Complexation properties of preorganized receptor molecules for large, neutral guests

Irene Higler; Willem Verboom; Feike de Jong; Frank C.J.M. van Veggel; David N. Reinhoudt

doi:10.1002/jlac.199719970739

Complexation properties of preorganized receptor molecules for large, neutral guests

Irene Higler, Willem Verboom, Feike de Jong, Frank C.J.M. van Veggel, David N. Reinhoudt

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Abstract

Receptor molecules with a preorganized cavity were synthesized by combining two resorcin[4]arene and one calix[4]-arene building block. Based on predictions from a computational study which matches hosts and guests, several steroids, sugar derivatives, and alkaloids were selected for complexation studies. Experimentally the complexation of such guests by these receptor molecules was proven by ¹H-NMR spectroscopy (association constants of 1.0-6.0 × 10² M^-1 in CDCl₃). One of these receptors with four hydroxyl groups forms a dimeric capsule (K_dimer = 11 M^-1 in CDCl3). Evidence for this dimerization comes from ¹H-NMR, FAB MS spectroscopy, and molecular mechanics and dynamics calculations.

Original language	English
Pages (from-to)	1577-1586
Journal	Liebigs Annalen
Volume	1997
Issue number	7
DOIs	https://doi.org/10.1002/jlac.199719970739
Publication status	Published - 1997

Keywords

Resorcin[4]arenes
Host-guest chemistry
Dimerization
Calix[4]arenes

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10.1002/jlac.199719970739

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title = "Complexation properties of preorganized receptor molecules for large, neutral guests",

abstract = "Receptor molecules with a preorganized cavity were synthesized by combining two resorcin[4]arene and one calix[4]-arene building block. Based on predictions from a computational study which matches hosts and guests, several steroids, sugar derivatives, and alkaloids were selected for complexation studies. Experimentally the complexation of such guests by these receptor molecules was proven by 1H-NMR spectroscopy (association constants of 1.0-6.0 × 102 M-1 in CDCl3). One of these receptors with four hydroxyl groups forms a dimeric capsule (Kdimer = 11 M-1 in CDCl3). Evidence for this dimerization comes from 1H-NMR, FAB MS spectroscopy, and molecular mechanics and dynamics calculations.",

keywords = "Resorcin[4]arenes, Host-guest chemistry, Dimerization, Calix[4]arenes",

author = "Irene Higler and Willem Verboom and {de Jong}, Feike and {van Veggel}, {Frank C.J.M.} and Reinhoudt, {David N.}",

year = "1997",

doi = "10.1002/jlac.199719970739",

language = "English",

volume = "1997",

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journal = "Liebigs Annalen",

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publisher = "VCH Verlagsgesellschaft",

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TY - JOUR

T1 - Complexation properties of preorganized receptor molecules for large, neutral guests

AU - Higler, Irene

AU - Verboom, Willem

AU - de Jong, Feike

AU - van Veggel, Frank C.J.M.

AU - Reinhoudt, David N.

PY - 1997

Y1 - 1997

N2 - Receptor molecules with a preorganized cavity were synthesized by combining two resorcin[4]arene and one calix[4]-arene building block. Based on predictions from a computational study which matches hosts and guests, several steroids, sugar derivatives, and alkaloids were selected for complexation studies. Experimentally the complexation of such guests by these receptor molecules was proven by 1H-NMR spectroscopy (association constants of 1.0-6.0 × 102 M-1 in CDCl3). One of these receptors with four hydroxyl groups forms a dimeric capsule (Kdimer = 11 M-1 in CDCl3). Evidence for this dimerization comes from 1H-NMR, FAB MS spectroscopy, and molecular mechanics and dynamics calculations.

AB - Receptor molecules with a preorganized cavity were synthesized by combining two resorcin[4]arene and one calix[4]-arene building block. Based on predictions from a computational study which matches hosts and guests, several steroids, sugar derivatives, and alkaloids were selected for complexation studies. Experimentally the complexation of such guests by these receptor molecules was proven by 1H-NMR spectroscopy (association constants of 1.0-6.0 × 102 M-1 in CDCl3). One of these receptors with four hydroxyl groups forms a dimeric capsule (Kdimer = 11 M-1 in CDCl3). Evidence for this dimerization comes from 1H-NMR, FAB MS spectroscopy, and molecular mechanics and dynamics calculations.

KW - Resorcin[4]arenes

KW - Host-guest chemistry

KW - Dimerization

KW - Calix[4]arenes

U2 - 10.1002/jlac.199719970739

DO - 10.1002/jlac.199719970739

M3 - Article

SN - 0947-3440

VL - 1997

SP - 1577

EP - 1586

JO - Liebigs Annalen

JF - Liebigs Annalen

IS - 7

ER -

Complexation properties of preorganized receptor molecules for large, neutral guests

Abstract

Keywords

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