(cis)-5,10,15,20-Tetrakis[2-(arylurea)phenyl]porphyrins: novel neutral ligands for remarkably selective and exceptionally strong chloride anion complexation in (CD3)2SO

Jagessar, R. C.; Burns, Dennis H.

doi:10.1039/a702389h

Cited by 50 publications

(41 citation statements)

References 15 publications

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“…Results from our previous work suggested that the best way to bind the phosphate anion would be with two functional groups, such as neutral urea groups or charged ammonium groups (Burns et al, 2005;Calderon-Kawasaki et al, 2007;Jagessar et al, 1997Jagessar et al, , 1998, and modeling suggested the use of two more hydrogen-bonding groups to bind to the hydroxyl groups. Based on these requirements, the scaffold chosen was bis-phenol, (I) (shown in Fig.…”

Section: Commentmentioning

confidence: 99%

Two similar dibenzo cyclic ethers with dissimilar conformations

et al. 2008

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Two dibenzo cyclic ether compounds, 6,12-dibromodibenzo[d,i]-1,2,3,6,7,8-hexahydro-1,3-dioxecin (systematic name: 8,16-dibromo-2,4-dioxatricyclo[12.4.0.0(5,10)]octadeca-5,7,9,14,16,18-hexaene), C(16)H(14)Br(2)O(2), (II), and 8,14-dibromodibenzo[f,k]-1,5-dioxa-1,2,3,4,5,8,9,10-octahydrocyclododecene (systematic name: 7,19-dibromo-11,15-dioxatricyclo[14.4.0.0(5,10)]icosa-5,7,9,16,18,20-hexaene), C(18)H(18)Br(2)O(2), (III), were prepared as scaffolding for phosphate-anion receptors. In both compounds, the two aromatic rings are linked by three methylene units ortho to the oxygen substituent of each ring. The only difference between the two compounds is the number of methylene units linking the two ether O atoms. The dibenzo cyclic ether with an ether linkage of one methylene unit adopts a chair-like conformation, where the two aromatic rings are parallel to each other. On the other hand, the dibenzo cyclic ether with an oxygen linkage of three methylene units adopts a bowl-like conformation. The latter scaffold configuration is the only structure of the two that would allow for the placement of convergent functional groups necessary for the establishment of an anion-selective binding pocket.

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Section: Commentmentioning

confidence: 99%

Two similar dibenzo cyclic ethers with dissimilar conformations

et al. 2008

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“…Also, neutral anion receptors, especially those of the amido type exploit hydrogen bonding interactions with anions and are found in biological systems. Depending on their spatial orientation (geometry), neutral amides are expected to selectively complex guest substrates 12-14,20-24. There are several reports of anion recognition by urea receptors [15][16][17][18][19][25][26][27] . For example, A bis-urea and a bis-thiourea host (1), both derived from 1,3-bis(aminomethyl)benzene have been shown to bind dihydrogenphosphate selectively over various other anions according to the selectivity trend:…”

Section: Introductionmentioning

confidence: 99%

“…Neutral porphyrin urea anion receptors (3)- (6) and their corresponding zinc complexes (7)(8)(9), exploiting the neutral urea binding motif and in case of the zinc complexes, Lewis acid interactions have been reported [16][17] ( Figure 2). Significantly large association constants have been reported for these compounds binding to anion in highly competitive solvents such as d 6 -DMSO.…”

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Syntheses and Characterisation of Diurea Molecular Tweesors for the Recognition of Anion

Jagessar

2013

J. Chil. Chem. Soc.

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Two novel urea anion receptors (11) and (12) were synthesized from building block 3,3' methylene diamine and was characterized via the techniques of 1 H NMR, 13 C NMR, DEPT-135 1 H-1 H COSY, HMQC and HMBC spectroscopy. The 1 H NMR profile of both compounds reveals diagnostic peaks. For compound (11), the urea NH protons resonate as two singlets downfield at 8.706 ppm and 8.635 ppm, whereas for compound (12) these two urea -NHCONH protons resonate together at 8.614 ppm. There seem to be no rotation of the structure on the NMR time scale as the bridged CH 2 protons resonate as a singlet. The integration pattern for the aromatic hydrogens for both compounds is: 2: 4: 2: 4: 4, consistent with the structure.13 CNMR spectrums reveal fourteen signals for both structures in accordance with fourteen different types of carbon. Dept-135 indicates eight different CH protons. Preliminary anion binding studies via 1 HNMR spectroscopy revealed complexation with dicarboxylate anions in the highly competitive solvent, d 6 -DMSO.

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“…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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(cis)-5,10,15,20-Tetrakis[2-(arylurea)phenyl]porphyrins: novel neutral ligands for remarkably selective and exceptionally strong chloride anion complexation in (CD3)2SO

Cited by 50 publications

References 15 publications

Two similar dibenzo cyclic ethers with dissimilar conformations

Two similar dibenzo cyclic ethers with dissimilar conformations

Syntheses and Characterisation of Diurea Molecular Tweesors for the Recognition of Anion

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

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