Synthesis and characterisation of 3- and 4-(pentafluorosulfanyl)benzoic acid derivatives

Zarantonello, C.; Guerrato, A.; Ugel, Elisabetta; Bertani, Roberta; Benetollo, Franco; Milani, Roberto; Venzo, Alfonso; Zaggia, Alessandro

doi:10.1016/j.jfluchem.2007.07.011

Cited by 16 publications

(8 citation statements)

References 17 publications

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“…The equatorial planes of the SF 5 group having an umbrella shape canting toward the fifth axial fluorine atom in all structures, as previously reported with the SF 5 group . The F ax and S atoms in structures of 2 , 3 , 7 , 11 , and 13 are coplanar with the adjacent aryl ring planes.…”

Section: Resultsmentioning

confidence: 96%

“…The sulfur atom of the SF 5 group has octahedral coordination geometry for both compounds. In 10 , the bond distances of S–F ax 1.570(5) Å; S–F eq 1.587(4), 1.604(4), 1.587(4), 1.564(4) Å; the bond angles of F ax –S–F eq 88.2(2), 88.0(3), 87.8(2), 88.8(2)°; F eq –S–F eq 89.8(2), 90.3(2), 89.5(2), 90.2(2)° and the C–S bond distance of 1.679(7) Å are comparable to that in the analogous 3-pentafluorosulfanylbenzoic acid, 3-acetamidopentafluorosulfanylbenzene, and 4-acetamidopentafluorosulfanylbenzene …”

Section: Resultsmentioning

confidence: 99%

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2,4-Diaryl-1,3-Chalcogen Azoles Bearing Pentafluorosulfanyl SF₅ Groups: A Synthetic and Structural Study

Hua

Slawin

et al. 2014

J. Org. Chem.

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A series of new 2,4-diaryl-1,3-chalcogen azoles having pentafluorosulfanyl SF5 functional groups has been prepared by means of the two-component cyclization of the selenoamide or thioamide with α-bromoketones. The selenoamides or thioamides were obtained from the reaction of Woollins' reagent or Lawesson's reagent with 4-pentafluorosulfanylbenzonitrile, followed by hydrolysis with water. All new compounds were characterized by (1)H, (13)C, (77)Se, (19)F NMR spectroscopy, and accurate mass measurement. X-ray crystal structure analysis of the selenoamide, thioamide, and 2,4-diarylpentafluorosulfanyl-1,3-chalcogen azoles reveal that the selenoamide and thioamide have very similar structural features along with similar intermolecular interactions such as the π-π stacking and the weak N-H···E (E = S or Se) hydrogen bonding. The 2,4-diarylpentafluorosulfanyl-1,3-chalcogen azoles show the newly formed five-membered N(1)-C(2)-E(3)-C(4)-C(5) ring is either perfectly planar (and coplanar with two peripheral aryl ring planes) or near-planar. The π-π intermolecular interactions and the weak C-H···π and C-H···X (X = Br, F, O) hydrogen bonding are discussed in the cases of 2,4-diarylpentafluorosulfanyl-1,3-chalcogen azoles.

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Section: Resultsmentioning

confidence: 96%

Section: Resultsmentioning

confidence: 99%

2,4-Diaryl-1,3-Chalcogen Azoles Bearing Pentafluorosulfanyl SF₅ Groups: A Synthetic and Structural Study

Hua

Slawin

et al. 2014

J. Org. Chem.

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“…After stirring for 3 d the mixture was extracted with hexane (0.5 mL × 3) and the combined extracts was analyzed by GC–MS to show the formation of 16e . The removal of the solvent gave as 16e 2,26,27 as a colorless oil (0.5 mg, 6 %).…”

Section: Methodsmentioning

confidence: 99%

Synergistic Effects of Lewis Bases and Substituents on the Electronic Structure and Reactivity of Boryl Radicals

2014

Chemistry A European J

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Boryl radicals have the potential for the development of new molecular entities and for application in new radical reactions. However, the effects of the substituents and coordinating Lewis bases on the reactivity of boryl radicals are not fully understood. By using first-principles methods, we investigated the spin-density distribution and reactivity of a series of boryl radicals with various substituents and Lewis bases. The substituents, along with the Lewis bases, only affect the radical reactivity when an unpaired electron is in the boron pz orbital, that is, for three-coordinate radicals. We found evidence of synergistic effects between the substituents and the Lewis bases that can substantially broaden the tunability of the reactivity of the boryl radicals. Among Lewis bases, pyridine and imidazol-2-ylidene show a similar capacity for stabilization by delocalizing the spin density. Electron-donating substituents, such as nitrogen, more efficiently stabilize boryl radicals than oxygen and carbon atoms. The reactivity of a boryl radical is always boron based, irrespective of the spin density on boron.

