Solid-State Complexes of Calix[4]arene Dihydroxyphosphonic Acid with Bipyridyl Ligands

Lazar, Adina N.; Dupont, Nathalie; Navaza, A.; Coleman, Anthony W.

doi:10.1021/cg058017m

Cited by 14 publications

(9 citation statements)

References 18 publications

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“…Adducts of organic acids, for example, phosphonylated calixarene, with free, unprotonated 2,2′bipyridine are known in the literature. 65 Twisted conformation of base molecules changed their role in the adduct. 2,2′-Bipyridine is a connector between 2-fold axis-related hydroxyl groups (O2) from neighboring unit cells.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Extending the Family of Tetrahedral Tectons: Phenyl Embraces in Supramolecular Polymers of Tetraphenylmethane-based Tetraphosphonic Acid Templated by Organic Bases

Zarȩba

Białek

Janczak

et al. 2014

Crystal Growth & Design

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A missing member of the tetraphenylmethane-based family of supramolecular tectons, tetrakis(4-phosphonophenyl)methane, TPPM (1), has been obtained, characterized, and reacted with organic amines that possess modulated conformational flexibility. The obtained adducts serve as a diverse platform for the investigation of the amine templating effect on phenyl embraces, the resulting supramolecular network, and its topology. Hirshfeld surface (HS) analysis has been employed for the investigation of phenyl embraces, which led to the indication of characteristic HS features of 4PE and 6PE phenyl embraces. One can also observe a new subtype of phenyl embrace, namely, HBA-PE (hydrogen bondassisted phenyl embrace), which constitutes the cooperation of two interactions: strong hydrogen bonding and a phenyl embrace. A topological insight into TPPM hydrogen-bonded networks is also provided. As a result, we found a connection of the amine template type with the periodicity of the underlying supramolecular network. Additionally, we report three previously unknown topologies. The obtainment of an unusual example of a phosphonic acid cocrystal with base (adduct 3) allowed for the determination of specific 2D fingerprint plot patterns for acid−base structures, with and without proton transfer.

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Section: ■ Results and Discussionmentioning

confidence: 99%

“…This is probably because 2,2′-bipyridine is a weak base with p K a equal to 4.46 vs 5.22 for pyridine. Adducts of organic acids, for example, phosphonylated calixarene, with free, unprotonated 2,2′-bipyridine are known in the literature …”

Section: Results and Discussionmentioning

confidence: 99%

Extending the Family of Tetrahedral Tectons: Phenyl Embraces in Supramolecular Polymers of Tetraphenylmethane-based Tetraphosphonic Acid Templated by Organic Bases

Zarȩba

Białek

Janczak

et al. 2014

Crystal Growth & Design

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“…In this context, we became interested in the reaction of phosphate monoesters with different bases to study the H-bonding interaction of the resulting ion pair between an anionic phosphate monoester and different counter cations. Although molecular phosphate monoesters mostly form polymeric structures in the solid state, − we have recently reported the syntheses of several bulky aryl-substituted neutral and anionic phosphate monoesters ( 1 – 8 in Scheme ), which exhibit H-bonded dimeric molecular structures analogous to those in carboxylic acids . Through partial blockage of the H-bonding potential of the ArOP(O)(OH) 2 unit by using either a hydrogen-bonding acceptor solvent (such as acetone or acetonitrile) or a hydrogen-bonding donor as counter cation (such as triethylammonium), we were able to realize dimeric supramolecular structures (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Structural Diversity in Supramolecular Organization of Anionic Phosphate Monoesters: Role of Cations

et al. 2019

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Syntheses and structures of anionic arylphosphate monoesters [ArOP(O) 2 (OH)] − (Ar = 2,6-CHPh 2 -4-R-C 6 H 2 ; R = Me/Et/ i Pr/ t Bu) with different counter cations are reported. The counter cations were varied systematically: imidazolium cation, 2-methyl imidazolium cation, N -methyl imidazolium cation, N , N ′-alkyl substituted imidazolium cation, 1,4-diazabicyclo[2.2.2]octan-1-ium cation, 4,4′-bipyridinium dication, and magnesium(II) dication. The objective was to examine if the supramolecular structure of anionic arylphosphate monoesters could be modulated by varying the cation. It was found that an eight-membered P 2 O 4 H 2 -hydrogen-bonded dimeric motif involving intermolecular H-bonding between the [P(O)(OH)] unit of the anionic phosphate monoester along with the counter cation is formed with 2-methyl imidazolium cation, N -methyl imidazolium cation, N , N ′-alkyl substituted imidazolium cation, 1,4-diazabicyclo[2.2.2]octan-1-ium cation, and magnesium(II) dication; both discrete and polymeric H-bonded structures are observed. In the case of imidazolium cations and 1,4-diazabicyclo[2.2.2]octan-1-ium cation, the formation of one-dimensional polymers (single lane/double lane) was observed. On the other hand, two types of phosphate motifs, intermolecular H-bonded dimer and an open-form, were observed in the case of 4,4′-bipyridinium dication.

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“…Among the N , N ′-donors, flexible 1,2-bis(4-pyridyl)ethane ( BPE ) and 1,3-bis(4-pyridyl)propane ( BPP ) represent excellent alternatives for rigid 4,4′-bipyridine in terms of structural research. There are few known crystal complexes of calix-type hosts with these bispyridine compounds …”

Section: Introductionmentioning

confidence: 99%

Structural Diversity in the Crystalline Complexes of para-Sulfonato-calix[4]arene with Bipyridinium Derivatives

Danylyuk

Leśniewska

Suwińska

et al. 2010

Crystal Growth & Design

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The solid-state structures of eight complexes between para-sulfonato-calix[4]arene (C4S) and bipyridinium derivatives, 4,4 0 -bipyridine (BP), 1,2-bis(4-pyridyl)ethane (BPE), and 1,3-bis(4-pyridyl)propane (BPP), have been determined. All the complexes show high degrees of solvation, involving water and ethanol or methanol or acetone. The observed host/guest stoichiometry is determined in part by the nature of the solvent. A wide range of noncovalent interactions are observed in the various complexes, with the dominant interaction being hydrogen bonding and aromatic-aromatic stacking.

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Solid-State Complexes of Calix[4]arene Dihydroxyphosphonic Acid with Bipyridyl Ligands

Cited by 14 publications

References 18 publications

Extending the Family of Tetrahedral Tectons: Phenyl Embraces in Supramolecular Polymers of Tetraphenylmethane-based Tetraphosphonic Acid Templated by Organic Bases

Extending the Family of Tetrahedral Tectons: Phenyl Embraces in Supramolecular Polymers of Tetraphenylmethane-based Tetraphosphonic Acid Templated by Organic Bases

Structural Diversity in Supramolecular Organization of Anionic Phosphate Monoesters: Role of Cations

Structural Diversity in the Crystalline Complexes of para-Sulfonato-calix[4]arene with Bipyridinium Derivatives

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