Imidazole derivatives: A comprehensive survey of their recognition properties

Molina, Pedro; Tárraga, Alberto; Otón, Francisco

doi:10.1039/c2ob06808g

Cited by 210 publications

(145 citation statements)

References 93 publications

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“…35 This feature of the imidazole ring has been utilized in crystal engineering and supramolecular chemistry. 36 Furthermore, the nitrogen atoms of imidazole possess high PT ability which plays a vital role in biological systems such as cytochrome c. 37 We have synthesized TTF derivatives substituted with imidazole rings (6, Chart 2), and investigated the effects of H-bonds on the crystal structures and physical properties of the CT complexes.…”

Section: Diamino-dibenzo Ttfmentioning

confidence: 99%

Cooperation of Hydrogen-Bond and Charge-Transfer Interactions in Molecular Complexes in the Solid State

Morita

Murata

Nakasuji

2013

Bulletin of the Chemical Society of Japan

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Our recent studies for the development of conducting charge-transfer complexes with well-defined assembled structures based on the cooperation of hydrogen-bond and charge-transfer interactions are described. We have designed and synthesized hydrogen-bonded charge-transfer complexes based on (1) tetrathiafulvalene derivatives having nucleobases, aminobenzo and imidazole moieties, and (2) tetracyanoquinodimethane radical anion salts with hydrogen-bondfunctionalized phenalenyl and protonated oligo(imidazole) cations. The directional and site-selective hydrogen-bonds formed various supramolecular network structures, constructing segregated columns as the conduction path. Furthermore, the high polarity of hydrogen-bonds caused strong donoracceptor or cationanion electrostatic interactions modulating the ionicity of component molecules and the electronic structure of conduction columns. Such electronic modulation effects in addition to controlling the molecular arrangement realized the first purely organic molecular metal based on a hydrogenbonded charge-transfer complex in the p-chloranil complex of an imidazole-functionalized tetrathiafulvalene derivative. The proton-donating/accepting ability of the hydrogen-bonding sites afforded the simultaneous proton-and charge-transfer complexes, demonstrating an important prompt for the realization of cooperative protonelectron-transfer systems.

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Section: Diamino-dibenzo Ttfmentioning

confidence: 99%

Cooperation of Hydrogen-Bond and Charge-Transfer Interactions in Molecular Complexes in the Solid State

Morita

Murata

Nakasuji

2013

Bulletin of the Chemical Society of Japan

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“…Imidazole is an aromatic ring having two nitrogen atoms as the H-bonding sites and constructs diverse supramolecular architectures. 8 The self-assembling ability of imidazole has been also utilized in the development of electronic materials such as organic conductors 9 and molecular magnets. 10 Imidazole also behaves as a Brønsted acid and base and generates protonated cation and deprotonated anion species.…”

mentioning

confidence: 99%

Syntheses, Redox Properties, Self-Assembled Structures, and Charge-Transfer Complexes of Imidazole- and Benzimidazole-Annelated Tetrathiafulvalene Derivatives

Murata

Yamamoto

Yakiyama

et al. 2013

Bulletin of the Chemical Society of Japan

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New tetrathiafulvalene (TTF)-type electron-donor molecules annelated with imidazole or benzimidazole moiety were designed and synthesized by the phosphite-mediated coupling reactions of imidazole-or benzimidazole-annelated 1,3-dithiole-2-thiones. The effect of imidazole-annelation on the redox properties was evaluated by theoretical calculation and electrochemical measurement, and the imidazole-annelation slightly enhances the electron-donating abilities of parent TTF and benzo-TTF skeletons. The substitution of the imidazole ring with an electron-withdrawing cyano group caused a large high potential shift of the oxidation potentials in the cyclic voltammetry and an intense intramolecular chargetransfer absorption band in the electronic spectrum. The self-assembling ability was investigated by crystal structure analysis, where solvent or counter anion mediated one-dimensional hydrogen-bonded arrays of imidazole rings were linked through ³-stacks and S£S interactions to construct multidimensional networks. The donor molecules afforded weak charge-transfer complexes with tetracyanoquinodimethane (TCNQ) and fully ionic complexes with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) and 2,3,5,6-tetrafluoro-TCNQ. In the crystal structures of TCNQ complex and iodine salt of a benzimidazole-annelated derivative, ³-stacking motifs, donoracceptor alternating stack, and ³-stacking dimer, respectively, were interacted through hydrogen-bonds.Tetrathiafulvalene (TTF) is a strong ³-donor molecule and has been widely utilized in the development of various molecule-based electronic materials.1 The most attractive and noticeable properties of the TTF system is the electrical conduction in charge-transfer (CT) complexes and salts, and vigorous materials exploration based on the TTF system have produced intriguing phenomena and functions.2 To achieve CT complexes and salts showing desired properties, the control of relative molecular orientation with the aid of intermolecular interactions is necessary.3,4 Hydrogen-bonding (H-bond) is a robust and highly directional intermolecular interaction and has been introduced into CT complexes and salts for the establishment of conduction paths and for the increase of electronic and structural dimensionalities. 3,5,6 Furthermore, the cooperation of proton-transfer (PT) at the H-bonding sites with electrontransfer of the redox-active sites is expected to provide a new strategy for materials exploration.

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“…Imidazole is a widely used functional group in anion detecting sensor systems because it is able to behave as an excellent hydrogen-bonding donor moiety, and the acidity of the NH group can be easily tuned by adjusting the electronic properties of neighboring substituents so that it can recognize anion through hydrogen-bonding and deprotonation interaction [13][14][15][16]. Currently, the interesting non-covalent binding motif between electron-deficient aromatic ring and anion, namely anion-p interaction, is generating much interest in theoretical and experimental investigations because anion-p or anion-proton interactions play a crucial role in many chemical and biological processes, and could have potential application in medicine and in the environment [17][18][19].…”

Section: Introductionmentioning

confidence: 99%

A novel colorimetric and fluorescent sensor for fluoride detection based on a three-arm phenanthroline derivative

Yang

Cui

et al. 2014

J Mater Sci

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A novel highly sensitive colorimetric receptor trisphen for F -ion based on three-arm phenthroline derevative trisphen had been successfully designed, synthesized, and characterized. Experiments showed that receptor trisphen could selectively recognize the F -and AcO -in DMSO and even in competitive hydrogen-bonding mixture solutions. The ability of recognition and the bond between trisphen and anions were determined using naked eye, UVvis, and fluorescence analyses. Benesi-Hildebrand equation indicated that receptor trisphen associated with F -and AcO -in a 1:2 stoichiometry. Moreover, 1 H NMR experiments were carried out to explore the insight of interaction between trishen and anions. To the best of our knowledge, this is the first example of anion sensor based on three-arm phenanthroline derivative.

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Imidazole derivatives: A comprehensive survey of their recognition properties

Cited by 210 publications

References 93 publications

Cooperation of Hydrogen-Bond and Charge-Transfer Interactions in Molecular Complexes in the Solid State

Cooperation of Hydrogen-Bond and Charge-Transfer Interactions in Molecular Complexes in the Solid State

Syntheses, Redox Properties, Self-Assembled Structures, and Charge-Transfer Complexes of Imidazole- and Benzimidazole-Annelated Tetrathiafulvalene Derivatives

A novel colorimetric and fluorescent sensor for fluoride detection based on a three-arm phenanthroline derivative

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