Perfluoro-1,1′-biphenyl and perfluoronaphthalene and their derivatives as π-acceptors for anions

Yi, Hai; Albrecht, Markus; Valkonen, Arto

doi:10.1039/c4nj01654h

Cited by 22 publications

(19 citation statements)

References 43 publications

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“…Derivatives of decafluorobiphenyl and octafluoronaphthalene could act as acceptors for an anion due to anion−π interaction. 6 Polyfluorinated oxacalixarenes, which are potential macrocyclic molecules to make “guest–host” complexes, have been synthesized by reaction of perfluoro- m -xylene with tetrafluororesorcinol. 7 Aiming for use as organic conductors in printable electronics, perfluoroterphenyl derivatives were synthesized and studied for potential self-assembly using X-ray crystallography.…”

Section: Introductionmentioning

confidence: 99%

Reactions of Bifunctional Perfluoroarylsilanes with Activated C–F Bonds in Perfluorinated Arenes

Nishida

Fukaya

et al. 2019

ACS Omega

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Reactions of bifunctional perfluoroarylsilanes, p- and m-C6F4(SiMe3)2 as well as o-BrC6F4SiMe3, with substituted perfluoroarenes having electron-withdrawing groups were investigated using NMR and density functional theory calculation techniques. The C–F bond in perfluoroarenes was activated by the para-position of an electron-withdrawing group, such as CF3, C6F5, CN, and NO2. The reaction of C6F4(SiMe3)2 mainly occurred at the para-position of the perfluoroarenes and also occurred at the ortho-position of C6F5CN and C6F5NO2. Two equivalent reactions of perfluoroarenes with bifunctional p- and m-C6F4(SiMe3)2 provided disubstituted perfluoroarenes, along with a small amount of protonated monosubstituted perfluoroarenes. The reaction of o-BrC6F4SiMe3 with the CF3- and CN-substituted pentafluorobenzenes provided unexpected coupling products between C–Br and C–F bonds, in addition to the coupling products between C–SiMe3 and C–F bonds.

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Section: Introductionmentioning

confidence: 99%

Reactions of Bifunctional Perfluoroarylsilanes with Activated C–F Bonds in Perfluorinated Arenes

Nishida

Fukaya

et al. 2019

ACS Omega

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“…Particularly, but not exclusively, the rigidity of these compounds is interesting for applications in crystal engineering, 6 , 7 metal–organic frameworks (MOFs), 8 polymers of intrinsic microporosity (PIMs), 9 , 10 organic polymers of intrinsic microporosity (OMIMs), 11 and supramolecular chemistry. 12 In our group different polyfluorinated polyphenyl compounds have served as scaffold for halogen bond donors to build up structures for molecular recognition 13 and halogen bond mediated catalysis. 14 In these studies, the fluorine substituents play an important role since they ensure strong halogen bonds due to the electron withdrawing nature of the fluorine atoms.…”

Section: Introductionmentioning

confidence: 99%

“…One example is the development of liquid crystalline materials, which are important for liquid crystal displays (LCDs). − Perfluorinated biphenyls have also been considered for the development of organic light emitting diodes (OLEDs) and organic semiconductors, making use of their electronic properties. Particularly, but not exclusively, the rigidity of these compounds is interesting for applications in crystal engineering, , metal–organic frameworks (MOFs), polymers of intrinsic microporosity (PIMs), , organic polymers of intrinsic microporosity (OMIMs), and supramolecular chemistry . In our group different polyfluorinated polyphenyl compounds have served as scaffold for halogen bond donors to build up structures for molecular recognition and halogen bond mediated catalysis .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Polyflourinated Biphenyls; Pushing the Boundaries of Suzuki–Miyaura Cross Coupling with Electron-Poor Substrates

Bulfield

Huber

2017

J. Org. Chem.

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Polyfluorinated biphenyls are interesting and promising substrates for many different applications. Unfortunately, all current methods for the syntheses of these compounds only work for a hand full of molecules or only in very special cases. Thus, many of these compounds are still inaccessible to date. Here we report a general strategy for the synthesis of a wide range of highly fluorinated biphenyls. In our studies we investigated crucial parameters, such as different phosphine ligands and the influence of various nucleophiles and electrophiles with different degrees of fluorination. These results extend the scope of the already very versatile Suzuki–Miyaura reaction toward the synthesis of very electron-poor products, making these more readily accessible. The presented methodology is scalable and versatile without the need for elaborate phosphine ligands or Pd-precatalysts.

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“…In this work, a pentagon-octagon-pentagon (5-8-5) defect in a 6 Â 6 graphene super-cell was constructed, as this kind of DG may be expected to have metallic or outstanding optoelectronic properties. In addition, to reveal the interactions between the built 5-8-5 DG and molecules, four organic donor/acceptor (D/A) molecules [27][28][29][30][31] including TTF, FNa, TCNQ and F4TCNQ were selected and non-covalently introduced to the DG. A series of structures and properties including geometry, interaction energy, Mulliken charge distribution, terahertz frequency vibration, visualization of the interactions in real space, charge density difference, electronic transition behaviour, band structure and DOS were calculated to reveal the non-covalent interactions.…”

Section: Introductionmentioning

confidence: 99%

Revealing the interactions between pentagon–octagon–pentagon defect graphene and organic donor/acceptor molecules: a theoretical study

Liu

Xie

et al. 2015

Phys. Chem. Chem. Phys.

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Defect engineering and the non-covalent interaction strategy allow for dramatically tuning the optoelectronic features of graphene. Herein, we theoretically investigated the intrinsic mechanism of non-covalent interactions between pentagon-octagon-pentagon (5-8-5) defect graphene (DG) and absorbed molecules, tetrathiafulvalene (TTF), perfluoronaphthalene (FNa), tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ), through geometry, distance, interaction energy, Mulliken charge distribution, terahertz frequency vibration, visualization of the interactions, charge density difference, electronic transition behaviour, band structure and density of state. All the calculations were performed using density functional theory including a dispersion correction (DFT-D). The calculated results indicate that the cyano- (CN) group (electron withdraw group) in TCNQ and F4TCNQ, rather than the F group, gain the electron from DG effectively and exhibit much stronger interactions via wavefunction overlap with DG, leading to a short non-covalent interaction distance, a large interaction energy and a red-shift of out-of-plane terahertz frequency vibration, changing the bands near the Fermi level and enhancing the infrared (IR) light absorption significantly. The enhancement of such IR absorbance offering a broader absorption (from 300 to 1200 nm) will benefit light harvesting in potential applications of solar energy conversion.

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Perfluoro-1,1′-biphenyl and perfluoronaphthalene and their derivatives as π-acceptors for anions

Cited by 22 publications

References 43 publications

Reactions of Bifunctional Perfluoroarylsilanes with Activated C–F Bonds in Perfluorinated Arenes

Reactions of Bifunctional Perfluoroarylsilanes with Activated C–F Bonds in Perfluorinated Arenes

Synthesis of Polyflourinated Biphenyls; Pushing the Boundaries of Suzuki–Miyaura Cross Coupling with Electron-Poor Substrates

Revealing the interactions between pentagon–octagon–pentagon defect graphene and organic donor/acceptor molecules: a theoretical study

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