20583-04-4Relevant academic research and scientific papers
Rapid and easy access to (E)-1,3-enynes, 1,3-diynes and allenes starting from propargylic acetals, exploiting the different reactivity of lithium and mixed lithium-potassium organometallic reagents
Blangetti, Marco,Deagostino, Annamaria,Rosso, Helena,Prandi, Cristina,Zavattaro, Chiara,Venturello, Paolo
, p. 5867 - 5874 (2007)
The treatment of propargylic acetals with various lithium and mixed lithium-potassium Schlosser reagents, has allowed a one-pot synthesis of (E)-1,3-enynes, 1,3-diynes and allenes, depending on the reaction conditions and the selected base. Various reacti
Photodimerization of anthracene derivatives in their neat solid state and in solid molecular compounds
Zouev,Cao, Den-Ke,Sreevidya,Telzhensky,Botoshansky,Kaftory
, p. 4376 - 4381 (2011)
The Cambridge Crystallographic Data Center provides valuable data for analysis and detection of compounds with potential to undergo photodimerization in the solid-state. Such analysis is presented for anthracene derivatives, and showed that there are many
Mechanosynthesis of Odd-Numbered Tetraaryl[n]cumulenes
Ardila-Fierro, Karen J.,Bolm, Carsten,Hernández, José G.
, p. 12945 - 12949 (2019/08/01)
A mechanochemical synthesis of one-dimensional carbon allotrope carbyne model compounds, namely tetraaryl[n]cumulenes (n=3, 5) was realized. Central for the mechanosynthesis of the cumulenic carbon nanostructures were the development of a mechanochemical Favorskii alkynylation-type reaction and the implementation of a solvent-free, acid-free reductive elimination with tin(II) chloride by ball milling.
Phosphorus-Containing Bis-allenes: Synthesis and Heterocyclization Reactions Mediated by Iodine or Copper Dibromide
Essid,Laborde,Legros,Sevrain,Touil,Rolland,Ayad,Volle,Pirat,Virieux
supporting information, p. 1882 - 1885 (2017/04/11)
Bisphosphorylallenes were easily obtained in multigram scale from the Wittig-type rearrangement of bispropargyl alcohols. Unlike other conjugated bis-allenes, these reagents underwent a double cyclization mediated by iodine or copper dibromide leading to the formation of bis-1,2-oxaphospholenes.
A Mechanistic Study of Halogen Addition and Photoelimination from π-Conjugated Tellurophenes
Carrera, Elisa I.,Lanterna, Anabel E.,Lough, Alan J.,Scaiano, Juan C.,Seferos, Dwight S.
supporting information, p. 2678 - 2689 (2016/03/12)
The ability to drive reactivity using visible light is of importance for many disciplines of chemistry and has significant implications for sustainable chemistry. Identifying photochemically active compounds and understanding photochemical mechanisms is important for the development of useful materials for synthesis and catalysis. Here we report a series of photoactive diphenyltellurophene compounds bearing electron-withdrawing and electron-donating substituents synthesized by alkyne coupling/ring closing or palladium-catalyzed ipso-arylation chemistry. The redox chemistry of these compounds was studied with respect to oxidative addition and photoelimination of bromine, which is of importance for energy storage reactions involving X2. The oxidative addition reaction mechanism was studied using density functional theory, the results of which support a three-step mechanism involving the formation of an initial η1 association complex, a monobrominated intermediate, and finally the dibrominated product. All of the tellurophene derivatives undergo photoreduction using 430, 447, or 617 nm light depending on the absorption properties of the compound. Compounds bearing electron-withdrawing substituents have the highest photochemical quantum efficiencies in the presence of an alkene trap, with efficiencies of up to 42.4% for a pentafluorophenyl-functionalized tellurophene. The photoelimination reaction was studied in detail through bromine trapping experiments and laser flash photolysis, and a mechanism is proposed. The photoreaction, which occurs by release of bromine radicals, is competitive with intersystem crossing to the triplet state of the brominated species, as evidenced by the formation of singlet oxygen. These findings should be useful for the design of new photochemically active compounds supported by main-group elements.
