Design and synthesis of preorganized tripodal fluororeceptors based on hydrogen bonding of thiourea groups for optical phosphate ion sensing

Sasaki, Shin Ichi; Citterio, Daniel; Ozawa, Satoru; Suzuki, Kôji

doi:10.1039/b105913k

Cited by 98 publications

(41 citation statements)

References 22 publications

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“…[40][41][42] A range of tripodal trisureas that bind dihydrogenphosphate and acetate anions have also been reported. [43] Thioureas in particular are relatively acidic, which leads to strong hydrogen-bonding interactions (although the stabilisation of the conjugate base can lead to deprotonation by basic anions [44][45][46][47] ). The thiourea sulfur atom is more exposed than the urea carbonyl oxygen atom, however, and thus urea self-association can compete with hydrogen bonding to a target anion guest, in some cases leading to species such as gels.…”

Section: Introductionmentioning

confidence: 99%

Enhanced Anion Binding from Unusual Coordination Modes of Bis(thiourea) Ligands in Platinum Group Metal Complexes

Soriano¹,

Lenthall²,

Anderson³

et al. 2010

Chemistry A European J

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Treatment of a range of bis(thiourea) ligands with inert organometallic transition-metal ions gives a number of novel complexes that exhibit unusual ligand binding modes and significantly enhanced anion binding ability. The ruthenium(II) complex [Ru(η(6)-p-cymene)(κS,S',N-L(3)-H)](+) (2b) possesses juxtaposed four- and seven-membered chelate rings and binds anions as both 1:1 and 2:1 host guest complexes. The pyridyl bis(thiourea) complex [Ru(η(6)-p-cymeme)(κS,S',N(py)-L(4))](2+) (4) binds anions in both 1:1 and 1:2 species, whereas the free ligand is ineffective because of intramolecular NH⋅⋅⋅N hydrogen bonding. Novel palladium(II) complexes with nine- and ten-membered chelate rings are also reported.

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Section: Introductionmentioning

confidence: 99%

Enhanced Anion Binding from Unusual Coordination Modes of Bis(thiourea) Ligands in Platinum Group Metal Complexes

Soriano¹,

Lenthall²,

Anderson³

et al. 2010

Chemistry A European J

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“…For example, high stability constants of (thio)urea derivatives bearing a variety of substituents with hydrophilic anions, such as H2PO4 -, have been previously reported. [51][52][53][54] Their hydrogen-bonding abilities can also afford their use as organic gelators. [46][47][48][49] A phenylurea-modified tip (PhUET-tip) was used to measure the adhesion force on the COOH-terminated SAM (MHA-SAM) surface.…”

Section: Hydrogen Bonding Force Between Phenylurea and Carboxyl Groupmentioning

confidence: 99%

“…Recently, the hydrogenbonding ability of (thio)urea compounds has received considerable attention, and has been utilized to develop highly functionalized novel materials, such as organic gelators, [46][47][48][49] and synthetic receptors for hydrophilic anions, 50 including H2PO4 -, [51][52][53][54] halide, [55][56][57][58][59][60] and ATP. 61 It has been reported that the silica nanosphere catalyst, functionalized with a urea derivative (i.e., ureidopropyl group), can activate the carbonyl compound, a reaction substrate for its catalytic reactions, based on the urea's hydrogen-bonding ability.…”

Section: Introductionmentioning

confidence: 99%

Effect of Intramonolayer Hydrogen Bonding of Carboxyl Groups in Self-assembled Monolayers on a Single Force with Phenylurea on an AFM Probe Tip

2006

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IntroductionDuring the recent decade, atomic force microscopy (AFM) has attracted much attention as a promising analytical tool for precisely measuring intermolecular forces.1-5 AFM can be used to detect the force between its probe tip and substrate surfaces, even at the pN level. It is thus of great importance that there is almost no limitation of the environment and conditions where the AFM force measurements are carried out. Thus, if the AFM probe tip and the substrate are modified chemically with selfassembled monolayers (SAMs) 6,7 terminating with target functional groups, the intermolecular force in their molecular pairs can be evaluated by force-curve measurements in appropriate solvents by AFM. [8][9][10][11][12][13][14][15][16][17][18][19]36 Furthermore, the individual force for a variety of intermolecular forces at a single-molecule level can also be evaluated by statistical analyses of the forces obtained by repetitive adhesion force measurements. [20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35]37,38 In our previous studies, we measured specific intermolecular forces attributable to the characteristic molecular functionalities of the functional molecules, such as crown ether 36,37 and spirobenzopyran 38 derivatives, attached covalently on the probe tips. These functionalized AFM probe tips, which possess a powerful capability of detecting supramolecular interactions, can be potentially utilized for developing a novel analytical tool for surface analysis based on force sensing by AFM.In such AFM force measurements, SAMs are often used for conveniently established covalent bonding of the target molecules onto the surfaces of the tip and substrate. Then, the intramonolayer interaction between the components in the SAMs can be expected to affect the force observed by the AFM technique. In other words, the AFM technique could detect such effects as the intramonolayer interaction on the interaction between the tip and the substrate. Intramonolayer hydrogen bonding is crucial in the SAMs of thiols or silanes bearing a terminal functional group, which can form hydrogen bondings between themselves. For example, terminal carboxyl groups in the SAMs of ω-carboxyalkanethiol can easily form hydrogen bonding within the monolayers. 39-42The COOH-terminated SAMs, such as thiol and silane, have been analyzed by FT-IR spectroscopy. 44 Especially, in the case of COOH-terminated SAMs, the effect of the intramonolayer hydrogen bonding between the neighboring carboxyl groups in the SAMs had been considered with respect to their surface property, such as wettability 45 and surface acidity (pKa) of the carboxyl groups. [41][42][43] In the present paper, we report an AFM force spectroscopic study concerning the effect of intramonolayer hydrogen bonding in COOH-terminated SAMs of 6-mercaptohexanoic acid (MHA) on the adhesion force observed between a SAM of MHA and a phenylurea derivative attached to the substrate and probe tip, respectively.Urea derivatives have a powerful ability to form hydrogen bondings, sin...

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“…To date the pyrene Excimer/monomer system has been exploited mainly for cation sensing [59][60][61][62][63][64][65][66][67][68][69][70] and increasingly for anion sensing [71][72][73][74] . To the best of our knowledge there are few examples where pyrene and (thio)urea systems have been proximally combined in anion host compounds and none based on a calixarene platform 75,76 .…”

mentioning

confidence: 99%

Chloride Selective Calix[4]arene Optical Sensor Combining Urea Functionality with Pyrene Excimer Transduction

2006

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Design and synthesis of preorganized tripodal fluororeceptors based on hydrogen bonding of thiourea groups for optical phosphate ion sensing

Cited by 98 publications

References 22 publications

Enhanced Anion Binding from Unusual Coordination Modes of Bis(thiourea) Ligands in Platinum Group Metal Complexes

Enhanced Anion Binding from Unusual Coordination Modes of Bis(thiourea) Ligands in Platinum Group Metal Complexes

Effect of Intramonolayer Hydrogen Bonding of Carboxyl Groups in Self-assembled Monolayers on a Single Force with Phenylurea on an AFM Probe Tip

Chloride Selective Calix[4]arene Optical Sensor Combining Urea Functionality with Pyrene Excimer Transduction

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