Influence of dimensionality and charge on anion binding in amide-based macrocyclic receptors

Kang, Sung Ok; Hossain, Md. Alamgir; Bowman‐James, Kristin

doi:10.1016/j.ccr.2006.06.006

Cited by 197 publications

(90 citation statements)

References 84 publications

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“…A noticeable increase in stability was observed in going from [30]aneN 10 (70) to the larger [33]aneN 11 (71), suggesting possible inclusion of the anion within the macrocyclic hole.…”

Section: Anionic Complexes: Supercomplex Formationmentioning

confidence: 88%

“…progression in the series led to diminished stability constants in agreement with the lower charge density of the receptors as their size is increased. However, in the case of phosphate, this was so until macrocycle [30]aneN 10 (70) was reached; for [33]aneN 11 (71), an increase in stability was observed. This was attributed to a likely inclusion of the anion in the cavity.…”

Section: Phosphate and Polyphosphate Anionsmentioning

confidence: 99%

“…The analysis of the stepwise stability constants for these systems indicated that the chief driving force in cyanometallate-polyammonium receptor binding is charge-charge interaction, which makes it difficult to modulate the selective discrimination of one guest over another. However, a representation of the constants for the equilibria [Co(CN) 6 (3−p) showed that typically the constants for a given protonation degree of the macrocycle (p) steadily decreased when going from one macrocycle to the next until [30]aneN 10 (70) was reached. From there on, an increase in stability was observed (Figure 1.40).…”

Section: Anionic Complexes: Supercomplex Formationmentioning

confidence: 99%

“…In this respect, Sessler, Ibers et al [137] were, in 1990, the first to evidence a fluoride anion residing in the central hole of a sapphyrin, a 22-π-electron pentapyrrolic expanded porphyrin (28)(29)(30)(31).…”

mentioning

confidence: 99%

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Aspects of Anion Coordination from Historical Perspectives

Bianchi¹,

Bowman‐James²,

Garc³

2011

Anion Coordination Chemistry

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“…A noticeable increase in stability was observed in going from [30]aneN 10 (70) to the larger [33]aneN 11 (71), suggesting possible inclusion of the anion within the macrocyclic hole.…”

Section: Anionic Complexes: Supercomplex Formationmentioning

confidence: 88%

Section: Phosphate and Polyphosphate Anionsmentioning

confidence: 99%

Section: Anionic Complexes: Supercomplex Formationmentioning

confidence: 99%

mentioning

confidence: 99%

See 2 more Smart Citations

Aspects of Anion Coordination from Historical Perspectives

Bianchi¹,

Bowman‐James²,

Garc³

2011

Anion Coordination Chemistry

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“…[5][6][7] Based on different phenomenon of photophysics [8][9][10] various synthetic organic scaffolds containing a suitable receptor site such as, urea, 11 thiourea, 12 amides, 13 macrocyclic ammonium/guanidinium, 14 phenylhydrazone, 15 indole, 16 pyrrole, 17,18 phenol, 19 1,2-diaminoanthraquinone 20 and 4-amino-1,8-naphthalimide derivatives 21 have been designed and developed for favorable naked-eye sensitive, ion-receptor interaction studies. Although much has been achieved however, the chromo and fluorogenic chemosensors that are capable to detect fluoride specifically are limited in number.…”

Section: Introductionmentioning

confidence: 99%

A simple naphthalimide-based receptor for selective recognition of fluoride anion

Misra¹,

Shahid²,

Dwivedi³

et al. 2012

Arkivoc

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Synthesis of a simple fluorescent naphthalimide based receptor 4-aminobenzyl-N-methyl-1,8-naphthalimide 3 was carried out as a selective fluoride ion sensor. In acetonitrile, interaction of 3 with different anions such as, AcO -, F -, Cl -, Br -, I -, and SCN -revealed significant fluorescence quenching only with the F -anion. In the presence of the fluoride anion, the color of the solution changed from a fluorescent green to violet and this was visible to the naked eye. The probable mode of sensing mechanism by photo-induced electron transfer (PET) reaction is attributed to deprotonation of acidic NH proton in the presence of fluoride which was confirmed by change in optical properties intramolecular charge transfer (ICT) and 1 H NMR spectral data analysis. TheJob's plot analysis displayed a 1:1 stoichiometry for interaction between 3 and F -. The extent of fluorescence quenching was estimated by Stern-Volmer plot.

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Schiff Base and Reduced Schiff Base Ligands

Sreenivasulu

2012

Supramolecular Chemistry

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Supramolecular chemistry of Schiff base ligands and their reduced homologues is rapidly growing and gaining increased attention due to their convenient and straightforward synthetic methods and a wide range of complexation modes with almost all types of metal ions. In fact, the phenomenon of molecular recognition, self‐organization and self‐assembly, and host–guest chemistry through covalent and noncovalent interactions is pivotal to the understanding and development of supramolecular chemistry. In this direction, several forms of acyclic and macrocyclic Schiff bases and their reduced forms are employed to gain more insights and correctly ascertain the effect of different donor atoms, their relative position, the number and size of the chelating rings formed, the flexibility, and the geometry around the coordinating moiety on the molecular recognition process and selective binding of cations, anions, and/or neutral species. In this connection, this chapter deals with the supramolecular and molecular recognition properties and interesting host–guest complexes and metalla–supramolecular network structures derived from several acyclic and cyclic Schiff bases and reduced Schiff base ligands. Various solid‐state metalla‐supramolecular network structures are delineated ranging from hydrogen‐bonded linear polymers and helical coordination polymers, and 2D sheets to 3D network architectures constructed via N H⋯O, C O⋯H O solvent , O H⋯O, N H⋯O C, hydrogen bonds and C O⋯π, C H⋯π, and π–π stacking interactions. This review gives an account of the observed structural diversity in relation to the role of different donors and acceptors, aqua ligands and solvents, nature of the ligands and metal ions, and the coordination geometry around the metal ions.

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Influence of dimensionality and charge on anion binding in amide-based macrocyclic receptors

Cited by 197 publications

References 84 publications

Aspects of Anion Coordination from Historical Perspectives

Aspects of Anion Coordination from Historical Perspectives

A simple naphthalimide-based receptor for selective recognition of fluoride anion

Schiff Base and Reduced Schiff Base Ligands

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