Synthesis and Structural Characterization of a Cyclen-Derived Molecular Cage
Reaction of a tetrafunctionalized cyclen derivative containing four aldehyde groups with an appropriate diamine followed by reduction and demetalation highly efficiently affords a bis(cyclen)-derived molecular cage. Potentiometric investigations show that this compound forms dimetallic complexes with copper(II), with the two metal ions selectively coordinated to the cyclen units. X-ray crystallography indicates that these complexes could give rise to new cascade complexes after incorporation of anions between the metal centers.
Efficient stabilisation of a dihydrogenphosphate tetramer and a dihydrogenpyrophosphate dimer by a cyclic pseudopeptide containing 1,4-disubstituted 1,2,3-triazole moieties
A cyclic pseudooctapeptide 2 is described containing 1,4-disubstituted 1,2,3-triazole moieties. This compound features eight converging hydrogen bond donors along the ring, namely four amide NH and four triazole CH groups, which enable 2 to engage in interactions with anions. While fully deprotonated sulfate anions exhibit only moderate affinity for 2, protonated anions such as dihydrogenpyrophosphate and dihydrogenphosphate anions are strongly bound. Complexation of the phosphate-derived anions involves sandwiching of a dihydrogenpyrophosphate dimer or a dihydrogenphosphate tetramer between two pseudopeptide rings. X-ray crystallography provided structural information, while 1H NMR spectro…
Oxoanion binding to a cyclic pseudopeptide containing 1,4-disubstituted 1,2,3-triazole moieties
A macrocyclic pseudopeptide 3 is described featuring three amide groups and three 1,4-disubstituted 1,2,3-triazole units along the ring. This pseudopeptide was designed such that the amide NH groups and the triazole CH groups converge toward the cavity, thus creating an environment well suited for anion recognition. Conformational studies in solution combined with X-ray crystallography confirmed this preorganisation. Solubility of 3 restricted binding studies to organic media such as 5 vol% DMSO/acetone or DMSO/water mixtures with a water content up to 5 vol%. These binding studies demonstrated that 3 binds to a variety of inorganic anions in DMSO/acetone including chloride, nitrate, sulfat…
Efficient stabilisation of a dihydrogenphosphate tetramer and a dihydrogenpyrophosphate dimer by a cyclic pseudopeptide containing 1,4-disubstituted 1,2,3-triazole moieties† †In memoriam Fritz Vögtle (1939–2017). ‡ ‡Electronic supplementary information (ESI) available: Synthetic details, NMR spectroscopic and MS spectrometric characterisation of 2, NMR spectroscopic and mass spectrometric binding studies, ITC titrations, and crystal structures. CCDC 1555955–1555958. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc02700a Click here for additional data file. Click here for additional data file.
A cyclic pseudooctapeptide binds a dihydrogenpyrophosphate dimer or a cyclic dihydrogenphosphate tetramer by sandwiching these anionic aggregates between two pseudopeptide rings.
Efficient stabilisation of a dihydrogenphosphate tetramer and a dihydrogenpyrophosphate dimer by a cyclic pseudopeptide containing 1,4-disubstituted 1,2,3-triazole moieties
A cyclic pseudooctapeptide 2 is described containing 1,4-disubstituted 1,2,3-triazole moieties. This compound features eight converging hydrogen bond donors along the ring, namely four amide NH and four triazole CH groups, which enable 2 to engage in interactions with anions. While fully deprotonated sulfate anions exhibit only moderate affinity for 2, protonated anions such as dihydrogenpyrophosphate and dihydrogenphosphate anions are strongly bound. Complexation of the phosphate-derived anions involves sandwiching of a dihydrogenpyrophosphate dimer or a dihydrogenphosphate tetramer between two pseudopeptide rings. X-ray crystallography provided structural information, while 1 H NMR spectr…
CCDC 1431346: Experimental Crystal Structure Determination
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CCDC 1555956: Experimental Crystal Structure Determination
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CCDC 1505706: Experimental Crystal Structure Determination
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CCDC 1429442: Experimental Crystal Structure Determination
Related Article: Alexander Ganß, Raquel Belda, Javier Pitarch, Richard Goddard, Enrique García-España, and Stefan Kubik|2015|Org.Lett.|17|5850|doi:10.1021/acs.orglett.5b03027
CCDC 1555958: Experimental Crystal Structure Determination
Related Article: Disha Mungalpara, Arto Valkonen, Kari Rissanen, Stefan Kubik|2017|Chemical Science|8|6005|doi:10.1039/C7SC02700A
CCDC 1504361: Experimental Crystal Structure Determination
Related Article: Disha Mungalpara, Harald Kelm, Arto Valkonen, Kari Rissanen, Sandro Keller, Stefan Kubik|2017|Org.Biomol.Chem.|15|102|doi:10.1039/C6OB02172G
CCDC 1431345: Experimental Crystal Structure Determination
Related Article: Alexander Ganß, Raquel Belda, Javier Pitarch, Richard Goddard, Enrique García-España, and Stefan Kubik|2015|Org.Lett.|17|5850|doi:10.1021/acs.orglett.5b03027
CCDC 1555957: Experimental Crystal Structure Determination
Related Article: Disha Mungalpara, Arto Valkonen, Kari Rissanen, Stefan Kubik|2017|Chemical Science|8|6005|doi:10.1039/C7SC02700A
CCDC 1555955: Experimental Crystal Structure Determination
Related Article: Disha Mungalpara, Arto Valkonen, Kari Rissanen, Stefan Kubik|2017|Chemical Science|8|6005|doi:10.1039/C7SC02700A