Helicates with Ether-Substituted Catechol Esters as Ligands

Christian Mevissen; A. Carel N. Kwamen; Leonard Himmel; Xiaofei Chen; Matthias Brückner; Saskia Huda; Christian Göb; Judith Jenniches; Iris Oppel; Jas S. Ward; Kari Rissanen; Markus Albrecht

doi:10.1002/ejoc.202000843

Helicates with Ether-Substituted Catechol Esters as Ligands

Christian Mevissen, A. Carel N. Kwamen, Leonard Himmel, Xiaofei Chen, Matthias Brückner, Saskia Huda, Christian Göb, Judith Jenniches, Iris Oppel, Jas S. Ward, Kari Rissanen, Markus Albrecht^*

^*Corresponding author for this work

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

6 Citations (Scopus)

Abstract

Mono- or biscatechol esters with ether-type substituents or spacers form either triple lithium bridged dimeric helicates or triple stranded helicates with the ability to bind three lithium cations in their interior. Hierarchical helicates with ether or thioether substituents show in solution a monomer-dimer equilibrium which is independent of the heteroatom in the ester substituent. However, dimerization constants are significantly lower than for corresponding alkyl derivatives. Dinuclear helicates with oligoether spacers are well obtained in the presence of lithium cations. Upon removal of the cations the helicates expand and successive addition of LiCl results in compression again.

Original language	English
Pages (from-to)	5161-5172
Number of pages	12
Journal	European Journal of Organic Chemistry
Volume	2020
Issue number	32
DOIs	https://doi.org/10.1002/ejoc.202000843
Publication status	Published - 31 Aug 2020
Externally published	Yes

Keywords

Catecholate
Helicate
Molecular switch
Templating
Thermodynamics

Access to Document

10.1002/ejoc.202000843

Cite this

@article{76264845757d433faf78c69652004f77,

title = "Helicates with Ether-Substituted Catechol Esters as Ligands",

abstract = "Mono- or biscatechol esters with ether-type substituents or spacers form either triple lithium bridged dimeric helicates or triple stranded helicates with the ability to bind three lithium cations in their interior. Hierarchical helicates with ether or thioether substituents show in solution a monomer-dimer equilibrium which is independent of the heteroatom in the ester substituent. However, dimerization constants are significantly lower than for corresponding alkyl derivatives. Dinuclear helicates with oligoether spacers are well obtained in the presence of lithium cations. Upon removal of the cations the helicates expand and successive addition of LiCl results in compression again.",

keywords = "Catecholate, Helicate, Molecular switch, Templating, Thermodynamics",

author = "Christian Mevissen and Kwamen, {A. Carel N.} and Leonard Himmel and Xiaofei Chen and Matthias Br{\"u}ckner and Saskia Huda and Christian G{\"o}b and Judith Jenniches and Iris Oppel and Ward, {Jas S.} and Kari Rissanen and Markus Albrecht",

note = "Publisher Copyright: {\textcopyright} 2020 The Authors published by Wiley-VCH GmbH",

year = "2020",

month = aug,

day = "31",

doi = "10.1002/ejoc.202000843",

language = "English",

volume = "2020",

pages = "5161--5172",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "32",

}

TY - JOUR

T1 - Helicates with Ether-Substituted Catechol Esters as Ligands

AU - Mevissen, Christian

AU - Kwamen, A. Carel N.

AU - Himmel, Leonard

AU - Chen, Xiaofei

AU - Brückner, Matthias

AU - Huda, Saskia

AU - Göb, Christian

AU - Jenniches, Judith

AU - Oppel, Iris

AU - Ward, Jas S.

AU - Rissanen, Kari

AU - Albrecht, Markus

PY - 2020/8/31

Y1 - 2020/8/31

N2 - Mono- or biscatechol esters with ether-type substituents or spacers form either triple lithium bridged dimeric helicates or triple stranded helicates with the ability to bind three lithium cations in their interior. Hierarchical helicates with ether or thioether substituents show in solution a monomer-dimer equilibrium which is independent of the heteroatom in the ester substituent. However, dimerization constants are significantly lower than for corresponding alkyl derivatives. Dinuclear helicates with oligoether spacers are well obtained in the presence of lithium cations. Upon removal of the cations the helicates expand and successive addition of LiCl results in compression again.

AB - Mono- or biscatechol esters with ether-type substituents or spacers form either triple lithium bridged dimeric helicates or triple stranded helicates with the ability to bind three lithium cations in their interior. Hierarchical helicates with ether or thioether substituents show in solution a monomer-dimer equilibrium which is independent of the heteroatom in the ester substituent. However, dimerization constants are significantly lower than for corresponding alkyl derivatives. Dinuclear helicates with oligoether spacers are well obtained in the presence of lithium cations. Upon removal of the cations the helicates expand and successive addition of LiCl results in compression again.

KW - Catecholate

KW - Helicate

KW - Molecular switch

KW - Templating

KW - Thermodynamics

UR - http://www.scopus.com/inward/record.url?scp=85089311878&partnerID=8YFLogxK

U2 - 10.1002/ejoc.202000843

DO - 10.1002/ejoc.202000843

M3 - Article

AN - SCOPUS:85089311878

SN - 1434-193X

VL - 2020

SP - 5161

EP - 5172

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 32

ER -

Helicates with Ether-Substituted Catechol Esters as Ligands

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this