1012-73-3Relevant articles and documents
Synthesis of arylstannanes from arylamines
Chopa, Alicia B.,Lockhart, Maria T.,Silbestri, Gustavo
, p. 3358 - 3360 (2001)
Arylamines have been converted into aryltrimethylammonium salts, which on reaction with sodium trimethylstannide (1) in liquid ammonia afford aryltrimethylstannanes by the SRN1 mechanism. With (4-methoxyphenyl)- (2), (1-naphthyl)- (4), phenyl- (6), (4-acetylphenyl)- (8), and (4-cyanophenyl)trimethylammonium salts (10) the substitution products are obtained in good to excellent yields (45-100%). Also, the photo-stimulated reaction of (2-pyridyl)trimethylammonium iodide (12) with 1 leads to the substitution product 13 (50%). With (4-chlorophenyl)trimethylammonium iodide (14) the disubstitution product 19 is obtained in 76% yield. On the other hand, the results obtained in the reaction of (4-bromophenyl)trimethylammonium iodide (15) with 1 clearly indicate a fast HME reaction in the dark. The ET process (SRN1) competes, although inefficiently, under irradiation.
Selective synthesis of [6]-, [8]-, and [10]cycloparaphenylenes
Kayahara, Eiichi,Iwamoto, Takahiro,Suzuki, Toshiyasu,Yamago, Shigeru
, p. 621 - 623 (2013)
The selective synthesis of [6]-, [8]-, and [10]cycloparaphenylenes (CPPs) was achieved by a new synthetic route involving Ni(0)-mediated coupling of bis(para-haloaryl)dinuclear arylplatinum complexes and the reductive elimination of the complexes. Importantly, the highly strained [6]CPP was prepared in good overall yield.
Ortho-bridged perylene diimide dimer and preparation method thereof as well as application thereof in organic photovoltaic devices
-
Paragraph 0063-0065, (2020/07/23)
The invention provides an ortho-bridged perylene diimide dimer (formula I), a preparation method and an application thereof in the organic photovoltaic field. The invention further relates to an organic solar cell of the compound and a preparation method of the organic solar cell. Compared with a PDI monomer molecule, a formed twisted dimer structure is capable of effectively weakening excessive aggregation among PDI molecules, so that the phase size is reduced. Meanwhile, by virtue of ortho-bridging, the deformation of a PDI inner core caused by waist bridging can be avoided, so that certain planarity and relatively strong pi-pi accumulation can be maintained, and relatively high electronic mobility can be obtained. The PDI dimer is taken as a receptor material and is combined with an electron donor polymer so as to prepare the organic solar cell, so that very high photoelectric conversion efficiency is realized.
Visible-Light-Driven Synthesis of Arylstannanes from Arylazo Sulfones
Lian, Chang,Yue, Guanglu,Mao, Jinshan,Liu, Danyang,Ding, Yi,Liu, Zerong,Qiu, Di,Zhao, Xia,Lu, Kui,Fagnoni, Maurizio,Protti, Stefano
supporting information, p. 5187 - 5191 (2019/07/03)
The visible-light-driven preparation of (hetero)aryl stannanes was carried out under both photocatalyst- and metal-free conditions via irradiation of arylazo sulfones in the presence of hexaalkyldistannanes. The reaction shows a high efficiency and a wide substrates scope. The resulting crude organotin derivatives can be directly employed in a Stille protocol.
Influence of structural features of tri-functionalized aryl phosphates on the outcome of the SRN1 process with stannyl anions: A DFT study
Dorn, Viviana B.,Silbestri, Gustavo F.,Lockhart, María T.,Chopa, Alicia B.,Pierini, Adriana B.
, p. 1150 - 1156 (2013/06/27)
Under irradiation, 1,3-bis(diethoxyphosphoryloxy)-4-chlorobenzene (2), 1,4-bis(diethoxyphosphoryloxy)-3-chlorobenzene (3) and 1,3- bis(diethoxyphosphoryloxy)-5-chlorobenzene (4) react with trimethyltinsodium (1) in liquid ammonia giving entirely different distribution of stannylated products. These differences are explained through theoretical DFT studies. Experimental evidence for the involvement of an SRN1 mechanism was obtained.
Phenols as starting materials for the synthesis of arylstannanes via SRN11
Chopa, Alicia B.,Lockhart, María T.,Dorn, Viviana B.
, p. 1425 - 1429 (2008/10/08)
Phenols are converted into aryl diethyl phosphate esters (ArDEP), which on reaction with sodium trimethylstannide (1) or sodium triphenylstannide (2) in liquid ammonia afford arylstannanes by the SRN1 mechanism. Thus, the photostimulated reaction of phenylDEP (3), (4-methoxyphenyl)DEP (4), (4-biphenyl)DEP (5), (1-naphthyl)DEP (6), (2-naphthyl)DEP (7), and 2- (34), 3- (32), and (4-pyridyl)DEP (35) with 1 leads to monostannylated product in fair to excellent yields (20-98%). Also, substrates containing two or three leaving groups react with 1 under irradiation, affording the corresponding di- or tristannylated aryl compounds. With tetraethyl m-phenylene bisphosphate (15), tetraethyl p-phenylene bisphosphate (21), (4-chlorophenyl)DEP (22), and 1,3,5-tris(diethylphospho)benzene (30), the di- or trisubstitution products 1,3-bis(trimethylstannyl)benzene (19) (79%), 1,4-bis(trimethylstannyl)benzene (23) (95 and 97%), and 1,3,5-tris(trimethylstannyl)benzene (31) (57%) are obtained, respectively. Also, the reaction of 6 and 7 with 2 leads to substitution products in quantitative yields, and the reaction of 21, 22, and (4-bromophenyl)DEP (24) with 2 affords 1,4-bis(triphenylstannyl)benzene (38) in high yields (70-100%). On the other hand, the results obtained in the photostimulated reaction of 24 and (4-iodophenyl)DEP (25) with 1, as well as in the reaction of 25 with 2, clearly indicate a fast HME reaction.
