Progressive Cation Triggered Anion Binding by Electron-Rich Scaffold: Case Study of a Neutral Tripodal Naphthyl Thiourea Receptor

Manna, Utsab; Das, Gopal

doi:10.1021/acs.cgd.8b00259

Cited by 11 publications

(4 citation statements)

References 74 publications

(147 reference statements)

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“…Continuing our group’s pursuit in the field of substituent driven anionic/hydrated anionic supramolecular self-assemblies of acyclic receptors, − herein we develop a class of nitro-phenyl functionalized comparatively less cooperative and more challenging positional isomeric linear bis-urea receptors L 1 – L 3 (Scheme ), derived from the least converging aromatic diamine ( para -phenylenediamine) to investigate the coordination behavior with anions/hydrated anions in neutral form. Structural studies reveal that both para -isomer ( L 1 ) and meta -isomer ( L 1 ) are capable of (HCO 3 ) 2 -dimer entrapment either by fluoride or hydroxide induced fixation of atmospheric CO 2 in complexes 1a , 2a , and 2b .…”

Section: Introductionmentioning

confidence: 99%

Self-Assemblies of Positional Isomeric Linear Bis-Urea Ligands with Oxyanions/Hydrated Oxyanions: Evidence of F^– and OH^– Induced Atmospheric CO₂ Fixation

Manna

Das

2018

Crystal Growth & Design

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A set of three positional isomeric nitro-phenyl functionalized linear bis-urea scaffolds has been purposefully synthesized from p-phenylenediamine, basically for investigating the extensive anion-coordination behavior in their neutral form. The para-isomer (L 1 ) and meta-isomer (L 2 ) can readily form bicarbonate dimer (HCO3)2 entrapped neutral self-assemblies in the solid state by either fluoride or hydroxide induced atmospheric CO2 fixation. In the bulk scale and based on the isolated yield of (HCO3)2 entrapped complexes of L 1 and L 2 , it has been found that 6.7, 7.3, and 6.2 mmol of CO2 can be fixed respectively by 1 mmol of linear bis-urea derivatives. The other planar acetate anions in their bare and hydrated form [(OCOCH3)2(H2O)] are coordinated by hydrogen-bonding interactions in noncooperative fashion with L 1 and L 2 respectively. Interestingly, the para-isomer L 1 entraps bisulfate dimer (HSO4)2, while the meta-isomer L 2 has been found to self-assemble with divalent sulfate (SO4 2–) and polymeric dihydrogen-phosphate (H2PO4) n by noncooperative hydrogen-bonding interactions also. However, successful crystallization of any anion complexes with ortho-isomer (L 3 ) was not fruitful; instead the free L 3 ligand structure has been attained in most of the cases. This phenomena occurs owing to the steric hindrance provided by the nitro group at the ortho-position, which probably hampers the facile inclusion via coordination of an anion due to electrostatic factors, as observed and confirmed by the presence of intramolecular hydrogen-bonding interactions in the crystal structures of free ligand L 3 .

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Section: Introductionmentioning

confidence: 99%

Self-Assemblies of Positional Isomeric Linear Bis-Urea Ligands with Oxyanions/Hydrated Oxyanions: Evidence of F^– and OH^– Induced Atmospheric CO₂ Fixation

Manna

Das

2018

Crystal Growth & Design

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“…Bisulfates also are known to affect human health by causing breathing difficulties, burning pain in the mouth, chest pain, burning of the esophagus, diarrhea, etc. To date, various neutral and protonated anion receptors, having multiple NH units, have been reported with topological complementarities in their molecular assemblies. − In this regard, tactically synthesized urea-derived polytopic neutral receptors seem to be potentially significant to researchers for the complete encapsulation or trapping of monomeric, dimeric, or polymeric oxyanions. In the area of supramolecular chemistry, of late, the roles of hydrogen bonds (HBs), which facilitate favorable hydrogen bonds between anions, have gained much attention.…”

Section: Introductionmentioning

confidence: 99%

Trapped Cyclic Dimeric Oxyanion Assembly by a Urea-Functionalized Receptor: Potent Application in Linear Discriminant Analysis and as Antibacterial Agents

Das

Roy

Konwar

et al. 2022

Crystal Growth & Design

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The naphthalimide-based linear monourea receptors L 1 and L 2 exhibit anion (oxyanions and halides) binding in the solid and solution states. The receptor L 1 could render fluoride-/hydroxide-induced aerial CO2 fixation efficiently, leading to air-stable assembling of dianions enclosed by n-TBA cations via the formation of an R2 2(8)-type cylindrical dimeric arrangement. The assembly of the anions is stabilized via short-range hydrogen-bonding interactions. A cyclic dimeric assembly of bisulfate anions sealed by the linear tetrameric assembly of the host molecule was also evidenced from the solid-state architecture. Upon addition of excess amounts of chloride and bromide anion, linearly assembled L 1 captured a cyclic chloride–water and bromide–water tetrameric cluster. The ligands were capable of discriminating five relevant anions with 100% classification accuracy in aqueous media on the basis of multivariate pattern analysis. Interestingly, the ligands L 1 and L 2 displayed notable bactericidal activity against the Gram-negative pathogen E. coli MTCC 433 and were nontoxic to cultured human embryonic kidney (HEK 293) cells.

