Synthesis of Chiral Labtb and Visualization of Its Enantiomeric Excess by Induced Circular Dichroism Imaging

Teppei Yamada, Toshiki Eguchi, Taro Wakiyama, Tetsuya Narushima, Hiromi Okamoto, Nobuo Kimizuka

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Crystalline particles of a microporous, robust, and chiral metal–organic framework (MOF) were synthesized and their enantiomer excess (ee) was visualized for each microparticle by CD imaging. Labtb, a thermally and chemically robust MOF, was employed in this study because it shows a chiral space group. Although Labtb has been obtained as a racemic conglomerate, enantioselective synthesis of Labtb was achieved via a chiral precursor complex consisting of lanthanum and homochiral phenylalanine. Methyl orange (MO) was introduced into the micropores of chiral Labtb, which showed a strong induced CD signal for the absorption band of MO chromophores. High ee of the chiral Labtb was revealed by microscopic CD observation at the particle-level. This result provides a facile way to obtain a robust MOF that has chiral nanospace.

Original languageEnglish
Pages (from-to)6698-6702
Number of pages5
JournalChemistry - A European Journal
Volume25
Issue number27
DOIs
Publication statusPublished - May 10 2019

Fingerprint

Enantiomers
Visualization
Imaging techniques
Lanthanum
Chromophores
Phenylalanine
Absorption spectra
Crystalline materials
methyl orange
Circular Dichroism

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

Cite this

Synthesis of Chiral Labtb and Visualization of Its Enantiomeric Excess by Induced Circular Dichroism Imaging. / Yamada, Teppei; Eguchi, Toshiki; Wakiyama, Taro; Narushima, Tetsuya; Okamoto, Hiromi; Kimizuka, Nobuo.

In: Chemistry - A European Journal, Vol. 25, No. 27, 10.05.2019, p. 6698-6702.

Research output: Contribution to journalArticle

Yamada, Teppei ; Eguchi, Toshiki ; Wakiyama, Taro ; Narushima, Tetsuya ; Okamoto, Hiromi ; Kimizuka, Nobuo. / Synthesis of Chiral Labtb and Visualization of Its Enantiomeric Excess by Induced Circular Dichroism Imaging. In: Chemistry - A European Journal. 2019 ; Vol. 25, No. 27. pp. 6698-6702.
@article{70cf08f3d4614f279c29c880c2bb86dd,
title = "Synthesis of Chiral Labtb and Visualization of Its Enantiomeric Excess by Induced Circular Dichroism Imaging",
abstract = "Crystalline particles of a microporous, robust, and chiral metal–organic framework (MOF) were synthesized and their enantiomer excess (ee) was visualized for each microparticle by CD imaging. Labtb, a thermally and chemically robust MOF, was employed in this study because it shows a chiral space group. Although Labtb has been obtained as a racemic conglomerate, enantioselective synthesis of Labtb was achieved via a chiral precursor complex consisting of lanthanum and homochiral phenylalanine. Methyl orange (MO) was introduced into the micropores of chiral Labtb, which showed a strong induced CD signal for the absorption band of MO chromophores. High ee of the chiral Labtb was revealed by microscopic CD observation at the particle-level. This result provides a facile way to obtain a robust MOF that has chiral nanospace.",
author = "Teppei Yamada and Toshiki Eguchi and Taro Wakiyama and Tetsuya Narushima and Hiromi Okamoto and Nobuo Kimizuka",
year = "2019",
month = "5",
day = "10",
doi = "10.1002/chem.201900329",
language = "English",
volume = "25",
pages = "6698--6702",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "27",

}

TY - JOUR

T1 - Synthesis of Chiral Labtb and Visualization of Its Enantiomeric Excess by Induced Circular Dichroism Imaging

AU - Yamada, Teppei

AU - Eguchi, Toshiki

AU - Wakiyama, Taro

AU - Narushima, Tetsuya

AU - Okamoto, Hiromi

AU - Kimizuka, Nobuo

PY - 2019/5/10

Y1 - 2019/5/10

N2 - Crystalline particles of a microporous, robust, and chiral metal–organic framework (MOF) were synthesized and their enantiomer excess (ee) was visualized for each microparticle by CD imaging. Labtb, a thermally and chemically robust MOF, was employed in this study because it shows a chiral space group. Although Labtb has been obtained as a racemic conglomerate, enantioselective synthesis of Labtb was achieved via a chiral precursor complex consisting of lanthanum and homochiral phenylalanine. Methyl orange (MO) was introduced into the micropores of chiral Labtb, which showed a strong induced CD signal for the absorption band of MO chromophores. High ee of the chiral Labtb was revealed by microscopic CD observation at the particle-level. This result provides a facile way to obtain a robust MOF that has chiral nanospace.

AB - Crystalline particles of a microporous, robust, and chiral metal–organic framework (MOF) were synthesized and their enantiomer excess (ee) was visualized for each microparticle by CD imaging. Labtb, a thermally and chemically robust MOF, was employed in this study because it shows a chiral space group. Although Labtb has been obtained as a racemic conglomerate, enantioselective synthesis of Labtb was achieved via a chiral precursor complex consisting of lanthanum and homochiral phenylalanine. Methyl orange (MO) was introduced into the micropores of chiral Labtb, which showed a strong induced CD signal for the absorption band of MO chromophores. High ee of the chiral Labtb was revealed by microscopic CD observation at the particle-level. This result provides a facile way to obtain a robust MOF that has chiral nanospace.

UR - http://www.scopus.com/inward/record.url?scp=85065013337&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85065013337&partnerID=8YFLogxK

U2 - 10.1002/chem.201900329

DO - 10.1002/chem.201900329

M3 - Article

C2 - 30945372

AN - SCOPUS:85065013337

VL - 25

SP - 6698

EP - 6702

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 27

ER -