Supramolecular control of fluorinated benzophenones in the crystalline state

Schwarzer, Anke; Seichter, Wilhelm; Weber, Edwin; Stœckli-Evans, Helen; Losada, Martin; Hulliger, Jürg

doi:10.1039/b414556a

Cited by 51 publications

(49 citation statements)

References 27 publications

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“…The Br substitution seems to have the greatest effect on the packing. Although the N-phenyl non-fluorinated compound 13 shows the space group P2 1 /c, those being fluorinated crystallize in space groups C2/c (17), C2 (18), and enclathrate the solvent molecule (14ÁC 6 H 6 ) or resist suitable crystal formation (15,16). Moreover, influences of the placement and degree of fluorine substitution of the N-phenyl subunit on the space group of the crystal are observed.…”

Section: Isostructurality Calculationsmentioning

confidence: 90%

“…MS (ESI) m/z: 616 [M+H] + 100%. 3,4,5,methylidene]bicyclo[2.2.1]hept-2-ene-5,6-dicarboximide (18) N-(2,3,4,5,6-Pentafluorophenyl)maleimide (19f) (2.63 g, 10 mmol) and bis(4-bromophenyl)fulvene (20c) (3.90 g, 10 mmol) were used. Yield: 3.10 g (48%); mp: 237 8C (dec.).…”

Section: N-(4-fluorophenyl)-7(diphenylmethylidene)bicyclo[221]hept-mentioning

confidence: 99%

“…Within this frame, specific modes of organic fluorine involving weak interactions are considered to be rather effective, first and foremost applying to the ArÁ Á ÁAr F staking motif [5,14], while others are rated less distinct in their effectiveness (C-FÁ Á ÁH, C-FÁ Á ÁF and C-FÁ Á Áp F ) [15][16][17][18] thus causing sometimes a questioning of their existence [6,10,19]. However, a particular problem arises if further non-dominating interactions including weaker hydrogen bonds (O-HÁ Á Áp, C-HÁ Á Áp) [3,4] or XÁ Á ÁX contacts between the higher halogens [20] compete.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Involvement of organic fluorine substitution in the crystalline packing structures of tricyclic Diels–Alder adducts derived from diarylfulvenes and N-arylimides

Schwarzer

Bombicz

Weber

2010

Journal of Fluorine Chemistry

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Section: Isostructurality Calculationsmentioning

confidence: 90%

Section: N-(4-fluorophenyl)-7(diphenylmethylidene)bicyclo[221]hept-mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Involvement of organic fluorine substitution in the crystalline packing structures of tricyclic Diels–Alder adducts derived from diarylfulvenes and N-arylimides

Schwarzer

Bombicz

Weber

2010

Journal of Fluorine Chemistry

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“…The supramolecular assembly of rac-1 is similar to that of Dianins compound. [7] Dianins compound was found to be able to host a wide range of organic and inorganic guests, such as glycerol, argon, small carbohydrates, and SF 6 . It is useful in the storage and transport of volatile species.…”

mentioning

confidence: 99%

Supramolecular Assemblies of Chiral Propargylic Alcohols

et al. 2006

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Chiral propargylic alcohols are very useful synthetic precursors to many organic compounds.[1] A few propargylic alcohols were also found to form interesting supramolecular structures through intermolecular interactions of the hydroxy groups and the p electrons of the C C bonds.[2-4] Another supramolecular interaction based on the quadrupole p-p attraction between an aryl and a perfluoroaryl moiety was used to create new materials for applications in solid-state photopolymerization, liquid crystals, hydrogels, and so forth.[5] We have initiated a program to combine the four functional groups, including the aryl, perfluoroaryl, C C, and OH groups, to make the diaryl-substituted chiral propargylic alcohols and to explore their potential in supramolecular chemistry. Herein, we present some of findings that indicate that the presence of the functional groups not only makes the self-assembly of propargylic alcohols possible but it also allows for a finely tuned cooperation of interactions on a scale rarely seen in other supramolecular systems. We show herein that diaryl-substituted chiral propargylic alcohols can form cyclic hexameric supramolecular assemblies as a result of the cooperation between three major intermolecular forces: OÀ H···O hydrogen bonding, CÀH···FÀC hydrogen bonding involving organic fluorine atoms, and p-p stacking interactions between the pentafluorophenyl and phenyl rings. We believe that this synergy of intermolecular forces could be utilized in a variety of applications, including molecular recognition and discrimination.We synthesized the racemic propargylic alcohol rac-1 from the reaction of phenylacetylene with pentafluorobenzaldehyde in the presence of Et 2 Zn and HMPA at room

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“…Up to now a number of fluorinated compounds were synthesised to investigate phenylperfluorophenyl [2], HÁ Á ÁF [3], FÁ Á ÁF [4] and C-FÁ Á Áp F [5] interactions to study their influence on crystal structures [6,7].…”

Section: Introductionmentioning

confidence: 99%

A comparative study of crystal structures and inclusion properties of fluorinated triazines

Reichenbaecher¹,

Stœckli-Evans²,

Weber³

et al. 2006

Journal of Fluorine Chemistry

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Three perfluorinated host compounds of the triazine type, namely 2,4,6-tris(pentafluorophenoxy)-1,3,5-triazine (1), 2,4,6-tris(pentafluorothiophenoxy)-1,3,5-triazine (2) and 2,4,6-tris(pentafluorophenamin)-1,3,5-triazine (3), were synthesized differing only in the linking heteroatom (O, S and NH) between the triazine core and the pentafluorophenyl groups. The crystal structures involving compounds 1, 2 and their inclusion compounds are dominated by a variety of fluorine interactions (phenyl-perfluorophenyl, C-HÁ Á ÁF, FÁ Á ÁF, C-FÁ Á Áp F ). However, in the structure of 3, possessing additional hydrogen atoms of the linkage NH-groups, the formation of hydrogen bonds is favoured, whereas fluorine contacts are less apparent. Investigations by powder X-ray diffraction and thermogravimetric analysis revealed substantial differences in the host-guest interactions of the inclusion compounds.

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Supramolecular control of fluorinated benzophenones in the crystalline state

Cited by 51 publications

References 27 publications

Involvement of organic fluorine substitution in the crystalline packing structures of tricyclic Diels–Alder adducts derived from diarylfulvenes and N-arylimides

Involvement of organic fluorine substitution in the crystalline packing structures of tricyclic Diels–Alder adducts derived from diarylfulvenes and N-arylimides

Supramolecular Assemblies of Chiral Propargylic Alcohols

A comparative study of crystal structures and inclusion properties of fluorinated triazines

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