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“…For the isocyanoborate ligand, the C≡N and N–B distances are in the ranges of 1.14–1.15 and 1.55–1.56 Å, respectively, which are similar to those of other isocyanoborato complexes 17a], [17d] For the 4‐(pentafluorosulfanyl)phenyl isocyanide ligand in 6 , the SF 5 group adopts an octahedral geometry with typical S–F bond lengths of 1.57–1.59 Å, similar to those of other SF 5 ‐substituted organic compounds and metal complexes …”

Section: Synthesis and Characterizationmentioning

confidence: 99%

Luminescent Charge‐Neutral Copper(I) Phenanthroline Complexes with Isocyanoborate Ligand

Chan

Cheng

et al. 2018

Eur J Inorg Chem

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Copper(I) complexes with thermal activated delayed fluorescence (TADF) have attracted considerable attention for the development of emissive materials in organic light-emitting devices. However, many emissive Cu I complexes are cationic emitters and cannot be vacuum-sublimed, a process used for device fabrication. This has limited their applications in devices. In this work we have developed a series of emissive charge-There is a growing interest in the development of earth-abundant luminescent transition-metal complexes for a wide range of applications, including dye-sensitized solar cells, [1] oxygen sensors, [2] and organic light-emitting devices (OLEDs). [3] Although many luminescent precious-metal complexes have been demonstrated to show promising applications, [4] the exploration of earth-abundant luminescent transition-metal complexes for related applications would be highly desirable because of their sustainability. The much-less-explored first-row luminescent transition-metal complexes in comparison with second-and third-row complexes can be attributed to the presence of the low-lying nonradiative deactivating ligand-field excited state and nonradiative ligand reorganization deactivation processes, which could quench the emissive excited states.Copper(I) complexes have received considerable attention because of their closed-shell electronic configurations and their relatively small singlet-triplet splitting, which lead to their welldocumented thermal-activated delayed fluorescence (TADF). [5] Emission materials with TADF properties are of particular interest for OLED emissive materials as these materials are capable of harvesting both singlet and triplet excitons, which may improve the overall efficiency of the devices. Luminescent Cu I diimine complexes, such as those with sterically bulky ligands, for example, 2,9-dimethyl-1,10-phenanthroline (Me 2 phen), are an important class of luminescent Cu I complexes. The presence of sterically bulky substituents is essential for maintaining the emissive nature of these complexes as they can significantly [a] ] through the incorporation of a strong π-accepting anionic isocyanoborate ligand. All the complexes have been structurally characterized and their photophysical properties have been studied.

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Synthesis and characterisation of 3- and 4-(pentafluorosulfanyl)benzoic acid derivatives

Cited by 16 publications

References 17 publications

2,4-Diaryl-1,3-Chalcogen Azoles Bearing Pentafluorosulfanyl SF₅ Groups: A Synthetic and Structural Study

2,4-Diaryl-1,3-Chalcogen Azoles Bearing Pentafluorosulfanyl SF₅ Groups: A Synthetic and Structural Study

Synergistic Effects of Lewis Bases and Substituents on the Electronic Structure and Reactivity of Boryl Radicals

Luminescent Charge‐Neutral Copper(I) Phenanthroline Complexes with Isocyanoborate Ligand

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Synthesis and characterisation of 3- and 4-(pentafluorosulfanyl)benzoic acid derivatives

Cited by 16 publications

References 17 publications

2,4-Diaryl-1,3-Chalcogen Azoles Bearing Pentafluorosulfanyl SF5 Groups: A Synthetic and Structural Study

2,4-Diaryl-1,3-Chalcogen Azoles Bearing Pentafluorosulfanyl SF5 Groups: A Synthetic and Structural Study

Synergistic Effects of Lewis Bases and Substituents on the Electronic Structure and Reactivity of Boryl Radicals

Luminescent Charge‐Neutral Copper(I) Phenanthroline Complexes with Isocyanoborate Ligand

Contact Info

Product

Resources

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2,4-Diaryl-1,3-Chalcogen Azoles Bearing Pentafluorosulfanyl SF₅ Groups: A Synthetic and Structural Study

2,4-Diaryl-1,3-Chalcogen Azoles Bearing Pentafluorosulfanyl SF₅ Groups: A Synthetic and Structural Study