Anion-induced switching of the helical orientation of a chiral indolocarbazole dimer

Hyun Ji Lee, Hae Geun Jeon, Kyu-Sung Jeong

Research output: Contribution to journalArticle

Abstract

An indolocarbazole dimer, containing chiral urea appendages, that adopts a helically folded conformation by intramolecular hydrogen bonds as proven by 1H NMR and circular dichroism (CD) spectroscopy has been prepared. Owing to the preferential formation of one helical conformer, strong CD signals appear in relatively non-polar solvents such as chloroform (CHCl3) and dichloromethane (CH2Cl2) but the signal is negligible in dimethyl sulfoxide (DMSO). In addition, the optical rotation of the dimer is highly sensitive to the polarity of solvents. For example, the magnitude of the specific rotation (D) is - 934° in CH2Cl2 and - 657° in CHCl3 but it is only - 75° in DMSO. These observations suggest that the dimer folds to a helical structure by intramolecular hydrogen bonds in relatively non-polar solvents but exists in an unfolded extended conformation in polar solvents such as DMSO. The dimer strongly binds anions such as chloride, acetate and sulfate by multiple hydrogen bonds. In addition, anion binding leads to considerable CD spectral changes with the different pattern and degree of Cotton effects depending on the kind of anions. The dimer may be therefore utilised for the construction of an anion-responsive chiroptical sensor or switch.

Original languageEnglish
Pages (from-to)378-385
Number of pages8
JournalSupramolecular Chemistry
Volume27
Issue number5-6
DOIs
Publication statusPublished - 2015 Jun 3

Fingerprint

Dimers
Anions
Dimethyl Sulfoxide
Hydrogen bonds
Dichroism
Conformations
Optical rotation
Circular dichroism spectroscopy
Methylene Chloride
Chloroform
Cotton
Sulfates
Urea
Chlorides
Acetates
Switches
Nuclear magnetic resonance
Sensors

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

@article{0bd353ae5e994359b2e35ebb99124830,
title = "Anion-induced switching of the helical orientation of a chiral indolocarbazole dimer",
abstract = "An indolocarbazole dimer, containing chiral urea appendages, that adopts a helically folded conformation by intramolecular hydrogen bonds as proven by 1H NMR and circular dichroism (CD) spectroscopy has been prepared. Owing to the preferential formation of one helical conformer, strong CD signals appear in relatively non-polar solvents such as chloroform (CHCl3) and dichloromethane (CH2Cl2) but the signal is negligible in dimethyl sulfoxide (DMSO). In addition, the optical rotation of the dimer is highly sensitive to the polarity of solvents. For example, the magnitude of the specific rotation (D) is - 934° in CH2Cl2 and - 657° in CHCl3 but it is only - 75° in DMSO. These observations suggest that the dimer folds to a helical structure by intramolecular hydrogen bonds in relatively non-polar solvents but exists in an unfolded extended conformation in polar solvents such as DMSO. The dimer strongly binds anions such as chloride, acetate and sulfate by multiple hydrogen bonds. In addition, anion binding leads to considerable CD spectral changes with the different pattern and degree of Cotton effects depending on the kind of anions. The dimer may be therefore utilised for the construction of an anion-responsive chiroptical sensor or switch.",
author = "Lee, {Hyun Ji} and Jeon, {Hae Geun} and Kyu-Sung Jeong",
year = "2015",
month = "6",
day = "3",
doi = "10.1080/10610278.2014.941293",
language = "English",
volume = "27",
pages = "378--385",
journal = "Supramolecular Chemistry",
issn = "1061-0278",
publisher = "Taylor and Francis Ltd.",
number = "5-6",

}

Anion-induced switching of the helical orientation of a chiral indolocarbazole dimer. / Lee, Hyun Ji; Jeon, Hae Geun; Jeong, Kyu-Sung.

In: Supramolecular Chemistry, Vol. 27, No. 5-6, 03.06.2015, p. 378-385.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Anion-induced switching of the helical orientation of a chiral indolocarbazole dimer

AU - Lee, Hyun Ji

AU - Jeon, Hae Geun

AU - Jeong, Kyu-Sung

PY - 2015/6/3

Y1 - 2015/6/3

N2 - An indolocarbazole dimer, containing chiral urea appendages, that adopts a helically folded conformation by intramolecular hydrogen bonds as proven by 1H NMR and circular dichroism (CD) spectroscopy has been prepared. Owing to the preferential formation of one helical conformer, strong CD signals appear in relatively non-polar solvents such as chloroform (CHCl3) and dichloromethane (CH2Cl2) but the signal is negligible in dimethyl sulfoxide (DMSO). In addition, the optical rotation of the dimer is highly sensitive to the polarity of solvents. For example, the magnitude of the specific rotation (D) is - 934° in CH2Cl2 and - 657° in CHCl3 but it is only - 75° in DMSO. These observations suggest that the dimer folds to a helical structure by intramolecular hydrogen bonds in relatively non-polar solvents but exists in an unfolded extended conformation in polar solvents such as DMSO. The dimer strongly binds anions such as chloride, acetate and sulfate by multiple hydrogen bonds. In addition, anion binding leads to considerable CD spectral changes with the different pattern and degree of Cotton effects depending on the kind of anions. The dimer may be therefore utilised for the construction of an anion-responsive chiroptical sensor or switch.

AB - An indolocarbazole dimer, containing chiral urea appendages, that adopts a helically folded conformation by intramolecular hydrogen bonds as proven by 1H NMR and circular dichroism (CD) spectroscopy has been prepared. Owing to the preferential formation of one helical conformer, strong CD signals appear in relatively non-polar solvents such as chloroform (CHCl3) and dichloromethane (CH2Cl2) but the signal is negligible in dimethyl sulfoxide (DMSO). In addition, the optical rotation of the dimer is highly sensitive to the polarity of solvents. For example, the magnitude of the specific rotation (D) is - 934° in CH2Cl2 and - 657° in CHCl3 but it is only - 75° in DMSO. These observations suggest that the dimer folds to a helical structure by intramolecular hydrogen bonds in relatively non-polar solvents but exists in an unfolded extended conformation in polar solvents such as DMSO. The dimer strongly binds anions such as chloride, acetate and sulfate by multiple hydrogen bonds. In addition, anion binding leads to considerable CD spectral changes with the different pattern and degree of Cotton effects depending on the kind of anions. The dimer may be therefore utilised for the construction of an anion-responsive chiroptical sensor or switch.

UR - http://www.scopus.com/inward/record.url?scp=84906017110&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84906017110&partnerID=8YFLogxK

U2 - 10.1080/10610278.2014.941293

DO - 10.1080/10610278.2014.941293

M3 - Article

VL - 27

SP - 378

EP - 385

JO - Supramolecular Chemistry

JF - Supramolecular Chemistry

SN - 1061-0278

IS - 5-6

ER -