highly organized structures
Liu, Xiao,Yi, Qiaolian,Han, Yongzhen,Liang, Zhenning,Shen, Chaohua,Zhou, Zhengyang,Sun, Junliang,Li, Yizhi,Du, Wenbin,Cao, Rui
supporting information, p. 1846 - 1850 (2015/02/19)
A simple and robust microfluidic device was developed to synthesize organometallic polymers with highly organized structures. The device is compatible with organic solvents. Reactants are loaded into pairs of reservoirs connected by a 15 cm long microchannel prefilled with solvents, thus allowing long-term counter diffusion for self-assembly of organometallic polymers. The process can be monitored, and the resulting crystalline polymers are harvested without damage. The device was used to synthesize three insoluble silver acetylides as single crystals of X-ray diffraction quality. Importantly, for the first time, the single-crystal structure of silver phenylacetylide was determined. The reported approach may have wide applications, such as crystallization of membrane proteins, synthesis and crystal growth of organic, inorganic, and polymeric coordination compounds, whose single crystals cannot be obtained using traditional methods.
