Chromotropisms of Imidazole Derivatives. III. Crystal Structure of 4,5-Bis(4-methoxyphenyl)-2-(4-nitrophenyl)-1<i>H</i>-imidazole

Inouye, Yoshinobu; Sakaino, Yoshiko

doi:10.1246/bcsj.59.3295

Cited by 16 publications

(9 citation statements)

References 2 publications

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“…Host-guest binding events detected by colour changes resulting from associated conformational changes and thus shifts in energy of electronic transitions have been reported for a few imidazole compounds 7 and boronic acid derivatives. 8 We have reported the synthesis and guest-responsive colour changes of chromogenic host compounds, 3-{2-[2-(3-hydroxy-3,3-diphenyl-prop-1-ynyl)-phenylazo]-phenyl}-1,1-diphenylprop-2-yn-1-ol (1), 3-{3-[3-(3-hydroxy-3,…”

Section: Introductionmentioning

confidence: 95%

Chromogenic guest-responsive host compounds which allow rapid guest screening

et al. 2002

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Azo host compounds undergo rapid and clearly visible colour changes from yellow to bright orange/red on complexation with guest molecules, while no colour change is noted in the absence of complexation. This provides a rapid screening method for potential guest compounds as the first step towards the development of guest specific host compounds for use in sensors relying only on a simple, visible colour change readout mechanism.

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Section: Introductionmentioning

confidence: 95%

Chromogenic guest-responsive host compounds which allow rapid guest screening

et al. 2002

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“…The detection of host:guest binding events by colour changes resulting from associated conformational changes and thus shifts in energy of electronic transitions have been reported for a few imidazole compounds. 5 In an earlier communication we reported the synthesis and guest responsive colour changes of a chromogenic host compound, 3-{4-[4-(3-hydroxy-3, 3-diphenylprop-1-ynyl)phenylazo]phenyl}-1,1-diphenylprop-2-yn-1-ol 3. 6 We now report the preparation and complexation behaviour of a further two host compounds in this series, namely, 3-{2-[2-(3-hydroxy-3,3-diphenylprop-1-ynyl)phenylazo]phenyl}-1,1-diphenylprop-2-yn-1-ol 1 and 3-{3-[3-(3-hydroxy-3,3-diphenylprop-1-ynyl)phenylazo]phenyl}-1,1-diphenylprop-2-yn-1-ol 2.…”

Section: Introductionmentioning

confidence: 99%

Novel chromogenic, guest-sensitive host compounds

2002

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“…The chemistry of lophine derivatives has a long history in relation to important physicochemical phenomena such as chemiluminescence through its oxidation and photo-, piezoand thermochromic properties (Zimmerman et al, 1961;Maeda & Hayashi, 1969, 1970. Only a few imidazole analogues or nitro derivatives of lophine are known (Inouye & Sakaino, 1985, 1986Sakaino, Fujii et al, 1990;Sakaino, Shimizu et al, 1990;Kaftory et al, 1998;Bu et al, 2003). The spectral properties of lophine derivatives are of interest: the colour change is dependent on the solvation in the crystal and in different derivatives.…”

Section: Commentmentioning

confidence: 99%

Structural comparisons between methylated and unmethylated nitrophenyl lophines

Yanover

Kaftory

2009

Acta Crystallogr C

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The lophine derivative 2-(2-nitrophenyl)-4,5-diphenyl-1H-imidazole, C21H15N3O2, (I), crystallized from ethanol as a solvent-free crystal and from acetonitrile as the monosolvate, C21H15N3O2.C2H3N, (II). Crystallization of 2-(4-nitrophenyl)-4,5-diphenyl-1H-imidazole from methanol yielded the methanol monosolvate, C21H15N3O2.CH4O, (III). Three lophine derivatives of methylated imidazole, namely, 1-methyl-2-(2-nitrophenyl)-4,5-diphenyl-1H-imidazole methanol solvate, C22H17N3O2.CH4O, (IV), 1-methyl-2-(3-nitrophenyl)-4,5-diphenyl-1H-imidazole, C22H17N3O2, (V), and 1-methyl-2-(4-nitrophenyl)-4,5-diphenyl-1H-imidazole, C22H17N3O2, (VI), were recrystallized from methanol, acetonitrile and ethanol, respectively, but only (IV) produced a solvate. Compounds (III) and (IV) each crystallize with two independent molecules in the asymmetric unit. Five imidazole molecules in the six crystals differ in their molecular conformations by rotation of the aromatic rings with respect to the central imidazole ring. In the absence of a methyl group on the imidazole [compounds (I)-(III)], the rotation angles are not strongly affected by the position of the nitro group [44.8 (2) and 45.5 (1) degrees in (I) and (II), respectively, and 15.7 (2) and 31.5 (1) degrees in the two molecules of (III)]. However, the rotation angle is strongly affected by the presence of a methyl group on the imidazole [compounds (IV)-(VI)], and the position of the nitro group (ortho, meta or para) on a neighbouring benzene ring; values of the rotation angle range from 26.0 (1) [in (VI)] to 85.2 (1) degrees [in (IV)]. This group repulsion also affects the outer N-C-N bond angle. The packing of the molecules in (I), (II) and (III) is determined by hydrogen bonding. In (I) and (II), molecules form extended chains through N-H...N hydrogen bonds [with an N...N distance of 2.944 (5) A in (I) and 2.920 (3) A in (II)], while in (III) the chain is formed with a methanol solvent molecule as the mediator between two imidazole rings, with O...N distances of 2.788 (4)-2.819 (4) A. In the absence of the imidazole N-H H-atom donor, the packing of molecules (IV)-(VI) is determined by weaker intermolecular interactions. The methanol solvent molecule in (IV) is hydrogen bonded to imidazole [O...N = 2.823 (4) A] but has no effect on the packing of molecules in the unit cell.

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Chromotropisms of Imidazole Derivatives. III. Crystal Structure of 4,5-Bis(4-methoxyphenyl)-2-(4-nitrophenyl)-1H-imidazole

Cited by 16 publications

References 2 publications

Chromogenic guest-responsive host compounds which allow rapid guest screening

Chromogenic guest-responsive host compounds which allow rapid guest screening

Novel chromogenic, guest-sensitive host compounds

Structural comparisons between methylated and unmethylated nitrophenyl lophines

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