New Hosts Bearing Two Triphenylcarbinol Groups and Crystal Structures of Their Acetone Inclusion Compounds

Toda, Fumio; Kai, Akira; Toyotaka, Ritsuji; Yip, Wai-Hing; Mak, Thomas C. W.

doi:10.1246/cl.1989.1921

Cited by 20 publications

(29 citation statements)

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“…The bond lengths within the terphenyl group agree well with those found in the crystal structures of 2,2 00 -disubstituted derivatives of p-terphenyl (Lunazzi et al, 2005;Jones & Kuś, 2005;Debroy et al, 2009). Against expectation regarding the behaviour of (I) (Toda et al, 1989), growing crystals of diols (II) and (III) from ethanol yielded solvent-free crystals. Although both diol molecules crystallize in the triclinic crystal system (space group P1), in the crystal structure of (II) the molecule is located on a general position (Fig.…”

Section: Introductionsupporting

confidence: 81%

“…regarding the inclusion of organic solvents (Nangia, 2004;Caira & Nassimbeni, 1996). A prototype host compound of this kind is denoted (I) in Scheme 1 (Toda et al, 1989;Csö regh et al, 2004). Elongation of the central biphenyl axis in (I) by exchange for a 1,1 0 :4 0 ,1 00 -terphenyl group, as in (II), and in addition, substitution of the lateral phenyl groups of (II) by tolyl groups resulting in compound (III), should also lead to modified host-guest interaction and inclusion behaviour…”

Section: Introductionmentioning

confidence: 99%

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Two terphenyl-based diol hosts and corresponding solvent inclusions with dimethylformamide and acetonitrile

et al. 2015

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Having reference to an elongated structural modification of 2,2'-bis(hydroxydiphenylmethyl)biphenyl, (I), the two 1,1':4',1''-terphenyl-based diol hosts 2,2''-bis(hydroxydiphenylmethyl)-1,1':4',1''-terphenyl, C44H34O2, (II), and 2,2''-bis[hydroxybis(4-methylphenyl)methyl]-1,1':4',1''-terphenyl, C48H42O2, (III), have been synthesized and studied with regard to their crystal structures involving different inclusions, i.e. (II) with dimethylformamide (DMF), C44H34O2·C2H6NO, denoted (IIa), (III) with DMF, C48H42O2·C2H6NO, denoted (IIIa), and (III) with acetonitrile, C48H42O2·CH3CN, denoted (IIIb). In the solvent-free crystals of (II) and (III), the hydroxy H atoms are involved in intramolecular O-H···π hydrogen bonding, with the central arene ring of the terphenyl unit acting as an acceptor. The corresponding crystal structures are stabilized by intermolecular C-H···π contacts. Due to the distinctive acceptor character of the included DMF solvent species in the crystal structures of (IIa) and (IIIa), the guest molecule is coordinated to the host via O-H···O=C hydrogen bonding. In both crystal structures, infinite strands composed of alternating host and guest molecules represent the basic supramolecular aggregates. Within a given strand, the O atom of the solvent molecule acts as a bifurcated acceptor. Similar to the solvent-free cases, the hydroxy H atoms in inclusion structure (IIIb) are involved in intramolecular hydrogen bonding, and there is thus a lack of host-guest interaction. As a result, the solvent molecules are accommodated as C-H···N hydrogen-bonded inversion-symmetric dimers in the channel-like voids of the host lattice.

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Section: Introductionsupporting

confidence: 81%

Section: Introductionmentioning

confidence: 99%

Two terphenyl-based diol hosts and corresponding solvent inclusions with dimethylformamide and acetonitrile

et al. 2015

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“…Triphenylmethanol can act as a host towards guest molecules such as methanol and dimethyl sulfoxide (Weber, Skobridis & Goldberg, 1989) albeit with hydrogen-bonding arrangements wholly different from that in unsolvated Ph3COH. The diol mbis(diphenylhydroxymethyl)benzene, which forms similar host]guest aggregates with a range of different guest species, crystallizes as centrosymmetric dimers (Toda, Kai, Toyotaka, Yip & Mak, 1989) with graph set R~(16).…”

Section: Commentmentioning

confidence: 99%

Structures of 1-ferrocenyl-1-phenylethanol, ferrocenyl(diphenyl)methanol and ferrocene-1,1'-diylbis(diphenylmethanol)

Ferguson¹,

Gallagher²,

Glidewell³

et al. 1993

Acta Crystallogr C

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“…the replacement of the terminal aryl moieties by heteroaromatic units has been carried out. 17 Thereby, substitutions of phenyl groups in the parent structure 1 18,19 against 2-pyridyl or 2-thienyl residues ( Fig. 1) have been executed.…”

Section: Introductionmentioning

confidence: 99%

Crystalline Inclusion of Wheel-and-Axle Diol Hosts Featuring Benzo[b]thiophene Units as a Lateral Construction Element

Katzsch

Gruber

Weber

2015

Crystal Growth & Design

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By applying the 'wheel-and-axle' host concept and incorporating a previously developed heteroaromatic substitution strategy, a new type of diol hosts featuring two di(benzo [b]thien-2-yl)hydroxymethyl units attached to both ends of a central ethynylene (3) and 1,4-phenylene (4) moiety is reported. The syntheses of the host compounds are described and solvent inclusion formation via crystallization has extensively been studied showing a remarkable inclusion capability of the compounds. X-ray diffraction analysis of relevant crystal structures have been performed and comparatively discussed. Vapor sorption behavior of the compounds as solid receptor films coated on a quartz crystal microbalance considering a variety of solvent vapors has been scrutinized, indicating potential application as mass sensitive materials.3

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New Hosts Bearing Two Triphenylcarbinol Groups and Crystal Structures of Their Acetone Inclusion Compounds

Abstract: New hosts, m- and p-bis(diphenylhydroxymethyl)benzene and 2,2′-bis(diphenylhydroxymethyl)-1,1′-diphenyl, were found to exhibit high and selective inclusion tendencies toward a wide variety of guest compounds. Crystal structures of two representative acetone complexes were determined.

Cited by 20 publications

References 1 publication

Two terphenyl-based diol hosts and corresponding solvent inclusions with dimethylformamide and acetonitrile

Two terphenyl-based diol hosts and corresponding solvent inclusions with dimethylformamide and acetonitrile

Structures of 1-ferrocenyl-1-phenylethanol, ferrocenyl(diphenyl)methanol and ferrocene-1,1'-diylbis(diphenylmethanol)

Crystalline Inclusion of Wheel-and-Axle Diol Hosts Featuring Benzo[b]thiophene Units as a Lateral Construction Element

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