Cucurbiturils as versatile receptors for redox active substrates

Angel Kaifer, Wei Li, Song Yi

Research output: Contribution to journalArticle

37 Citations (Scopus)

Abstract

Research on the chemistry of cucurbit[n]uril (CBn) hosts has picked up and maintained an impressive pace in the last decade, primarily due to the isolation of hosts with relatively larger cavity sizes, such as CB7 and CB8. This review article summarizes our involvement in this research effort, with particular emphasis on the binding of redox active guests by the CB7 and CB8 hosts. The binding of 4,4′-bipyridinium (viologen) derivatives was the starting point of our CB research. While methylviologen is encapsulated by CB7, forming a highly symmetric inclusion complex, more hydrophobic viologens are bound by inclusion of one of the terminal N-substituents inside the host cavity. Cationic ferrocene derivatives reach extremely high binding affinities with CB7. Binding by CB8 offers additional possibilities, since this host may accommodate two aromatic units inside its cavity, which can be utilized to exert redox control on the assembly of suitably dendronized guests. From a purely electrochemical standpoint, CB7-included viologens maintain their voltammetric reversibility, but CB7-included ferrocene residues experience a pronounced attenuation of their electron transfer kinetics. We have also applied these binding and electrochemical properties to the design and preparation of switchable, CB-based pseudorotaxanes.

Original languageEnglish
Pages (from-to)496-505
Number of pages10
JournalIsrael Journal of Chemistry
Volume51
Issue number5-6
DOIs
StatePublished - May 1 2011

Fingerprint

Viologens
Substrates
Rotaxanes
Derivatives
Electrochemical properties
Kinetics
Electrons
cucurbituril
Oxidation-Reduction
ferrocene

Keywords

  • Cucurbiturils
  • Electrochemistry
  • Fluorescent sensors
  • j-aggregates
  • Nitroxide probes

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Cucurbiturils as versatile receptors for redox active substrates. / Kaifer, Angel; Li, Wei; Yi, Song.

In: Israel Journal of Chemistry, Vol. 51, No. 5-6, 01.05.2011, p. 496-505.

Research output: Contribution to journalArticle

Kaifer, Angel ; Li, Wei ; Yi, Song. / Cucurbiturils as versatile receptors for redox active substrates. In: Israel Journal of Chemistry. 2011 ; Vol. 51, No. 5-6. pp. 496-505.
@article{010ddd4cf8e9401c95586931df524d3a,
title = "Cucurbiturils as versatile receptors for redox active substrates",
abstract = "Research on the chemistry of cucurbit[n]uril (CBn) hosts has picked up and maintained an impressive pace in the last decade, primarily due to the isolation of hosts with relatively larger cavity sizes, such as CB7 and CB8. This review article summarizes our involvement in this research effort, with particular emphasis on the binding of redox active guests by the CB7 and CB8 hosts. The binding of 4,4′-bipyridinium (viologen) derivatives was the starting point of our CB research. While methylviologen is encapsulated by CB7, forming a highly symmetric inclusion complex, more hydrophobic viologens are bound by inclusion of one of the terminal N-substituents inside the host cavity. Cationic ferrocene derivatives reach extremely high binding affinities with CB7. Binding by CB8 offers additional possibilities, since this host may accommodate two aromatic units inside its cavity, which can be utilized to exert redox control on the assembly of suitably dendronized guests. From a purely electrochemical standpoint, CB7-included viologens maintain their voltammetric reversibility, but CB7-included ferrocene residues experience a pronounced attenuation of their electron transfer kinetics. We have also applied these binding and electrochemical properties to the design and preparation of switchable, CB-based pseudorotaxanes.",
keywords = "Cucurbiturils, Electrochemistry, Fluorescent sensors, j-aggregates, Nitroxide probes",
author = "Angel Kaifer and Wei Li and Song Yi",
year = "2011",
month = "5",
day = "1",
doi = "10.1002/ijch.201100042",
language = "English",
volume = "51",
pages = "496--505",
journal = "Israel Journal of Chemistry",
issn = "0021-2148",
publisher = "Wiley-VCH Verlag",
number = "5-6",

}

TY - JOUR

T1 - Cucurbiturils as versatile receptors for redox active substrates

AU - Kaifer, Angel

AU - Li, Wei

AU - Yi, Song

PY - 2011/5/1

Y1 - 2011/5/1

N2 - Research on the chemistry of cucurbit[n]uril (CBn) hosts has picked up and maintained an impressive pace in the last decade, primarily due to the isolation of hosts with relatively larger cavity sizes, such as CB7 and CB8. This review article summarizes our involvement in this research effort, with particular emphasis on the binding of redox active guests by the CB7 and CB8 hosts. The binding of 4,4′-bipyridinium (viologen) derivatives was the starting point of our CB research. While methylviologen is encapsulated by CB7, forming a highly symmetric inclusion complex, more hydrophobic viologens are bound by inclusion of one of the terminal N-substituents inside the host cavity. Cationic ferrocene derivatives reach extremely high binding affinities with CB7. Binding by CB8 offers additional possibilities, since this host may accommodate two aromatic units inside its cavity, which can be utilized to exert redox control on the assembly of suitably dendronized guests. From a purely electrochemical standpoint, CB7-included viologens maintain their voltammetric reversibility, but CB7-included ferrocene residues experience a pronounced attenuation of their electron transfer kinetics. We have also applied these binding and electrochemical properties to the design and preparation of switchable, CB-based pseudorotaxanes.

AB - Research on the chemistry of cucurbit[n]uril (CBn) hosts has picked up and maintained an impressive pace in the last decade, primarily due to the isolation of hosts with relatively larger cavity sizes, such as CB7 and CB8. This review article summarizes our involvement in this research effort, with particular emphasis on the binding of redox active guests by the CB7 and CB8 hosts. The binding of 4,4′-bipyridinium (viologen) derivatives was the starting point of our CB research. While methylviologen is encapsulated by CB7, forming a highly symmetric inclusion complex, more hydrophobic viologens are bound by inclusion of one of the terminal N-substituents inside the host cavity. Cationic ferrocene derivatives reach extremely high binding affinities with CB7. Binding by CB8 offers additional possibilities, since this host may accommodate two aromatic units inside its cavity, which can be utilized to exert redox control on the assembly of suitably dendronized guests. From a purely electrochemical standpoint, CB7-included viologens maintain their voltammetric reversibility, but CB7-included ferrocene residues experience a pronounced attenuation of their electron transfer kinetics. We have also applied these binding and electrochemical properties to the design and preparation of switchable, CB-based pseudorotaxanes.

KW - Cucurbiturils

KW - Electrochemistry

KW - Fluorescent sensors

KW - j-aggregates

KW - Nitroxide probes

UR - http://www.scopus.com/inward/record.url?scp=79957571121&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79957571121&partnerID=8YFLogxK

U2 - 10.1002/ijch.201100042

DO - 10.1002/ijch.201100042

M3 - Article

AN - SCOPUS:79957571121

VL - 51

SP - 496

EP - 505

JO - Israel Journal of Chemistry

JF - Israel Journal of Chemistry

SN - 0021-2148

IS - 5-6

ER -