15696-48-7Relevant academic research and scientific papers
SYNTHESIS OF 2,6-DIARYLPYRYLIUM TETRAFLUOROBORATES
Boiko, I.I.,Solntsev, Yu. N.,Krutikov, N. A.,Lutsik, V. P.,Boiko, T.N.
, p. 886 - 888 (1982)
A number of previously unknown 2,6-diarylpyrylium tetrafluoroborates was obtained by the reaction of substituted acetophenones with ethyl orthoformate and boron trifluoride etherate.
Structural and electronic properties of 2,2′,6,6′-tetraphenyl-dipyranylidene and its use as a hole-collecting interfacial layer in organic solar cells
Courté,Alaaeddine,Barth,Tortech,Fichou
, p. 487 - 492 (2017)
The accumulation of positive charges at the anodic interface considerably limits the efficiency of photovoltaic solar cells based on polymer/fullerene bulk heterojunctions (BHJs). Interfacial layers (IFLs) such as PEDOT:PSS improve charge injection but ha
Design of π -extended dipyranylidenes as redox-active materials
Courté, Marc,Fichou, Denis,Ng, Yong Xiang,Tang, Shasha
, (2021/07/02)
A series of novel tetrasubstituted dipyranylidenes (DIPO) consisting of large π-extended moieties located at the four edge of the quinoidal core were synthesized and characterized with UV–visible, photoluminescence spectroscopies and cyclic voltammetry. Tetraphenyldipyranylidene compound has a high molar absorption coefficient with ε = 8.73 × 104 l/mol.cm at 456 nm. Larger π-extended DIPO derivatives show a bathochromic absorption peak with lower molar absorption coefficient. In the presence of large π-extended moieties, these molecules present a higher first oxidation potential, leading to a deeper HOMO level. Remarkably, naphthyl, benzothienyl and benzofuryl-substituted DIPO show a third oxidation potential at 0.91 V, 0.99 V and 1.08 V respectively. These novel compounds which combined both aromatic and quinoidal characters are attractive for their applications as multiredox active materials.
Light and oxygen-enabled sodium trifluoromethanesulfinate-mediated selective oxidation of C-H bonds
Fu, Hua,Liu, Can,Liu, Yong,Yang, Haijun,Zhu, Xianjin
, p. 4357 - 4363 (2020/07/14)
Visible light-induced organic reactions are important chemical transformations in organic chemistry, and their efficiency highly depends on suitable photocatalysts. However, the commonly used photocatalysts are precious transition-metal complexes and elaborate organic dyes, which hamper large-scale production due to high cost. Here, for the first time, we report a novel strategy: light and oxygen-enabled sodium trifluoromethanesulfinate-mediated selective oxidation of C-H bonds, allowing high-value-added aromatic ketones and carboxylic acids to be easily prepared in high-to-excellent yields using readily available alkyl arenes, methyl arenes and aldehydes as materials. The mechanistic investigations showed that the treatment of inexpensive and readily available sodium trifluoromethanesulfinate with oxygen under irradiation of light could in situ form a pentacoordinate sulfide intermediate as an efficient photosensitizer. The method represents a highly efficient, economical and environmentally friendly strategy, and the light and oxygen-enabled sodium trifluoromethanesulfinate photocatalytic system represents a breakthrough in photochemistry. This journal is
Synthetic studies on a series of functionalized pyrylium salts, 4-chloro- and 4-bromophosphinines
Nagahora, Noriyoshi,Tokumaru, Hiroshi,Ikaga, Shinpei,Hanada, Takuya,Shioji, Kosei,Okuma, Kentaro
, p. 1880 - 1887 (2018/03/07)
A series of new pyrylium salts that bear sulfonate and phosphonate groups were obtained from the reactions between 2,6-diphenyl-4H-pyran-4-one, sulfonic anhydride, and chlorophosphates, and analyzed spectroscopically. Furthermore, treatment of 2,6-diphenyl-4H-pyran-4-one with phosphoryl chloride or bromide afforded the corresponding 4-chloro- and 4-bromopyrylium tetrafluoroborates in good yield. Subsequently, the synthesis of the corresponding 4-chloro- and 4-bromophosphinines was accomplished by treating the respective chloro- and bromopyrylium tetrafluoroborates with tris(trimethylsilyl)phosphine.
Pyrylenes: A New Class of Tunable, Redox-Switchable, Photoexcitable Pyrylium-Carbene Hybrids with Three Stable Redox-States
Antoni, Patrick W.,Hansmann, Max M.
supporting information, p. 14823 - 14835 (2018/11/02)
A new synthetic and modular access to a large family of redox-switchable molecules based upon the combination of pyrylium salts and carbenes is presented. The redox-properties of this new molecule class correlate very well with the π-accepting properties of the corresponding carbenes. While the pyrylium moiety acts as a chromophore, the carbene moiety can tune the redox-properties and stabilize the corresponding radicals. This leads to the isolation of the first monomeric pyranyl-radical in the solid-state. The three stable oxidation states could be cleanly accessed by chemical oxidation, characterized by NMR, EPR, UV-vis, and X-ray diffraction and supported by (TD)-DFT-calculations. The new hybrid class can be utilized as an electrochemically triggered switch and as a powerful photoexcited reductant. Importantly, the pyrylenes can be used as novel photocatalysts for the reductive activation of aryl halides and sulfonamides by consecutive visible light induced electron transfer processes.
Synthesis of bromo- and carboxylic acid-substituted methylenepyrans
Vologdin, Nikolay,Gauthier, Sebastien,Achelle, Sylvain,Caro, Bertrand,Guen, Francoise Robin-Le
, p. 606 - 614 (2014/07/21)
In this contribution we describe a series of pyranylidene derivatives bearing bromine atoms in various positions. Some of these bromo derivatives have been converted in carboxylic acid by halogen-metal exchange reaction using gaseous CO2 as electrophile. Selected compounds have been studied by UV-visible absorption and cyclic voltametry to study the influence of the substituent on the pyranylidene core.
Dye-sensitized solar cells based on novel diphenylpyran derivatives
Bolag, Altan,Nishida, Jun-Ichi,Hara, Kohjiro,Yamashita, Yoshiro
supporting information; experimental part, p. 510 - 511 (2011/08/05)
We have prepared a series of novel diphenylpyran derivatives as photosensitizers of dye-sensitized solar cells (DSSCs) for the first time. Nonsubstituted dye 3a shows an energy conversion efficiency of 2.3% and iodine-substituted dye 3d shows a higher eff
Ethynyl Carbocations. VI. Heterocyclization of 1,5-Diaryl-3-phenylethynyl-1,5-pentanediones
Koblik, A. V.,Murad'yan, L. A.
, p. 254 - 257 (2007/10/03)
Heterocyclization of 1,5-diaryl-3-phenylethynyl-1,5-diketones involves either both keto groups to give 4-phenylethynylpyrylium salts or the ethynyl moiety and one of the phenacyl fragments with elimination of aryl methyl ketone to give pyrylium salts containing no substituents in position 4.
Ethynyl Carbocations. V. Synthesis and Properties of 4-Phenylethynyl-4H-pyrans
Koblik, A. V.,Murad'yan, L. A.
, p. 245 - 253 (2007/10/03)
A method for preparation of 4-phenylethynyl-4H-pyrans was developed, and their reactions with acid reagents, resulting in 4-phenylethynylpyrylium salts and 1,5-diketones containing ethynyl and allene moieties, were studied.Conditions for nucleophilic addi
