Head-to-head linked double calix[4]arenes: convenient synthesis and complexation properties

Oliver Struck; Lysander A.J. Chrisstoffels; Ronny J.W. Lugtenberg; Willem Verboom; Gerrit J. van Hummel; Sybolt Harkema; David N. Reinhoudt

doi:10.1021/jo962138z

Head-to-head linked double calix[4]arenes: convenient synthesis and complexation properties

Oliver Struck
, Lysander A.J. Chrisstoffels
, Ronny J.W. Lugtenberg
, Willem Verboom
, Gerrit J. van Hummel
, Sybolt Harkema
, David N. Reinhoudt^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

72 Citations (Scopus)

137 Downloads (Pure)

Abstract

Combination of calix[4]arenes functionalized at the upper rim at the 5- and 17-positions with amino and formyl groups, respectively, gives a new series of "head-to-head" linked double calix[4]arenes in nearly quantitative yield. The X-ray structure of a modified double calix[4]arene is reported. The novel, highly preorganized receptor molecules complex silver(I) ions (K_ass = 9.5 × 10⁵ M^-1 in CDCl₃); the selectivity of complexation was studied by supported liquid membrane transport experiments and chemically modified field effect transistor measurements.

Original language	English
Pages (from-to)	2487-2493
Journal	The journal of organic chemistry
Volume	62
Issue number	8
DOIs	https://doi.org/10.1021/jo962138z
Publication status	Published - 1997

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@article{56a1022f21f7422db4659146fe976496,

title = "Head-to-head linked double calix[4]arenes: convenient synthesis and complexation properties",

abstract = "Combination of calix[4]arenes functionalized at the upper rim at the 5- and 17-positions with amino and formyl groups, respectively, gives a new series of {"}head-to-head{"} linked double calix[4]arenes in nearly quantitative yield. The X-ray structure of a modified double calix[4]arene is reported. The novel, highly preorganized receptor molecules complex silver(I) ions (Kass = 9.5 × 105 M-1 in CDCl3); the selectivity of complexation was studied by supported liquid membrane transport experiments and chemically modified field effect transistor measurements.",

author = "Oliver Struck and Chrisstoffels, \{Lysander A.J.\} and Lugtenberg, \{Ronny J.W.\} and Willem Verboom and \{van Hummel\}, \{Gerrit J.\} and Sybolt Harkema and Reinhoudt, \{David N.\}",

year = "1997",

doi = "10.1021/jo962138z",

language = "English",

volume = "62",

pages = "2487--2493",

journal = "The journal of organic chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "8",

}

TY - JOUR

T1 - Head-to-head linked double calix[4]arenes

T2 - convenient synthesis and complexation properties

AU - Struck, Oliver

AU - Chrisstoffels, Lysander A.J.

AU - Lugtenberg, Ronny J.W.

AU - Verboom, Willem

AU - van Hummel, Gerrit J.

AU - Harkema, Sybolt

AU - Reinhoudt, David N.

PY - 1997

Y1 - 1997

N2 - Combination of calix[4]arenes functionalized at the upper rim at the 5- and 17-positions with amino and formyl groups, respectively, gives a new series of "head-to-head" linked double calix[4]arenes in nearly quantitative yield. The X-ray structure of a modified double calix[4]arene is reported. The novel, highly preorganized receptor molecules complex silver(I) ions (Kass = 9.5 × 105 M-1 in CDCl3); the selectivity of complexation was studied by supported liquid membrane transport experiments and chemically modified field effect transistor measurements.

AB - Combination of calix[4]arenes functionalized at the upper rim at the 5- and 17-positions with amino and formyl groups, respectively, gives a new series of "head-to-head" linked double calix[4]arenes in nearly quantitative yield. The X-ray structure of a modified double calix[4]arene is reported. The novel, highly preorganized receptor molecules complex silver(I) ions (Kass = 9.5 × 105 M-1 in CDCl3); the selectivity of complexation was studied by supported liquid membrane transport experiments and chemically modified field effect transistor measurements.

U2 - 10.1021/jo962138z

DO - 10.1021/jo962138z

M3 - Article

SN - 0022-3263

VL - 62

SP - 2487

EP - 2493

JO - The journal of organic chemistry

JF - The journal of organic chemistry

IS - 8

ER -

Head-to-head linked double calix[4]arenes: convenient synthesis and complexation properties

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