Two-step synthesis of arylstannanes from phenols
Chopa, Alicia B.,Lockhart, Maria T.,Silbestri, Gustavo
, p. 2249 - 2250 (2008/10/08)
The reactions of a number of aryl diethyl phosphates (ArDEP) with (triphenylstannyl)sodium and (trimethylstannyl) sodium in liquid ammonia were studied. Results indicate that the conversion of phenols into the corresponding aryl diethyl phosphates followed by the S displacement with organotin anions is an excellent and convenient method for the synthesis of arylstannanes.
Novel organoborane Lewis acids via selective boron-tin exchange processes - Steric constraints to electrophilic initiation by the boron halide
Eisch, John J.,Kotowicz, Boguslaw W.
, p. 761 - 769 (2007/10/03)
With the purpose of preparing novel mono- and bidentate organoboron Lewis acids, the scope and limitations of synthesizing the requisite organoboranes by the boron-tin exchange between a boron halide and the appropriate organostannane have been examined in detail. The following organotin derivatives have been obtained either from the corresponding RMgBr or RLi reagent and MenSnCl4-n or from a Barbier procedure using the organic halide, Me3SnCl and magnesium metal: 1,2-bis(trimethylstannyl)ethyne, o-, m-, and p-bis(trimethylstannyl)benzenes, α,o-bis(trimethylstannyl)toluene, α,α-bis(trimethylstannyl)-o-xylene, and 2,2-dimethyl-2-stannaindane. The individual interaction of the 1,2-bis(trimethylstannyl)ethyne and the isomeric bis(trimethylstannyl)benzenes with Et2BBr produced the corresponding bis(diethylboryl)-derivatives. By contrast, with Et2BCl the α,o-bis(trimethylstannyl)toluene gave only o-diethylboryl-α-trimethylstannyltoluene and with BCl3 the α,α′-bis(trimethylstannyl)-o-xylene formed only α,α′-bis-(chlorodimethylstannyl)-o-xylene. Furthermore, in the attempted double boron-tin exchange between o-bis(trimethylstannyl)benzene and BCl3, an unprecedented rearrangement of the 1-(dichloroboryl)-2-(trimethylstannyl)benzene intermediate into its 1-[chloro(methyl)boryl]-2-(chlorodimethylstannyl) isomer was observed. Likewise, o-bis(trimethylstannyl)benzene with PhBCl2 produced by a similar rearrangement 1-[methyl(phenyl)boryl]-2-(chloro-dimethylstannyl)benzene. The thermolysis of such boranes led variously to definite dimers or ill-defined oligomers. Preliminary studies of the properties of these organoboranes have identified the heightened Lewis acidity of 1,2-bis(diethylboryl)ethyne and the π-electron delocalization involving the 2pΖ-boron orbitals in the 9,10-dihydro-9,10-diboraanthracene system. Finally, an electronic mechanism for the boron-tin exchange has been developed to account for the selectivity of the boron halide's attack at unsaturated carbon-tin bonds.
SYNTHESIS AND SPECTROSCOPIC CHARACTERISTICS OF ARYLTRIMETHYL-SILICON, -GERMANIUM, AND -TIN COMPOUNDS
Moerlein, S. M.
, p. 29 - 40 (2007/10/02)
The synthesis and spectroscopic characteristics of 28 para-substituted aryltrimethyl-silicon, -germanium, and -tin compounds are described.The infrared spectra show characteristic bands at 1245-1165 (methyl bend), 840-765 (methyl rock), and 1105-1020 (in-plane aromatic H bend) cm-1; the frequency of the last band was found to depend on the sum of the aromatic substituent masses, the presence or absence of metallic constituents in the substituent having little influence.The mass spectral fragmentation patterns are interpreted in terms of localization of positive charge on the metal atom, with subsequent bond cleavage behavior which obeys the rules for mass spectra of carbon compounds.
Substituent Effects and Perturbation of ?-Systems, XXXVI. Me3C-, Me3Si-, Me3Ge-, Me3Sn-, and Me3Pb-Substituted Benzene and Naphthalene Derivatives and Their Radical Anions
Kaim, Wolfgang,Tesmann, Holger,Bock, Hans
, p. 3221 - 3234 (2007/10/02)
The effects of substituents -X(CH3)3 (X=C, Si, Ge, Sn, Pb) in 1,4-disubstituted benzenes and naphthalenes are investigated: PE spectra and CT excitation energies yield the energy differences between the ground state of the neutral molecule M and the vario
