28442-30-0Relevant academic research and scientific papers
Highly Fluorinated Trianglimine Macrocycles: A Supramolecular Organic Framework
Kunde, Tom,Pausch, Tobias,Reiss, Guido J.,Schmidt, Bernd M.
, p. 161 - 165 (2022)
A novel highly fluorinated dialdehyde was prepared by a two-stage synthesis. This reactive building block for dynamic imine chemistry was used in a condensation reaction to generate the first extensively fluorinated trianglimine. An analysis of the material properties and, especially, the crystal structure of the [3+3] macrocycle revealed a supramolecular organic framework with tubular porous channels. The use of fluorinated ligands to generate hydrophobic electron-deficient channel-like pores is an important addition to the ever-expanding field of supramolecular networks and to trianglimine chemistry in general.
A fluorine-containing hydrophobic covalent triazine framework with excellent selective CO2 capture performance
Wang, Guangbo,Leus, Karen,Jena, Himanshu Sekhar,Krishnaraj, Chidharth,Zhao, Shuna,Depauw, Hannes,Tahir, Norini,Liu, Ying-Ya,Van Der Voort, Pascal
, p. 6370 - 6375 (2018)
In this article, a set of fluorine functionalized covalent triazine-based frameworks have been designed and synthesized with 2,2′,3,3′,5,5′,6,6′-octafluoro-4,4′-biphenyldicarbonitrile as the monomer under typical ionothermal conditions. A prominent defluorination process during synthesis etches the networks to release CFn, resulting in a significant loss of fluorine and carbon. Notably, the synergistic effects of polar C-F bonds and rich CO2-philic N sites bestow upon the framework an excellent H2 uptake (1.77 wt%, 77 K and 1 bar) as well as a significantly high CO2 adsorption capacity (5.98 mmol g-1, at 273 K and 1 bar), surpassing all related CTF materials measured under identical conditions that have been reported in the literature to date. Additionally, the material also exhibits a high CO2/N2 selectivity of 31 as predicted by the Henry model. The hydrophobicity of the CTF materials has been significantly enhanced owing to the incorporation of hydrophobic fluorine groups, which was further confirmed by ambient water vapor sorption.
Condensed-ring aryl compound, organic electronic device, and application thereof
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Paragraph 0048-0050, (2020/03/17)
The invention provides a condensed-ring aryl compound, an organic electronic device, and an application thereof. The compound has the structure represented as the formula (I) or (II), wherein X1, X2 and Y1 are independently selected from a combination of a connecting bond, N and CR6, the ring A and the ring B are in a conjugated structure, any one of the R1 to R4 and the R6 are independently connected to the ring A the ring B via a single bond or a double bond, and/or the any adjacent two among the R1 to R4 and the R6 form a ring C, being an electron-withdrawing ring, the R5 is selected from aconnection bond, R7-substituted or -non-substituted C6-C30 aryl groups, and R7-substituted or -non-substituted C2-C30 heteroaryl groups, and the R1 to R4, R6 and R7 are electron-withdrawing groups. The compound is free of intramolecular stacking and can prolong service life of the device, wherein the substituent groups are electron-withdrawing groups, and the compound has LUMO energy level of -4.6 to -6.0 eV. The compound can serve as a P-doping material.
The Synthesis of Organic Molecules of Intrinsic Microporosity Designed to Frustrate Efficient Molecular Packing
Taylor, Rupert G. D.,Bezzu, C. Grazia,Carta, Mariolino,Msayib, Kadhum J.,Walker, Jonathan,Short, Rhys,Kariuki, Benson M.,McKeown, Neil B.
supporting information, p. 2466 - 2472 (2016/02/18)
Efficient reactions between fluorine-functionalised biphenyl and terphenyl derivatives with catechol-functionalised terminal groups provide a route to large, discrete organic molecules of intrinsic microporosity (OMIMs) that provide porous solids solely by their inefficient packing. By altering the size and substituent bulk of the terminal groups, a number of soluble compounds with apparent BET surface areas in excess of 600m2 g-1 are produced. The efficiency of OMIM structural units for generating microporosity is in the order: propellane>triptycene>hexaphenylbenzene>spirobifluorene>naphthyl=phenyl. The introduction of bulky hydrocarbon substituents significantly enhances microporosity by further reducing packing efficiency. These results are consistent with findings from previously reported packing simulation studies. The introduction of methyl groups at the bridgehead position of triptycene units reduces intrinsic microporosity. This is presumably due to their internal position within the OMIM structure so that they occupy space, but unlike peripheral substituents they do not contribute to the generation of free volume by inefficient packing.
Superhydrophobic perfluorinated metal-organic frameworks
Chen, Teng-Hao,Popov, Ilya,Zenasni, Oussama,Daugulis, Olafs,Miljanic, Ognjen S.
supporting information, p. 6846 - 6848 (2013/07/26)
Three perfluorinated Cu-based metal-organic frameworks (MOFs) were prepared starting from extensively fluorinated biphenyl-based ligands accessed via C-H functionalization. These new materials are highly hydrophobic: with water contact angles of up to 151
Perfluorozinc aromatics by direct insertion of zinc into C-F or C-CL bonds
Miller, Alexey O.,Krasnov, Vyacheslav I.,Peters, Dietmar,Platonov, Vyacheslav E.,Miethchen, Ralf
, p. 3817 - 3819 (2007/10/03)
For the first time perfluoroaromatic organozinc compounds were obtained by direct action of zinc on C-F bonds in the presence of metal salts (SnCl2, CuCl2, ZnBr2). The reactions are accelerated by ultrasound. The scope of
Aromatic radical-anions. XII. A cyclic amperometric and ESR study of the transformations of polyfluorinated benzonitrile radical-anions
Efremova, N. V.,Starichenko, V. F.,Shteingarts, V. D.
, p. 47 - 56 (2007/10/02)
Cyclic voltamperometry and ESR spectrometry were used to study the chemical transformations of radical-anions of benzonitrile derivatives containing from two to five fluorine atoms.Two types of transformations were found to be characteristic for such species, namely, the elimination of a fluoride anion and subsequent formation of defluorination products and dimerization with the subsequent formation of fluorinated derivatives of 4,4'-dicyanodiphenyl.The facility of these processes depends significantly on the number and arrangement of the fluorine atoms in the benzene ring.The relationship between the electronic structure and reactivity of fluorinated benzonitrile radical-anions was examined.
