Synthesis of Bridged Indigos and Their Thermoisomerization and Photoisomerization Behaviors

Synthesis of Bridged Indigos and Their Thermoisomerization and Photoisomerization Behaviors

Bridged indigos were synthesized by bridging the two nitrogen atoms in the indigo structure with a carbon chain, and their properties were carefully examined. These bridged indigos have intrinsic planar chirality, and the enantiomers were separated using chiral high-performance liquid chromatography...

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Veröffentlicht in:Journal of organic chemistry 2021-12, Vol.86 (24), p.17620-17628
Hauptverfasser: Kanda, Junya, Egami, Naoki, Sasamori, Takahiro, Imayoshi, Ayumi, Hosoya, Takashi, Tsubaki, Kazunori
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Sprache:eng
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Chromatography, High Pressure Liquid
Indigo Carmine
Stereoisomerism
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container_end_page 17628
container_issue 24
container_start_page 17620
container_title Journal of organic chemistry
container_volume 86
creator Kanda, Junya
Egami, Naoki
Sasamori, Takahiro
Imayoshi, Ayumi
Hosoya, Takashi
Tsubaki, Kazunori
description Bridged indigos were synthesized by bridging the two nitrogen atoms in the indigo structure with a carbon chain, and their properties were carefully examined. These bridged indigos have intrinsic planar chirality, and the enantiomers were separated using chiral high-performance liquid chromatography. When the chiral bridged indigos were subjected to thermo- and photoisomerization, the corresponding (Z)-indigo was not observed at all, and racemization was observed. This phenomenon is caused by the low activation energy of inversion due to the 1.5 bond order of the double bond of the indigo skeleton and the large energy difference between the ground states of (E)-indigo and (Z)-indigo.
doi_str_mv 10.1021/acs.joc.1c01726
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source American Chemical Society; MEDLINE
subjects Chromatography, High Pressure Liquid
Indigo Carmine
Stereoisomerism
title Synthesis of Bridged Indigos and Their Thermoisomerization and Photoisomerization Behaviors
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