Selective lithium ion binding involving inositol-based tris(spirotetrahydrofuranyl) ionophores: Formation of a rodlike supramolecular ionic polymer from a homoditopic dimer

L. A. Paquette, J. Tae

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

The stereoselective replacement of all three hydroxyl groups in myo-inositol orthoformate by spirotetrahydrofuran rings in that manner which projects the C-O bonds in the molecular interior has been examined. The heterocyclic components were introduced sequentially, a protocol that demonstrated the utility of precomplexation to LiClO4 as a stereocontrol tactic. The capability of 3 to coordinate to alkali metal ions was quantified. The conformationally restricted nature of this ligand conveys high selectivity for binding to lithium ion. Beyond that, the ionophore prefers to form 2:1 complexes with Li+ and exhibits little tendency for 1:1 stoichiometry. These properties are shared by the "dimer" 36, in which two building blocks of type 3 have been conjoined by a 1,3-butadiyne tether positioned at the ortho ester terminus. This bifacial ligand reacts with one equivalent of LiClO4 or LiBF4 to form rodlike ionic polymers. Alternative recourse to lithium picrate results in production of the doubly capped homoditopic complex 41. Various other aspects of the chemistry peculiar to these systems are discussed.

Original languageEnglish
Pages (from-to)4974-4984
Number of pages11
JournalJournal of the American Chemical Society
Volume123
Issue number21
DOIs
Publication statusPublished - 2001 Oct 9

Fingerprint

Ionophores
Inositol
Lithium
Dimers
Polymers
Ligands
Ions
Alkali Metals
Alkali metals
Stoichiometry
Hydroxyl Radical
Metal ions
Esters
lithium perchlorate
picric acid

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

@article{e07c3fd6625e45819d7ef4bdf395cd37,
title = "Selective lithium ion binding involving inositol-based tris(spirotetrahydrofuranyl) ionophores: Formation of a rodlike supramolecular ionic polymer from a homoditopic dimer",
abstract = "The stereoselective replacement of all three hydroxyl groups in myo-inositol orthoformate by spirotetrahydrofuran rings in that manner which projects the C-O bonds in the molecular interior has been examined. The heterocyclic components were introduced sequentially, a protocol that demonstrated the utility of precomplexation to LiClO4 as a stereocontrol tactic. The capability of 3 to coordinate to alkali metal ions was quantified. The conformationally restricted nature of this ligand conveys high selectivity for binding to lithium ion. Beyond that, the ionophore prefers to form 2:1 complexes with Li+ and exhibits little tendency for 1:1 stoichiometry. These properties are shared by the {"}dimer{"} 36, in which two building blocks of type 3 have been conjoined by a 1,3-butadiyne tether positioned at the ortho ester terminus. This bifacial ligand reacts with one equivalent of LiClO4 or LiBF4 to form rodlike ionic polymers. Alternative recourse to lithium picrate results in production of the doubly capped homoditopic complex 41. Various other aspects of the chemistry peculiar to these systems are discussed.",
author = "Paquette, {L. A.} and J. Tae",
year = "2001",
month = "10",
day = "9",
doi = "10.1021/ja010103x",
language = "English",
volume = "123",
pages = "4974--4984",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "21",

}

TY - JOUR

T1 - Selective lithium ion binding involving inositol-based tris(spirotetrahydrofuranyl) ionophores

T2 - Formation of a rodlike supramolecular ionic polymer from a homoditopic dimer

AU - Paquette, L. A.

AU - Tae, J.

PY - 2001/10/9

Y1 - 2001/10/9

N2 - The stereoselective replacement of all three hydroxyl groups in myo-inositol orthoformate by spirotetrahydrofuran rings in that manner which projects the C-O bonds in the molecular interior has been examined. The heterocyclic components were introduced sequentially, a protocol that demonstrated the utility of precomplexation to LiClO4 as a stereocontrol tactic. The capability of 3 to coordinate to alkali metal ions was quantified. The conformationally restricted nature of this ligand conveys high selectivity for binding to lithium ion. Beyond that, the ionophore prefers to form 2:1 complexes with Li+ and exhibits little tendency for 1:1 stoichiometry. These properties are shared by the "dimer" 36, in which two building blocks of type 3 have been conjoined by a 1,3-butadiyne tether positioned at the ortho ester terminus. This bifacial ligand reacts with one equivalent of LiClO4 or LiBF4 to form rodlike ionic polymers. Alternative recourse to lithium picrate results in production of the doubly capped homoditopic complex 41. Various other aspects of the chemistry peculiar to these systems are discussed.

AB - The stereoselective replacement of all three hydroxyl groups in myo-inositol orthoformate by spirotetrahydrofuran rings in that manner which projects the C-O bonds in the molecular interior has been examined. The heterocyclic components were introduced sequentially, a protocol that demonstrated the utility of precomplexation to LiClO4 as a stereocontrol tactic. The capability of 3 to coordinate to alkali metal ions was quantified. The conformationally restricted nature of this ligand conveys high selectivity for binding to lithium ion. Beyond that, the ionophore prefers to form 2:1 complexes with Li+ and exhibits little tendency for 1:1 stoichiometry. These properties are shared by the "dimer" 36, in which two building blocks of type 3 have been conjoined by a 1,3-butadiyne tether positioned at the ortho ester terminus. This bifacial ligand reacts with one equivalent of LiClO4 or LiBF4 to form rodlike ionic polymers. Alternative recourse to lithium picrate results in production of the doubly capped homoditopic complex 41. Various other aspects of the chemistry peculiar to these systems are discussed.

UR - http://www.scopus.com/inward/record.url?scp=0034808659&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0034808659&partnerID=8YFLogxK

U2 - 10.1021/ja010103x

DO - 10.1021/ja010103x

M3 - Article

C2 - 11457325

AN - SCOPUS:0034808659

VL - 123

SP - 4974

EP - 4984

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 21

ER -