Ligands for EuIII, FeIII, SrII, and UO2II based on CMPO-functionalized resorcinarene cavitands: synthesis and extraction

Harold Boerrigter; Willem Verboom; David N. Reinhoudt

doi:10.1002/jlac.199719971111

Ligands for Eu^III, Fe^III, Sr^II, and UO₂^II based on CMPO-functionalized resorcinarene cavitands: synthesis and extraction

Harold Boerrigter^*, Willem Verboom, David N. Reinhoudt

^*Corresponding author for this work

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

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Abstract

Partially functionalized cavitands (7a–d) have been synthesized starting from the tetrakis(bromomethyl)cavitand 6. New cavitand‐based cation ligands, with one to three carbamoylmethylphosphane oxide (CMPO) moieties (11a–d), were prepared in good (66–90%) yields. The ligands 11a–d extract Eu^III, but do so less effectively than the tetra‐CMPO cavitand 1. The decreasing number of CMPO groups which result in decreasing extraction percentages for Eu^III, also decrease the selectivity of Eu^III over that of Fe^III, Sr^II, and UO₂^II. There is a difference in extraction behavior, determined by radio‐tracer experiments, between the distal and proximal disubstituted ligands, 11b and 11c, respectively. The extraction constants for the 1:1 complex of 11b and 11c with Eu(picrate)₃ are K_ex = 6.7 · 10⁸ M⁻⁴ and 3.7 · 109 M⁻⁴, respectively.

Original language	English
Pages (from-to)	2247-2254
Journal	Liebigs Annalen
Volume	1997
Issue number	11
DOIs	https://doi.org/10.1002/jlac.199719971111
Publication status	Published - 1997

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@article{b1a50416504442219c8f5e85e4d7a635,

title = "Ligands for EuIII, FeIII, SrII, and UO2II based on CMPO-functionalized resorcinarene cavitands: synthesis and extraction",

abstract = "Partially functionalized cavitands (7a–d) have been synthesized starting from the tetrakis(bromomethyl)cavitand 6. New cavitand‐based cation ligands, with one to three carbamoylmethylphosphane oxide (CMPO) moieties (11a–d), were prepared in good (66–90%) yields. The ligands 11a–d extract EuIII, but do so less effectively than the tetra‐CMPO cavitand 1. The decreasing number of CMPO groups which result in decreasing extraction percentages for EuIII, also decrease the selectivity of EuIII over that of FeIII, SrII, and UO2II. There is a difference in extraction behavior, determined by radio‐tracer experiments, between the distal and proximal disubstituted ligands, 11b and 11c, respectively. The extraction constants for the 1:1 complex of 11b and 11c with Eu(picrate)3 are Kex = 6.7 · 108 M−4 and 3.7 · 109 M−4, respectively.",

author = "Harold Boerrigter and Willem Verboom and Reinhoudt, {David N.}",

year = "1997",

doi = "10.1002/jlac.199719971111",

language = "English",

volume = "1997",

pages = "2247--2254",

journal = "Liebigs Annalen",

issn = "0947-3440",

publisher = "VCH Verlagsgesellschaft",

number = "11",

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TY - JOUR

T1 - Ligands for EuIII, FeIII, SrII, and UO2II based on CMPO-functionalized resorcinarene cavitands

T2 - synthesis and extraction

AU - Boerrigter, Harold

AU - Verboom, Willem

AU - Reinhoudt, David N.

PY - 1997

Y1 - 1997

N2 - Partially functionalized cavitands (7a–d) have been synthesized starting from the tetrakis(bromomethyl)cavitand 6. New cavitand‐based cation ligands, with one to three carbamoylmethylphosphane oxide (CMPO) moieties (11a–d), were prepared in good (66–90%) yields. The ligands 11a–d extract EuIII, but do so less effectively than the tetra‐CMPO cavitand 1. The decreasing number of CMPO groups which result in decreasing extraction percentages for EuIII, also decrease the selectivity of EuIII over that of FeIII, SrII, and UO2II. There is a difference in extraction behavior, determined by radio‐tracer experiments, between the distal and proximal disubstituted ligands, 11b and 11c, respectively. The extraction constants for the 1:1 complex of 11b and 11c with Eu(picrate)3 are Kex = 6.7 · 108 M−4 and 3.7 · 109 M−4, respectively.

AB - Partially functionalized cavitands (7a–d) have been synthesized starting from the tetrakis(bromomethyl)cavitand 6. New cavitand‐based cation ligands, with one to three carbamoylmethylphosphane oxide (CMPO) moieties (11a–d), were prepared in good (66–90%) yields. The ligands 11a–d extract EuIII, but do so less effectively than the tetra‐CMPO cavitand 1. The decreasing number of CMPO groups which result in decreasing extraction percentages for EuIII, also decrease the selectivity of EuIII over that of FeIII, SrII, and UO2II. There is a difference in extraction behavior, determined by radio‐tracer experiments, between the distal and proximal disubstituted ligands, 11b and 11c, respectively. The extraction constants for the 1:1 complex of 11b and 11c with Eu(picrate)3 are Kex = 6.7 · 108 M−4 and 3.7 · 109 M−4, respectively.

U2 - 10.1002/jlac.199719971111

DO - 10.1002/jlac.199719971111

M3 - Article

VL - 1997

SP - 2247

EP - 2254

JO - Liebigs Annalen

JF - Liebigs Annalen

SN - 0947-3440

IS - 11

ER -

Ligands for EuIII, FeIII, SrII, and UO2II based on CMPO-functionalized resorcinarene cavitands: synthesis and extraction

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Ligands for Eu^III, Fe^III, Sr^II, and UO₂^II based on CMPO-functionalized resorcinarene cavitands: synthesis and extraction