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“…In this paper we consider the interplay among hydrogen bonding, chirality, molecular flexibility, and crystal packing using functionalized thioureas as an example. Hydrogen bonding in thioureas plays an important role in their crystal packing and various applications such as sensors, catalysts, membrane transporters, and anion receptors. , In spite of a plethora of studies on hydrogen bonding and its role in thioureas, little is known about compounds containing the thiourea fragment bonded to the phosphoryl group; only 15 entries have been deposited in the CSD.…”

Section: Introductionmentioning

confidence: 99%

Competitive Hydrogen Bonding and Unprecedented Polymorphism in Selected Chiral Phosphorylated Thioureas

Ivshin

Metlushka

Zinnatullin

et al. 2021

Crystal Growth & Design

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New racemic and enantiopure N-phosphorylated thioureas bearing 1phenylethyl or tetrahydronaphthalenyl fragments were synthesized. According to NMR data assisted by DFT calculations, the preferred conformation is stabilized by an intramolecular hydrogen bond. This form in solution is in equilibrium with dimeric N− H•••S hydrogen-bonded associates, the population depending on the concentration. In the crystalline phase the low-energy conformation with an intramolecular H-bond is realized only in the racemic tetrahydronaphthalenyl derivative. In most crystals various types of intermolecular hydrogen bonding are observed, accompanied by the formation of infinite linear chains or helical structures. Due to the conformational lability of compounds and competitive intermolecular H-bonding, multiple polymorphic modifications are formed. Therefore, crystallization of enantiopure 1-phenylethyl derivatives from various solvents results in concomitant polymorphs at room temperature. One of them undergoes reversible two-step phase transitions from the high-symmetry I4 1 space group (Z′ = 1, no disorder) via the P4 1 space group (Z′ = 6) to the monoclinic P2 1 space group (Z′ = 16) accompanied by drastic concerted conformational changes. Notably, the optimization of the crystal packing is observed upon phase transitions with a gradual reduction of the void space in the unit cell from 4.5% to 0.8%. This is a rare case of several high-Z′ polymorphs for one compound, with chirality playing an important role.

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Progressive Cation Triggered Anion Binding by Electron-Rich Scaffold: Case Study of a Neutral Tripodal Naphthyl Thiourea Receptor

Cited by 11 publications

References 74 publications

Self-Assemblies of Positional Isomeric Linear Bis-Urea Ligands with Oxyanions/Hydrated Oxyanions: Evidence of F^– and OH^– Induced Atmospheric CO₂ Fixation

Self-Assemblies of Positional Isomeric Linear Bis-Urea Ligands with Oxyanions/Hydrated Oxyanions: Evidence of F^– and OH^– Induced Atmospheric CO₂ Fixation

Trapped Cyclic Dimeric Oxyanion Assembly by a Urea-Functionalized Receptor: Potent Application in Linear Discriminant Analysis and as Antibacterial Agents

Competitive Hydrogen Bonding and Unprecedented Polymorphism in Selected Chiral Phosphorylated Thioureas

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Progressive Cation Triggered Anion Binding by Electron-Rich Scaffold: Case Study of a Neutral Tripodal Naphthyl Thiourea Receptor

Cited by 11 publications

References 74 publications

Self-Assemblies of Positional Isomeric Linear Bis-Urea Ligands with Oxyanions/Hydrated Oxyanions: Evidence of F– and OH– Induced Atmospheric CO2 Fixation

Self-Assemblies of Positional Isomeric Linear Bis-Urea Ligands with Oxyanions/Hydrated Oxyanions: Evidence of F– and OH– Induced Atmospheric CO2 Fixation

Trapped Cyclic Dimeric Oxyanion Assembly by a Urea-Functionalized Receptor: Potent Application in Linear Discriminant Analysis and as Antibacterial Agents

Competitive Hydrogen Bonding and Unprecedented Polymorphism in Selected Chiral Phosphorylated Thioureas

Contact Info

Product

Resources

About

Self-Assemblies of Positional Isomeric Linear Bis-Urea Ligands with Oxyanions/Hydrated Oxyanions: Evidence of F^– and OH^– Induced Atmospheric CO₂ Fixation

Self-Assemblies of Positional Isomeric Linear Bis-Urea Ligands with Oxyanions/Hydrated Oxyanions: Evidence of F^– and OH^– Induced Atmospheric CO₂ Fixation