Non-covalent binding of sensitizers for lanthanide(III) luminescence in an EDTA-bis(b-cyclodextrin) ligand

Research output: Contribution to journalArticleAcademicpeer-review

79 Citations (Scopus)

Abstract

EDTA-linked ß-cyclodextrin dimer 3 was synthesized from EDTA bis(anhydride) 1 and mono(propylamino)-appended -cyclodextrin 2. p-tert-Butylbenzoate 5, bound by the ß-cyclodextrin cavities of 3 with an association constant of 104 M-1 in water, acts as a sensitizer for the EuIII and TbIII complexes of 3. Luminescence spectroscopy, microcalorimetry, and GdIII-induced NMR relaxation rate measurements prove that 3 forms a 1:2 complex with 5 and that one of the -cyclodextrin-bound sensitizers coordinates to the EDTA-encapsulated LnIII ion. The EuIII complex of 3 forms strong 1:1 complexes (K = 107 M-1) with bis(propylamido adamantyl)-functionalized biphenyl sensitizers 7 and 8 in water. Both ß-cyclodextrins of 3 are involved in the binding of these guests. The amide functionality adjacent to the biphenyl unit in 7 and 8 coordinates to the EDTA-encapsulated LnIII ion. For these biphenyl-based antennae both binding to ß-cyclodextrin and coordination to the LnIII center are crucial for efficient sensitization
Original languageUndefined
Pages (from-to)2056-2064
JournalJournal of the American Chemical Society
Volume124
Issue number9
DOIs
Publication statusPublished - 2002

Keywords

  • METIS-206200
  • IR-37941

Cite this

@article{fa1dbf2389e441de8e2e23e575986052,
title = "Non-covalent binding of sensitizers for lanthanide(III) luminescence in an EDTA-bis(b-cyclodextrin) ligand",
abstract = "EDTA-linked {\ss}-cyclodextrin dimer 3 was synthesized from EDTA bis(anhydride) 1 and mono(propylamino)-appended -cyclodextrin 2. p-tert-Butylbenzoate 5, bound by the {\ss}-cyclodextrin cavities of 3 with an association constant of 104 M-1 in water, acts as a sensitizer for the EuIII and TbIII complexes of 3. Luminescence spectroscopy, microcalorimetry, and GdIII-induced NMR relaxation rate measurements prove that 3 forms a 1:2 complex with 5 and that one of the -cyclodextrin-bound sensitizers coordinates to the EDTA-encapsulated LnIII ion. The EuIII complex of 3 forms strong 1:1 complexes (K = 107 M-1) with bis(propylamido adamantyl)-functionalized biphenyl sensitizers 7 and 8 in water. Both {\ss}-cyclodextrins of 3 are involved in the binding of these guests. The amide functionality adjacent to the biphenyl unit in 7 and 8 coordinates to the EDTA-encapsulated LnIII ion. For these biphenyl-based antennae both binding to {\ss}-cyclodextrin and coordination to the LnIII center are crucial for efficient sensitization",
keywords = "METIS-206200, IR-37941",
author = "J.J. Michels and Jurriaan Huskens and David Reinhoudt",
note = "677",
year = "2002",
doi = "10.1021/ja017025y",
language = "Undefined",
volume = "124",
pages = "2056--2064",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "9",

}

Non-covalent binding of sensitizers for lanthanide(III) luminescence in an EDTA-bis(b-cyclodextrin) ligand. / Michels, J.J.; Huskens, Jurriaan; Reinhoudt, David.

In: Journal of the American Chemical Society, Vol. 124, No. 9, 2002, p. 2056-2064.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - Non-covalent binding of sensitizers for lanthanide(III) luminescence in an EDTA-bis(b-cyclodextrin) ligand

AU - Michels, J.J.

AU - Huskens, Jurriaan

AU - Reinhoudt, David

N1 - 677

PY - 2002

Y1 - 2002

N2 - EDTA-linked ß-cyclodextrin dimer 3 was synthesized from EDTA bis(anhydride) 1 and mono(propylamino)-appended -cyclodextrin 2. p-tert-Butylbenzoate 5, bound by the ß-cyclodextrin cavities of 3 with an association constant of 104 M-1 in water, acts as a sensitizer for the EuIII and TbIII complexes of 3. Luminescence spectroscopy, microcalorimetry, and GdIII-induced NMR relaxation rate measurements prove that 3 forms a 1:2 complex with 5 and that one of the -cyclodextrin-bound sensitizers coordinates to the EDTA-encapsulated LnIII ion. The EuIII complex of 3 forms strong 1:1 complexes (K = 107 M-1) with bis(propylamido adamantyl)-functionalized biphenyl sensitizers 7 and 8 in water. Both ß-cyclodextrins of 3 are involved in the binding of these guests. The amide functionality adjacent to the biphenyl unit in 7 and 8 coordinates to the EDTA-encapsulated LnIII ion. For these biphenyl-based antennae both binding to ß-cyclodextrin and coordination to the LnIII center are crucial for efficient sensitization

AB - EDTA-linked ß-cyclodextrin dimer 3 was synthesized from EDTA bis(anhydride) 1 and mono(propylamino)-appended -cyclodextrin 2. p-tert-Butylbenzoate 5, bound by the ß-cyclodextrin cavities of 3 with an association constant of 104 M-1 in water, acts as a sensitizer for the EuIII and TbIII complexes of 3. Luminescence spectroscopy, microcalorimetry, and GdIII-induced NMR relaxation rate measurements prove that 3 forms a 1:2 complex with 5 and that one of the -cyclodextrin-bound sensitizers coordinates to the EDTA-encapsulated LnIII ion. The EuIII complex of 3 forms strong 1:1 complexes (K = 107 M-1) with bis(propylamido adamantyl)-functionalized biphenyl sensitizers 7 and 8 in water. Both ß-cyclodextrins of 3 are involved in the binding of these guests. The amide functionality adjacent to the biphenyl unit in 7 and 8 coordinates to the EDTA-encapsulated LnIII ion. For these biphenyl-based antennae both binding to ß-cyclodextrin and coordination to the LnIII center are crucial for efficient sensitization

KW - METIS-206200

KW - IR-37941

U2 - 10.1021/ja017025y

DO - 10.1021/ja017025y

M3 - Article

VL - 124

SP - 2056

EP - 2064

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 9

ER -