Chromotropism of imidazole derivatives. Part 1. 4,5-Bis-(4-methoxyphenyl)-2-(4-nitrophenyl)imidazolium acetate dihydrate

Sakaino, Yoshiko; Takizawa, Toshiharu; Inouye, Yoshinobu; Kakisawa, Hiroshi

doi:10.1039/p29860001623

Cited by 18 publications

(7 citation statements)

References 2 publications

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“…The dimers dissociate to the radicals upon irradiation, heating, and trituration. Similar properties have been obtained in crystals of 4,5-bis-(4-methoxyphenyl)-2-(4-nitrophenyl) imidazolium acetate dihydrate that show rapid color change upon drying, trituration, or heating. , 4,5-Bis(methoxyphenyl)-2-(4-nitrophenyl)-1 H -imidazole and 4,5-bis(methoxyphenyl)-2-(3-nitrophenyl)-1 H -imidazole form, with different guest molecules, a wide variety of inclusion compounds of different colors, changing from yellow to black. Kaftory et al described the thermochromic properties, crystal structure, and thermal behavior of inclusion compounds of 4,5-diphenyl-2-(4-nitrophenyl)-1 H -imidazole and 4,5-diphenyl-2-(2-hydroxy-5-nitrophenyl)-1 H -imidazole.…”

Section: Introductionsupporting

confidence: 61%

Chromotropic Behavior of Lophine Nitro-Derivatives

Fridman

Speiser

Kaftory

2006

Crystal Growth & Design

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The crystal and molecular structures of two novel derivatives of the lophine chromophore with different solvents of crystallization are presented and discussed. Phenol, 2-[4,5-bis(4-methoxyphenyl)-1H-imidazole-2-yl]-4-nitro (1) and phenol, 2-[4,5bis(4-methyl-phenyl)-1H-imidazole-2-yl]-4-nitro (2) form inclusion compounds with various guest molecules. The guest molecules interconnect host molecules of 1 and 2 through hydrogen bonds. The inclusion compounds showed chromotropic properties upon trituration, heating, or using different solvents for crystallization. The thermochromic properties have been determined by the removal of the guest molecules. To clarify the relations between the color, thermochromic properties, and the role of host in crystal packing, we have determined and compared a single-crystal X-ray analysis of six crystal structures of the two compounds. Thermal behavior in the solid state and spectroscopic behavior at different pH values and at various solvents are presented and discussed.

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Section: Introductionsupporting

confidence: 61%

Chromotropic Behavior of Lophine Nitro-Derivatives

Fridman

Speiser

Kaftory

2006

Crystal Growth & Design

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“…Dynamic materials, capable of responding to their environment, are currently receiving a great deal of attention. Such systems require flexibility which may be achieved using weak interactions such as hydrogen bonding 1,2 or through the use of suitable metals and ligands in coordination compounds. [3][4][5] Metalorganic frameworks (MOFs) are examples of the latter, and are of particular interest for their potential use as storage devices or as sensors.…”

Section: Introductionmentioning

confidence: 99%

A new class of thermo- and solvatochromic metal–organic frameworks based on 4-(pyridin-4-yl)benzoic acid

2012

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Using 4-(pyridin-4-yl)benzoic acid, 44pba (1) as a ligand, two new metal-coordination networks [Co(4)(44pba)(8)](n)·[(DMF)(3)·(EtOH)(0.25)·(H(2)O)(4)](n) (2) and [Ni(4)(44pba)(8)](n)·[(DMF)(3.5)·(EtOH)·(H(2)O)(1.5)](n) (3) were synthesized by solvothermal methods and structurally characterized. Compounds 2 and 3 are isostructural but differ in their solvent content. Each is a 2D-network which forms a spiral parallel to [001], giving rise to three distinct large channels, accounting for some 47% of the unit cell volume. Both 2 and 3 display water-induced phase transformations with chromotropism, which has been confirmed by TGA and XRPD analysis. Solvatochromism in 2 is also evident with crystals exhibiting a range of colours depending on the solvent included. This phenomenon has been characterized using TGA, XRPD and UV-vis spectrophotometry.

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“…Such a process was also observed by heating bis-(4-methoxyphenyl)-2-(4-nitrophenyl)-1H-imidazolium acetate dihydrate. 2 The second endotherm at 241 ЊC (∆H = 99.6 kJ mol Ϫ1 ) is assigned to the melting of the imidazole-picric acid compound. The thermal behavior is under study.…”

Section: Resultsmentioning

confidence: 99%

Crystal structure and thermochromic behavior of the inclusion compounds of 4,5-diphenyl-2-(4-nitrophenyl)-1H-imidazole and of 4,5-diphenyl-2-(2-hydroxy-5-nitrophenyl)-1H-imidazole

Kaftory¹,

Taycher²,

Botoshansky³

1998

J. Chem. Soc., Perkin Trans. 2

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4,5-Diphenyl-2-(4-nitrophenyl)-1H-imidazole 2 and 4,5-diphenyl-2-(2-hydroxy-5-nitrophenyl)-1Himidazole 3 form inclusion compounds with various guest molecules that possess hydrogen donor or hydrogen acceptor groups. The guest molecules play a crucial role in building up the three-dimensional structure. The guest molecules link host molecules through hydrogen bonds. The colors of the solid compounds vary from light yellow to dark red. The thermochromic properties have been determined by the removal of the guest molecules. The crystal structure and the thermal behavior are described and discussed.

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Chromotropism of imidazole derivatives. Part 1. 4,5-Bis-(4-methoxyphenyl)-2-(4-nitrophenyl)imidazolium acetate dihydrate

Cited by 18 publications

References 2 publications

Chromotropic Behavior of Lophine Nitro-Derivatives

Chromotropic Behavior of Lophine Nitro-Derivatives

A new class of thermo- and solvatochromic metal–organic frameworks based on 4-(pyridin-4-yl)benzoic acid

Crystal structure and thermochromic behavior of the inclusion compounds of 4,5-diphenyl-2-(4-nitrophenyl)-1H-imidazole and of 4,5-diphenyl-2-(2-hydroxy-5-nitrophenyl)-1H-imidazole

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