Folding and anion-binding properties of an indolocarbazole dimer with urea appendages

Hyun Joo Kim, Jae Min Suk, Kyu-Sung Jeong

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

An indolocarbazole dimer with the urea functional group was prepared as an anion receptor which contained eight NH hydrogen bonds donors. Two indolocarbazole units were coupled through a butadiynyl linker to allow for helical folding of the resulting dimer by intramolecular hydrogen bonding and dipole-dipole attractions as proven in the 1H NMR spectroscopy. The dimer was found to bind anions (Cl-, Br-, N3 -, AcO-, and) by multiple hydrogen bonds in 10% (v/v) MeOH-acetone, showing high selectivity for sulphate ion. The 1H NMR spectra clearly demonstrated that only indolocarbazole NH protons were involved in the hydrogen bonding with small anions such as chloride, but all of the existing indolocarbazole and urea NHs participated in the hydrogen bonding with sulphate ion. This difference in the binding mode might be responsible for the high affinity and selectivity towards sulphate ion.

Original languageEnglish
Pages (from-to)46-53
Number of pages8
JournalSupramolecular Chemistry
Volume25
Issue number1
DOIs
Publication statusPublished - 2013 Jan 1

Fingerprint

Dimers
Anions
Urea
Hydrogen bonds
Sulfates
Ions
Acetone
Functional groups
Nuclear magnetic resonance spectroscopy
Protons
Chlorides
Nuclear magnetic resonance

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

@article{c5bcecd14fdd4b8f953604c85494e2b6,
title = "Folding and anion-binding properties of an indolocarbazole dimer with urea appendages",
abstract = "An indolocarbazole dimer with the urea functional group was prepared as an anion receptor which contained eight NH hydrogen bonds donors. Two indolocarbazole units were coupled through a butadiynyl linker to allow for helical folding of the resulting dimer by intramolecular hydrogen bonding and dipole-dipole attractions as proven in the 1H NMR spectroscopy. The dimer was found to bind anions (Cl-, Br-, N3 -, AcO-, and) by multiple hydrogen bonds in 10{\%} (v/v) MeOH-acetone, showing high selectivity for sulphate ion. The 1H NMR spectra clearly demonstrated that only indolocarbazole NH protons were involved in the hydrogen bonding with small anions such as chloride, but all of the existing indolocarbazole and urea NHs participated in the hydrogen bonding with sulphate ion. This difference in the binding mode might be responsible for the high affinity and selectivity towards sulphate ion.",
author = "Kim, {Hyun Joo} and Suk, {Jae Min} and Kyu-Sung Jeong",
year = "2013",
month = "1",
day = "1",
doi = "10.1080/10610278.2012.713955",
language = "English",
volume = "25",
pages = "46--53",
journal = "Supramolecular Chemistry",
issn = "1061-0278",
publisher = "Taylor and Francis Ltd.",
number = "1",

}

Folding and anion-binding properties of an indolocarbazole dimer with urea appendages. / Kim, Hyun Joo; Suk, Jae Min; Jeong, Kyu-Sung.

In: Supramolecular Chemistry, Vol. 25, No. 1, 01.01.2013, p. 46-53.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Folding and anion-binding properties of an indolocarbazole dimer with urea appendages

AU - Kim, Hyun Joo

AU - Suk, Jae Min

AU - Jeong, Kyu-Sung

PY - 2013/1/1

Y1 - 2013/1/1

N2 - An indolocarbazole dimer with the urea functional group was prepared as an anion receptor which contained eight NH hydrogen bonds donors. Two indolocarbazole units were coupled through a butadiynyl linker to allow for helical folding of the resulting dimer by intramolecular hydrogen bonding and dipole-dipole attractions as proven in the 1H NMR spectroscopy. The dimer was found to bind anions (Cl-, Br-, N3 -, AcO-, and) by multiple hydrogen bonds in 10% (v/v) MeOH-acetone, showing high selectivity for sulphate ion. The 1H NMR spectra clearly demonstrated that only indolocarbazole NH protons were involved in the hydrogen bonding with small anions such as chloride, but all of the existing indolocarbazole and urea NHs participated in the hydrogen bonding with sulphate ion. This difference in the binding mode might be responsible for the high affinity and selectivity towards sulphate ion.

AB - An indolocarbazole dimer with the urea functional group was prepared as an anion receptor which contained eight NH hydrogen bonds donors. Two indolocarbazole units were coupled through a butadiynyl linker to allow for helical folding of the resulting dimer by intramolecular hydrogen bonding and dipole-dipole attractions as proven in the 1H NMR spectroscopy. The dimer was found to bind anions (Cl-, Br-, N3 -, AcO-, and) by multiple hydrogen bonds in 10% (v/v) MeOH-acetone, showing high selectivity for sulphate ion. The 1H NMR spectra clearly demonstrated that only indolocarbazole NH protons were involved in the hydrogen bonding with small anions such as chloride, but all of the existing indolocarbazole and urea NHs participated in the hydrogen bonding with sulphate ion. This difference in the binding mode might be responsible for the high affinity and selectivity towards sulphate ion.

UR - http://www.scopus.com/inward/record.url?scp=84872346356&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84872346356&partnerID=8YFLogxK

U2 - 10.1080/10610278.2012.713955

DO - 10.1080/10610278.2012.713955

M3 - Article

VL - 25

SP - 46

EP - 53

JO - Supramolecular Chemistry

JF - Supramolecular Chemistry

SN - 1061-0278

IS - 1

ER -