Thioamide, urea and thiourea bridged rhenium(I) complexes as luminescent anion receptors

Odago, Maurice O.; Hoffman, Amanda E.; Carpenter, R. L.; Tse, Douglas Chi Tak; Sun, Shih‐Sheng; Lees, Alistair J.

doi:10.1016/j.ica.2011.02.065

Cited by 21 publications

(8 citation statements)

References 19 publications

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“…The aromatic proton peaks for the compound resonated in the region from 7. [31][32][33] Moreover, evidence of a successful reaction was also confirmed by the presence of additional absorption bands at 1681 cm −1 for the pyridyl group (CvN) and 1604 cm −1 for the amide carbonyl group (CvO), respectively.…”

Section: Synthesis and Characterisation Of Ligand L1mentioning

confidence: 99%

Selective Cu and Ni-MOFs as pre-catalysts for the hydrogenation of furfural to furfuryl alcohol

et al. 2023

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Section: Synthesis and Characterisation Of Ligand L1mentioning

confidence: 99%

Selective Cu and Ni-MOFs as pre-catalysts for the hydrogenation of furfural to furfuryl alcohol

et al. 2023

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“…The structural chemistry of potentially useful organic ligands for applications in a range of scientific areas, such as coordination chemistry, bioinorganic, medicinal chemistry and drug development, continues unabated [1][2][3][4]. At the heart of the many and varied classes of organic ligands lies the benzamide/carboxamide group of compounds and their derivatives such as isophthalamides [5][6][7]. These and closely related compounds have been developed over the past two decades and especially in the drive to acquire a deeper and more fundamental knowledge in foldamer chemistry and host•guest science [8][9][10].…”

Section: Introductionmentioning

confidence: 99%

Roles of Hydrogen, Halogen Bonding and Aromatic Stacking in a Series of Isophthalamides

et al. 2023

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The synthesis and spectroscopic characterisation of six bis(5-X-pyridine-2-yl)isophthalamides (X = H, F, Br, Cl, I, NO2) are reported, together with five crystal structure analyses (for X = H, F to I). The isophthalamides span a range of conformations as syn/anti (H-DIP; I-DIP), anti/anti- (F-DIP; Br-DIP) and with both present in ratio 2:1 in Cl-DIP. The essentially isostructural F-DIP and Br-DIP molecules (using strong amide…amide interactions) aggregate into 2D molecular sheets that align with either F/H or Br atoms at the sheet surfaces (interfaces), respectively. Sheets are linked by weak C-H⋯F contacts in F-DIP and by Br⋯Br halogen bonding interactions as a ‘wall of bromines’ at the Br atom rich interfaces in Br-DIP. Cl-DIP is an unusual crystal structure incorporating both syn/anti and anti/anti molecular conformations in the asymmetric unit (Z’ = 3). The I-DIP•½(H2O) hemihydrate structure has a water molecule residing on a twofold axis between two I-DIPs and has hydrogen and N⋯I (Nc = 0.88) halogen bonding. The hydrate is central to an unusual synthon and involved in six hydrogen bonding interactions/contacts. Contact enrichment analysis on the Hirshfeld surface demonstrates that F-DIP, Cl-DIP and Br-DIP have especially over-represented halogen···halogen interactions. With the F-DIP, Cl-DIP and Br-DIP molecules having an elongated skeleton, the formation of layers of halogen atoms in planes perpendicular to the long unit cell axis occurs in the crystal packings. All six DIPs were analysed by ab initio calculations and conformational analysis; comparisons are made between their minimized structures and the five crystal structures. In addition, physicochemical properties are compared and assessed.

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“…A variety of organic scaffolds and functional groups containing hydrogen-bond donors have been utilized for anion recognition, such as hydrazones, amides, , sulfonamides, , thioamides, pyrroles, imidazolium cations, ureas, thioureas, and guanidinium and amidinium cations. , For weakly coordinating nitrate anions with large hydration shells, however, even these hydrogen-bond donors alone are sometimes not sufficient for effective binding of nitrate anions, especially in a solution medium. , Thus, a combination of electrostatic and hydrogen-bonding interactions imparted on the receptor moiety would be an appropriate choice for the selective recognition of weakly coordinating nitrate anions.…”

Section: Introductionmentioning

confidence: 99%

Recognition, Encapsulation, and Selective Fluorescence Sensing of Nitrate Anion by Neutral C₃-Symmetric Tripodal Podands Bearing Amide Functionality

Singh

Sun

2012

J. Org. Chem.

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A series of neutral C(3)-symmetric acyclic artificial receptors incorporating amide functionality has been designed, synthesized, and fully characterized. Upon protonation, these conformationally flexible N-bridged tripodal podands 1-5 form in situ cone shape conformation through hydrogen bonding and C-H···π interactions. The protonation-induced interior preorganized cavity is capable of entrapping nitrate anions through the amide N-H bonds to form discrete nitrate complexes (1a-5a), which were fully characterized by NMR, HRESI mass spectra, and single crystal structures. By incorporating suitable fluorophores at each branch of the tripod receptor, the resulting fluorescent receptor 5 selectively recognized nitrate anions by fluorescent quenching in a DMSO solution and displayed one of the highest binding affinities for nitrate anions reported so far in polar media. Receptor 5 represents a unique example of a neutral receptor for the recognition of nitrate anions in polar solvent media by its zwitterionic form. The possible mechanism of proton-induced preorganization of these flexible, acyclic receptors in a convergent cone conformation followed by nitrate complexation has been proposed to rationalize the effective nitrate recognition.

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Thioamide, urea and thiourea bridged rhenium(I) complexes as luminescent anion receptors

Cited by 21 publications

References 19 publications

Selective Cu and Ni-MOFs as pre-catalysts for the hydrogenation of furfural to furfuryl alcohol

Selective Cu and Ni-MOFs as pre-catalysts for the hydrogenation of furfural to furfuryl alcohol

Roles of Hydrogen, Halogen Bonding and Aromatic Stacking in a Series of Isophthalamides

Recognition, Encapsulation, and Selective Fluorescence Sensing of Nitrate Anion by Neutral C₃-Symmetric Tripodal Podands Bearing Amide Functionality

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Thioamide, urea and thiourea bridged rhenium(I) complexes as luminescent anion receptors

Cited by 21 publications

References 19 publications

Selective Cu and Ni-MOFs as pre-catalysts for the hydrogenation of furfural to furfuryl alcohol

Selective Cu and Ni-MOFs as pre-catalysts for the hydrogenation of furfural to furfuryl alcohol

Roles of Hydrogen, Halogen Bonding and Aromatic Stacking in a Series of Isophthalamides

Recognition, Encapsulation, and Selective Fluorescence Sensing of Nitrate Anion by Neutral C3-Symmetric Tripodal Podands Bearing Amide Functionality

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Product

Resources

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Recognition, Encapsulation, and Selective Fluorescence Sensing of Nitrate Anion by Neutral C₃-Symmetric Tripodal Podands Bearing Amide Functionality