Unexpected molecular flip in solid-state photodimerization
Sreevidya, Thekku Veedu,Cao, Deng-Ke,Lavy, Tali,Botoshansky, Mark,Kaftory, Menahem
, p. 936 - 941 (2013/08/24)
Three cocrystals of the light-stable compound 1,1,6,6-tetraphenyl-2,4- hexadiyne-1,6-diol (I) with light-sensitive molecules 1,2-dimethyl-2(1H)- pyridinone (a), 6-methyl-2(1H)-pyridinone (b) and 2-methyl-2(1H)-pyridinone (c) were exposed to UV light. It w
A new tetraarylcyclopentadienone based low molecular weight gelator: Synthesis, self-assembly properties and anion recognition
Boiani, Mattia,Baschieri, Andrea,Cesari, Cristiana,Mazzoni, Rita,Stagni, Stefano,Zacchini, Stefano,Sambri, Letizia
body text, p. 1469 - 1478 (2012/07/31)
A new class of tetraarylcyclopentadienones bearing 3-hydroxy-1-propynyl substituents has been synthesized. One of them, 3,4-bis (4-(3-hydroxy-3- methylbut-1-ynyl) phenyl)-2,5-diphenylcyclopenta-2,4-dienone, exhibits pronounced aggregation properties in various organic solvents responding to thermal and ultrasound stimuli and represents the first example of a tetraarylcyclopentadienone based low molecular weight organogelator. The hydroxydimethyl group on the ethynyl substituent proved to be essential to perform the gelation process. The 1H NMR analysis and FT-IR spectroscopy suggested that the intermolecular π-π and hydrogen bonding interactions of the gelator with the solvent are the main driving forces for the supramolecular assembly. The SEM images of xerogels show the characteristic gelation morphologies of 3D fibrous network structures. Fluorescence and UV/Vis absorption studies provided more information to define the molecular packing model in the gelation state. In addition the obtained gels show selective response to the fluoride anion. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2012.
The rubrenic synthesis: The delicate equilibrium between tetracene and cyclobutene
Braga, Daniele,Jaafari, Abdelhafid,Miozzo, Luciano,Moret, Massimo,Rizzato, Silvia,Papagni, Antonio,Yassar, Abderrahim
scheme or table, p. 4160 - 4169 (2011/10/01)
Herein we describe the synthesis of new substituted tetraaryltetracenes, obtained by the dimerization of triarylchloroallenes, prepared from propargyl alcohols. The propargyl alcohols were prepared by two different synthetic strategies and then the alcohols were treated to obtain the corresponding acenes. In addition to the expected tetracene derivatives, we observed the formation of bis(alkylidene)cyclobutenes. When strong electron-donating substituents were present, the main product was the cyclobutene. We discuss a reaction mechanism that accounts for the formation of the cyclobutenes.
Kinetics of solid state photodimerization of 1,4-dimethyl-2-pyridinone in its molecular compound
Cao, Deng-Ke,Sreevidya, Thekku Veedu,Botoshansky, Mark,Golden, Gilad,Brown Benedict, Jason,Kaftory, Menahem
experimental part, p. 7377 - 7381 (2011/01/06)
The [4 + 4] photodimerization of 1,4-dimethyl-2-pyridinone (A) in its molecular compound with 1,1,6,6-tetraphenyl-2,4-hexadiyne-1,6-diol (I) was investigated by irradiation of a single crystal of the compound. The conversion to the product in a single-cry
Thermal cyclotrimerization of tetraphenyl[5]cumulene (tetraphenylhexapentaene) to a tricyclodecadiene derivative
Islam, Nazrul,Ooi, Takashi,Iwasawa, Tetsuo,Nishiuchi, Masaki,Kawamura, Yasuhiko
supporting information; experimental part, p. 574 - 576 (2009/06/17)
Tetraphenyl[5]cumulene (tetraphenylhexapentaene) underwent cyclotrimerization in refluxing toluene for 10-15 min to give a tricyclodecadiene derivative in 68% yield. The Royal Society of Chemistry.
