Cryptands with 2,4,6-tris(p-phenylene)-1,3,5-triazine central units and oligoethyleneoxide bridges: synthesis, structure and complexation abilities

Crişan, Cosmin V.; Terec, Anamaria; Hădade, Niculina D.; Grosu, Ion

doi:10.1016/j.tet.2015.07.019

Cited by 3 publications

(4 citation statements)

References 95 publications

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“…As an important class of compounds in host–guest chemistry, cryptands are used to encapsulate large organic guests, such as paraquat derivatives and ammonium salts. Because of the well-defined spatial shapes and cavity sizes, cryptands have shown much higher binding strength toward guest molecules compared to their analogous crown ethers . Because most of the existing cryptand hosts were designed to bind electron-deficient guests, cryptands that could be used to selectively bind electron-rich guests, such as PAHs, are rare .…”

Section: Introductionmentioning

confidence: 79%

A Shape-Persistent Cryptand for Capturing Polycyclic Aromatic Hydrocarbons

Zhang

Liu

et al. 2016

J. Org. Chem.

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A shape-persistent cryptand 1, containing two face-to-face oriented electron-deficient 2,4,6-triphenyl-1,3,5-triazine units separated by approximately 7 Å, and bridged by two rigid 1,8-naphthyridine linkers and a pentaethylene oxide loop, is created for capturing polycyclic aromatic hydrocarbons. Cryptand 1 formed 1:1 complexes with PAH guest molecules, such as phenanthrene (6), anthracene (7), pyrene (8), triphenylene (9), and tetraphene (10). The single-crystal structure of complex 6⊂1 revealed that 6 was included in the cavity of 1 via face-to-face π···π stacking interactions. Soaking crystalline 1 in a toluene solution of anthracene resulted in anthracene from the toluene solution being picked up by the crystalline solid of 1.

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Section: Introductionmentioning

confidence: 79%

A Shape-Persistent Cryptand for Capturing Polycyclic Aromatic Hydrocarbons

Zhang

Liu

et al. 2016

J. Org. Chem.

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“…Cryptand 4 was obtained in good yields (64%) by a nucleophilic substitution reaction using 1,3,5-triazine-2,4,6-triphenol 5 [ 39 , 40 , 41 ] as a nucleophile and 2,6-dibromomethyl-pyridine as a substrate ( Scheme 2 ). The procedure was adapted from the literature using our previous experience with similar reactions [ 2 , 7 , 8 , 42 , 43 ].…”

Section: Resultsmentioning

confidence: 99%

“…Cryptands exhibiting C 3 symmetry have been exciting synthetic targets, due to their high ability to form stable “host–guest” supramolecular assemblies (i.e., as result of the macrobicyclic effect [ 1 ]) either with ions (cations and anions) [ 2 , 3 , 4 ] or neutral organic molecules [ 5 , 6 , 7 , 8 , 9 ]. Many aromatic tripodand units were employed to access this type of cryptand.…”

Section: Introductionmentioning

confidence: 99%

“…Compounds 2 ( a – c ) exhibit a high affinity for alkali (Na + , K + ) and ammonium cations (e.g., dication of 1,5-naphthalenediamine). This complexation behavior is due to the ethyleneoxide groups in the bridges and, in the investigated series, the affinity for K + increased with the number of ethyleneoxide units [ 2 ]. High-affinity, charge–transfer complexes of compound 3 , based on the electron deficient 1,3,5-triazine units (with electron acceptor ability) with electron rich aromatic guests (pyrene, anthracene, 1,5-dinaphthol) were reported, where π–π stacking contacts ensured the formation of the host–guest complexes.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Structure and Supramolecular Properties of a Novel C3 Cryptand with Pyridine Units in the Bridges

et al. 2020

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The high-yield synthesis and the structural investigation of a new cryptand with C3 symmetry, exhibiting 2,4,6-triphenyl-1,3,5-triazine central units and pyridine-based bridges, are reported. The structure of the compound was investigated by single crystal X-ray diffractometry, NMR (nuclear magnetic resonance), HRMS (high resolution mass spectrometry) measurements, and theoretical calculations. The study of supramolecular behavior in solid state revealed the association of cryptand molecules by C-H---π and π---π contacts. Moreover, theoretical calculations indicated the high binding affinity of the cryptand for various organic molecules as guests.

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A three-armed cryptand with triazine and pyridine units: synthesis, structure and complexation with polycyclic aromatic compounds

Lar

Woiczechowski-Pop

Bende

et al. 2018

Beilstein J. Org. Chem.

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The aromatic nucleophilic substitution reaction based synthesis of a three-armed cryptand displaying 2,4,6-triphenyl-1,3,5-triazine units as caps and pyridine rings in the bridges, along with NMR, MS and molecular modelling-based structural analysis of this compound are reported. Appropriate NMR and molecular modelling investigations proved the formation of 1:1 host–guest assemblies between the investigated cryptand and some polynuclear aromatic hydrocarbons or their derivatives.

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Cryptands with 2,4,6-tris(p-phenylene)-1,3,5-triazine central units and oligoethyleneoxide bridges: synthesis, structure and complexation abilities

Cited by 3 publications

References 95 publications

A Shape-Persistent Cryptand for Capturing Polycyclic Aromatic Hydrocarbons

A Shape-Persistent Cryptand for Capturing Polycyclic Aromatic Hydrocarbons

Synthesis, Structure and Supramolecular Properties of a Novel C3 Cryptand with Pyridine Units in the Bridges

A three-armed cryptand with triazine and pyridine units: synthesis, structure and complexation with polycyclic aromatic compounds

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