666829-83-0Relevant academic research and scientific papers
Programmed twisting of phenylene-ethynylene linkages from aromatic stacking interactions
Mullin, William J.,Pawle, Robert H.,Sharber, Seth A.,Müller, Peter,Thomas, Samuel W.
, p. 1198 - 1207 (2019/02/07)
Control over the conformation and packing of conjugated materials is an unsolved problem that prevents the rational design of organic optoelectronics, such as preventing self-quenching of luminescent molecules. Exacerbating this challenge is a general lack of widely applicable strategies for controlling packing with discrete, directional non-covalent interactions. Here, we present a series of conjugated molecules with diverse backbones of three or four arenes that feature pentafluorobenzyl ester substituents. Nearly all the compounds reveal intramolecular stacking interactions between the fluoroarene (ArF) side-chains and non-fluorinated arenes (ArH) in the middle of the chromophores; a twisted PE linkage accompanies each example of this intramolecular ArF-ArH stacking. Furthermore, these molecules can resist dramatic changes to emission upon transition from organic solution to thin film when ArF rings prevent interchromophore interactions. By broadening the structural space of conjugated backbones over which ArF-ArH stacking can twist PE linkages reliably and prevent self-quenching of solids with simple synthetic approaches, this work suggests fluorinated benzyl ester substituents adjacent to phenylene ethynylene linkages as supramolecular synthons for the crystal engineering of organic optoelectronic materials.
Gold-catalyzed C-S bond formation from thiols
Jean, Micka?l,Renault, Jacques,van de Weghe, Pierre,Asao, Naoki
supporting information; experimental part, p. 378 - 381 (2010/03/24)
ortho-Alkynylbenzoic acid alkyl esters act as alkylating agents of thiol derivatives with PPh3AuCl in combination with AgOTf in 1,2-dichloroethane at 80 °C. The corresponding sulfide compounds are obtained in good to excellent yields.
Synthesis of naphthalene derivatives through platinum(II)-catalyzed reaction of 2-alkynylbenzoates with vinyl ethers
Kusama, Hiroyuki,Funami, Hideaki,Iwasawa, Nobuharu
, p. 2014 - 2024 (2008/02/11)
A concise method for the preparation of 1-acyl-4-alkoxy- or 1-acyl-4-alkylsulfanylnaphthalenes has been developed by the PtCl 2-catalyzed reaction of o-ethynylbenzoates or benzothioates with vinyl ethers. Treatment of o-alkynylbenzoate derivatives with PtCl2 generated the platinum(II)-containing carbonyl ylides as a key reactive intermediate and these species reacted with vinyl ethers to give substituted naphthalenes in good yields. The presence of the platinum-containing carbonyl ylide was confirmed by NMR analyses of the mixture of o-ethynylbenzoate and [PtCl2(H2C=CH2)]2. Furthermore, it was suggested that the naphthalene derivatives were produced by [3+2] cycloaddition of the ylide species with vinyl ethers, followed by 1,2-alkyl migration of the generated platinum-carbene intermediates. Georg Thieme Verlag Stuttgart.
Platinum(II)-Catalyzed Reaction of 2-Alkynylbenzoates or Benzothioates with Vinyl Ethers: A Concise Method for Synthesis of 1-Acyl-4-alkoxy- or 1-Acyl-4-alkylsulfanylnaphthalene Derivatives
Kusama, Hiroyuki,Funami, Hideaki,Takaya, Jun,Iwasawa, Nobuharu
, p. 605 - 608 (2007/10/03)
(Matrix presented) A concise method for the preparation of 1-acyl-4-alkoxy- or 1-acyl-4-alkylsulfanylnaphthalenes has been developed by the reaction of o-ethynylbenzoates or benzothioates with vinyl ethers, in the presence of a catalytic amount of PtCl2. It is proposed that the reaction proceeds through [3 + 2]-cycloaddition of the platinum-containing carbonyl ylides followed by 1,2-alkyl migration.
