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Indoles and Related Heterocycles

  • Hemraj Juwarker
  • Jae-min Suk
  • Kyu-Sung JeongEmail author
Chapter
Part of the Topics in Heterocyclic Chemistry book series (TOPICS, volume 24)

Abstract

Indole and the related heterocycles have emerged as efficient building blocks for the creation of novel anion receptors. This chapter focuses on the employment of indoles, carbazoles, and indolocarbazoles in the creation of molecular clefts, macrocycles, oligomers, and sensors. The majority of these structures utilize the heterocyclic NH as a hydrogen bond donor in binding to anions of various sizes and geometries. These heterocycles are often connected by amides and ureas which also function as hydrogen bond donors in anion binding. Finally, molecular sensors based on indoles and carbazoles have been described, showing color or fluorescence changes upon anion binding or deprotonation of the heterocyclic NH by basic anions.

Keywords

Anion recognition Carbazole Hydrogen bond Indole Indolocarbazole Macrocycle Molecular cleft Molecular sensor Oligomer 

Abbreviations

AcO

Acetate

Bz

Benzyl

BzO

Benzoate

CD

Circular dichroism

CIC

Chloride ion channel

CIS

Complexation induced shift

DABCO

1,4-Diazabicyclo[2.2.2]octane

DMSO

Dimethyl sulfoxide

Ka

Association constant

Kd

Dissociation constant

NMR

Nuclear magnetic resonance

NrtA

Nitrate-binding protein

phen

Phenanthroline

SBP

Sulfate-binding protein

Ser

Serine

TBA

Tetrabutylammonium

THF

Tetrahydrofuran

Trp

Tryptophan

UV/Vis

Ultraviolet/visible

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Copyright information

© Springer-Verlag Berlin Heidelberg 2010

Authors and Affiliations

  1. 1.Department of ChemistryYonsei UniversitySeoulKorea

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