9,9′-Bianthracenyl

Kyzioł, Janusz B.; Zaleski, Jacek

doi:10.1107/s160053680700339x

Cited by 13 publications

(12 citation statements)

References 2 publications

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“…Single crystals of compounds 1 – 3 , and 5 were obtained and the structures were determined using X‐ray diffraction 11. Crystallographic data for 9,9′‐bianthryl ( 4 ) were previously reported 12. The molecular structures of the series of sulfur‐bridged anthracenes 1 – 3 are qualitatively similar with only minor differences observed in the solid‐state geometries.…”

Section: Methodssupporting

confidence: 56%

Oxidation‐State‐Dependent Photochemistry of Sulfur‐Bridged Anthracenes

et al. 2013

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Section: Methodssupporting

confidence: 56%

Oxidation‐State‐Dependent Photochemistry of Sulfur‐Bridged Anthracenes

et al. 2013

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“…1Í5 In each molecule, the two anthracene planes are nearly perpendicular (dihedral angle 80.5°) 6 and the rotation about the C9ÍC9¤ bond is considerably restricted. 7 These structural features facilitate the formation of cavities for guest molecules upon assembly.…”

mentioning

confidence: 99%

Molecular Structure of Chlorocycloheptane in Inclusion Compound with 9,9′-Bianthryl and Gelation during Crystallization

Toyota¹,

Okamoto²,

Ishikawa³

et al. 2009

Bulletin of the Chemical Society of Japan

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9,9¤-Bianthryl formed an inclusion compound with chlorocycloheptane in a 2:1 ratio. X-ray analysis revealed that two guest molecules were accommodated in a cavity surrounded by eight host molecules. The guest molecules were conformationally fixed in each cavity into either of two twist-chair forms that differed in the position of the chloro group. These conformations were compared with the calculated ones for chlorocycloheptane itself by DFT calculation. When the inclusion compound was prepared from a concentrated solution of 9,9¤-bianthryl in chlorocycloheptane, the gelation was followed by crystallization. This phenomenon is unusual for relatively small molecules lacking strong intermolecular interactions.9,9¤-Bianthryl (1) and related compounds are found to form inclusion compounds with a wide range of small organic molecules. 1Í5 In each molecule, the two anthracene planes are nearly perpendicular (dihedral angle 80.5°) 6 and the rotation about the C9ÍC9¤ bond is considerably restricted.7 These structural features facilitate the formation of cavities for guest molecules upon assembly. X-ray structures of inclusion compounds of 9,9¤-bianthryl so far reported reveal that guest molecules are occasionally accommodated in cavities in a less stable conformation to fit the cavity size and shape.3Í5 For example, chlorocyclohexane (2) form an inclusion compound with 1 in the axial conformation (Scheme 1), 4 which is less stable than the equatorial conformation, 8 while this guest molecule is included by another host derived from tartaric acid in the equatorial conformation.9 Conformational analysis of cycloheptane derivatives is more complicated than that of cyclohexane derivatives because of facile interconversions around several possible conformers.10 Even in the inclusion compound with tris(5-acetyl-3-thienyl)methane, cycloheptane molecules are significantly disordered even at 220 K.11 Therefore, we employed this unique hydrocarbon host to elucidate the conformation of cycloheptanes in crystal cavities, and used chlorocycloheptane (3) as a typical monosubstituted cycloheptane for this purpose. We herein report the X-ray structure of the inclusion compound focusing on the mode of inclusion and the conformation of seven-membered ring moieties. We also found an interesting phenomenon, gelation of a solution of 9,9¤-bianthryl in chlorocycloheptane, during the preparation of

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“…[11] Crystallographic data for 9,9'-bianthryl (4) were previously reported. [12] The molecular structures of the series of sulfurbridged anthracenes 1-3 are qualitatively similar with only minor differences observed in the solid-state geometries. The intramolecular anthracene-anthracene centroid (An-An) distance remains relatively constant throughout the series (1 = 5.100 , 2 = 4.984 , 3 = 5.019 ), and the through space distance between the bridge-head carbons are all about 2.9 .…”

mentioning

confidence: 61%