Guest encapsulation and self-assembly of molecular capsules in polar solvents via multiple ionic interactions

F. Corbellini; R. Fiammengo; P. Timmerman; Mercedes Crego Calama; Kees Versluis; Albert J.R. Heck; Ingrid Luyten; David Reinhoudt

doi:10.1021/ja012058z

Guest encapsulation and self-assembly of molecular capsules in polar solvents via multiple ionic interactions

F. Corbellini, R. Fiammengo, P. Timmerman, Mercedes Crego Calama, Kees Versluis, Albert J.R. Heck, Ingrid Luyten, David Reinhoudt

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Abstract

Herein we report the formation and characterization of a novel type of capsules resulting from the self-association between oppositely charged complementary building blocks in MeOH/H2O. The assembly is based on the interaction between tetraamidinium calix[4]arenes 1a-d and tetrasulfonato calix[4]arene 2. Evidence for the formation of the expected 1:1 assemblies is provided by proton NMR, ESI-MS, and ITC. The association process is fast on the NMR time scale and strongly entropy driven, with association constants in the range of 106 M-1. The system 1a·2 shows binding affinity toward acetylcholine, tetramethylammonium, and N-methylquinuclidinium cations.

Original language	Undefined
Pages (from-to)	6569-6575
Journal	Journal of the American Chemical Society
Volume	124
Issue number	23
DOIs	https://doi.org/10.1021/ja012058z
Publication status	Published - 2002

Keywords

IR-37952
METIS-206211

Access to Document

10.1021/ja012058z

Cite this

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title = "Guest encapsulation and self-assembly of molecular capsules in polar solvents via multiple ionic interactions",

abstract = "Herein we report the formation and characterization of a novel type of capsules resulting from the self-association between oppositely charged complementary building blocks in MeOH/H2O. The assembly is based on the interaction between tetraamidinium calix[4]arenes 1a-d and tetrasulfonato calix[4]arene 2. Evidence for the formation of the expected 1:1 assemblies is provided by proton NMR, ESI-MS, and ITC. The association process is fast on the NMR time scale and strongly entropy driven, with association constants in the range of 106 M-1. The system 1a·2 shows binding affinity toward acetylcholine, tetramethylammonium, and N-methylquinuclidinium cations.",

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author = "F. Corbellini and R. Fiammengo and P. Timmerman and {Crego Calama}, Mercedes and Kees Versluis and Heck, {Albert J.R.} and Ingrid Luyten and David Reinhoudt",

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TY - JOUR

T1 - Guest encapsulation and self-assembly of molecular capsules in polar solvents via multiple ionic interactions

AU - Corbellini, F.

AU - Fiammengo, R.

AU - Timmerman, P.

AU - Crego Calama, Mercedes

AU - Versluis, Kees

AU - Heck, Albert J.R.

AU - Luyten, Ingrid

AU - Reinhoudt, David

N1 - 689

PY - 2002

Y1 - 2002

N2 - Herein we report the formation and characterization of a novel type of capsules resulting from the self-association between oppositely charged complementary building blocks in MeOH/H2O. The assembly is based on the interaction between tetraamidinium calix[4]arenes 1a-d and tetrasulfonato calix[4]arene 2. Evidence for the formation of the expected 1:1 assemblies is provided by proton NMR, ESI-MS, and ITC. The association process is fast on the NMR time scale and strongly entropy driven, with association constants in the range of 106 M-1. The system 1a·2 shows binding affinity toward acetylcholine, tetramethylammonium, and N-methylquinuclidinium cations.

AB - Herein we report the formation and characterization of a novel type of capsules resulting from the self-association between oppositely charged complementary building blocks in MeOH/H2O. The assembly is based on the interaction between tetraamidinium calix[4]arenes 1a-d and tetrasulfonato calix[4]arene 2. Evidence for the formation of the expected 1:1 assemblies is provided by proton NMR, ESI-MS, and ITC. The association process is fast on the NMR time scale and strongly entropy driven, with association constants in the range of 106 M-1. The system 1a·2 shows binding affinity toward acetylcholine, tetramethylammonium, and N-methylquinuclidinium cations.

KW - IR-37952

KW - METIS-206211

U2 - 10.1021/ja012058z

DO - 10.1021/ja012058z

M3 - Article

SN - 0002-7863

VL - 124

SP - 6569

EP - 6575

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 23

ER -