6533b834fe1ef96bd129e0ab
RESEARCH PRODUCT
[N⋅⋅⋅I+⋅⋅⋅N] Halogen-Bonded Dimeric Capsules from Tetrakis(3-pyridyl)ethylene Cavitands
Ngong Kodiah BeyehKari RissanenUlrike WarzokLotta TurunenRakesh PuttreddyChristoph A. Schalleysubject
EthyleneElectrospray ionizationhalogen bonds010402 general chemistryMass spectrometry01 natural sciencesCatalysiscavitandsIonchemistry.chemical_compoundPolymer chemistryOrganic chemistrySpectroscopyta116Alkylmass spectrometrychemistry.chemical_classificationta114010405 organic chemistrydimeric capsulesGeneral MedicineGeneral ChemistryNuclear magnetic resonance spectroscopy0104 chemical scienceschemistryHalogenhalonium ionsdescription
Two [N⋅⋅⋅I+⋅⋅⋅N] halogen-bonded dimeric capsules using tetrakis(3-pyridyl)ethylene cavitands with different lower rim alkyl chains are synthesized and analyzed in solution and the gas phase. These first examples of symmetrical dimeric capsules making use of the iodonium ion (I+) as the main connecting module are characterized by 1H NMR spectroscopy, diffusion ordered NMR spectroscopy (DOSY), electrospray ionization mass spectrometry (ESI-MS), and ion mobility-mass spectrometry (TW-IMS) experiments. The synthesis and effective halogen-bonded dimerization proceeds through analogous dimeric capsules with [N⋅⋅⋅Ag+⋅⋅⋅N] binding motifs as the intermediates as evidenced by the X-ray structures of (CH2Cl2)2@[3 a2⋅Ag4⋅(H2O)2⋅OTs4] and (CH2Cl2)2@[3 a2⋅Ag4⋅(H2O)4⋅OTs4], two structurally different capsules.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2016-10-06 | ANGEWANDTE CHEMIE |