Synthesis and Binding Properties of Anion Receptors Containing Multiple Hydorgen Bond Donors

Kyu-Sung Jeong, Ji-Yeon Lee, Min-Hee Lee

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

Full Article Figures & data References Citations Metrics Reprints & Permissions PDF Abstract A new biindolyl scaffold, 7,7′-diamino-2,2′-biindolyl, 2 was efficiently synthesized and modified into anion receptors 9 and 10 with extended hydrogen bond donors. The receptor 9 possesses two indole NHs and two amide NHs, while 10 contains two indole NHs and four urea NHs. The receptors 9 and 10 bind oxoanions such as phosphates and carboxylates by multiple hydrogen bonds in DMSO, both of which bind two or three orders of magnitudes higher than does a reference molecule 8 with only two indole NHs. In addition, binding affinities of 10 with a series of dicarboxylates were also investigated, showing the association constants in between 1.6 × 105 M− 1 (malonate) and 8.1 × 105 M− 1 (adipate) in 10% (v/v) MeOH/DMSO at 22 ± 1°C.
Original languageEnglish
Pages (from-to)257-263
Number of pages7
JournalSupramolecular Chemistry
Volume19
Issue number4-5
DOIs
Publication statusPublished - 2007 Aug 14

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Anions
Dimethyl Sulfoxide
Hydrogen bonds
Scaffolds
Amides
Urea
Phosphates
Association reactions
Molecules
indole
adipic acid
malonic acid

Cite this

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abstract = "Full Article Figures & data References Citations Metrics Reprints & Permissions PDF Abstract A new biindolyl scaffold, 7,7′-diamino-2,2′-biindolyl, 2 was efficiently synthesized and modified into anion receptors 9 and 10 with extended hydrogen bond donors. The receptor 9 possesses two indole NHs and two amide NHs, while 10 contains two indole NHs and four urea NHs. The receptors 9 and 10 bind oxoanions such as phosphates and carboxylates by multiple hydrogen bonds in DMSO, both of which bind two or three orders of magnitudes higher than does a reference molecule 8 with only two indole NHs. In addition, binding affinities of 10 with a series of dicarboxylates were also investigated, showing the association constants in between 1.6 × 105 M− 1 (malonate) and 8.1 × 105 M− 1 (adipate) in 10{\%} (v/v) MeOH/DMSO at 22 ± 1°C.",
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Synthesis and Binding Properties of Anion Receptors Containing Multiple Hydorgen Bond Donors. / Jeong, Kyu-Sung; Lee, Ji-Yeon; Lee, Min-Hee.

In: Supramolecular Chemistry, Vol. 19, No. 4-5, 14.08.2007, p. 257-263.

Research output: Contribution to journalArticle

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AB - Full Article Figures & data References Citations Metrics Reprints & Permissions PDF Abstract A new biindolyl scaffold, 7,7′-diamino-2,2′-biindolyl, 2 was efficiently synthesized and modified into anion receptors 9 and 10 with extended hydrogen bond donors. The receptor 9 possesses two indole NHs and two amide NHs, while 10 contains two indole NHs and four urea NHs. The receptors 9 and 10 bind oxoanions such as phosphates and carboxylates by multiple hydrogen bonds in DMSO, both of which bind two or three orders of magnitudes higher than does a reference molecule 8 with only two indole NHs. In addition, binding affinities of 10 with a series of dicarboxylates were also investigated, showing the association constants in between 1.6 × 105 M− 1 (malonate) and 8.1 × 105 M− 1 (adipate) in 10% (v/v) MeOH/DMSO at 22 ± 1°C.

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