An indolocarbazole dimer as a new stereodynamic probe for chiral 1,2-diamines

Hae Geun Jeon, Min Jun Kim, Kyu-Sung Jeong

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

An indolocarbazole dimer that contains aldehyde groups at both ends was prepared by connecting two monomeric units through a rod-like 1,4-butadiynyl spacer. Upon mixing with chiral 1,2-diamines at room temperature, the dimer was in situ converted to the corresponding cyclic diimines in the presence of tetrabutylammonium acetate as a template. The resulting diimines fold to helical conformations of right-handed (P) or left-handed (M) orientations, depending on the absolute stereochemistries of chiral 1,2-diamines. The patterns and intensities of the CD spectra can be used to determine the absolute configurations and enantiomeric excesses of chiral 1,2-diamines.
Original languageEnglish
Pages (from-to)5464-5468
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume12
Issue number29
Publication statusPublished - 2014 May 30

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Diamines
diamines
Dimers
dimers
probes
Stereochemistry
stereochemistry
aldehydes
Aldehydes
spacers
Conformations
acetates
Acetates
rods
templates
Temperature
room temperature
configurations

Cite this

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abstract = "An indolocarbazole dimer that contains aldehyde groups at both ends was prepared by connecting two monomeric units through a rod-like 1,4-butadiynyl spacer. Upon mixing with chiral 1,2-diamines at room temperature, the dimer was in situ converted to the corresponding cyclic diimines in the presence of tetrabutylammonium acetate as a template. The resulting diimines fold to helical conformations of right-handed (P) or left-handed (M) orientations, depending on the absolute stereochemistries of chiral 1,2-diamines. The patterns and intensities of the CD spectra can be used to determine the absolute configurations and enantiomeric excesses of chiral 1,2-diamines.",
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An indolocarbazole dimer as a new stereodynamic probe for chiral 1,2-diamines. / Jeon, Hae Geun; Kim, Min Jun; Jeong, Kyu-Sung.

In: Organic and Biomolecular Chemistry, Vol. 12, No. 29, 30.05.2014, p. 5464-5468.

Research output: Contribution to journalArticle

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AU - Jeon, Hae Geun

AU - Kim, Min Jun

AU - Jeong, Kyu-Sung

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AB - An indolocarbazole dimer that contains aldehyde groups at both ends was prepared by connecting two monomeric units through a rod-like 1,4-butadiynyl spacer. Upon mixing with chiral 1,2-diamines at room temperature, the dimer was in situ converted to the corresponding cyclic diimines in the presence of tetrabutylammonium acetate as a template. The resulting diimines fold to helical conformations of right-handed (P) or left-handed (M) orientations, depending on the absolute stereochemistries of chiral 1,2-diamines. The patterns and intensities of the CD spectra can be used to determine the absolute configurations and enantiomeric excesses of chiral 1,2-diamines.

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