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[N⋅⋅⋅I + ⋅⋅⋅N] Halogen‐Bonded Dimeric Capsules from Tetrakis(3‐pyridyl)ethylene Cavitands
Author(s) -
Turunen Lotta,
Warzok Ulrike,
Puttreddy Rakesh,
Beyeh Ngong Kodiah,
Schalley Christoph A.,
Rissanen Kari
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201607789
Subject(s) - electrospray ionization , chemistry , ethylene , halogen , mass spectrometry , alkyl , nuclear magnetic resonance spectroscopy , spectroscopy , ion , crystallography , polymer chemistry , stereochemistry , organic chemistry , chromatography , physics , quantum mechanics , catalysis
Abstract 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 1 H 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 (CH 2 Cl 2 ) 2 @[ 3 a 2 ⋅Ag 4 ⋅(H 2 O) 2 ⋅OTs 4 ] and (CH 2 Cl 2 ) 2 @[ 3 a 2 ⋅Ag 4 ⋅(H 2 O) 4 ⋅OTs 4 ], two structurally different capsules.