Synthesis of Water-Soluble Triazinophanes and Evaluation of Their Molecular Recognition Properties

Shuhei Kusano, Sae Konishi, Ryuta Ishikawa, Norihiro Sato, Satoshi Kawata, Fumi Nagatsugi, Osamu Hayashida

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

Molecular recognition properties of water-soluble triazinophane 1a–1c, derivatized through the straightforward SNAr reaction of common intermediate 5, were explored in aqueous media. Fluorescence titration of 1a–1c by using mono cationic aromatic hydrocarbon G1 and G2 as guests revealed that 1 prefers to form a host–guest complex with pyrene derivative G2 rather than anthracene derivative G1. Complex formation between the derivatives of 1 and G2 were in a 1:1 equimolar ratio with binding constants of ≈ 8 × 103 (m–1), regardless of the substitution groups on the triazine rings. In addition, we found that the molecular recognition of 1 was successfully fine-tuned through post-modification of the triazine rings. With dicationic anthracene G3 as a guest only 1b formed a host–guest complex (Ka = 5.5 × 103 m–1).

Original languageEnglish
Pages (from-to)1618-1623
Number of pages6
JournalEuropean Journal of Organic Chemistry
Volume2017
Issue number12
DOIs
Publication statusPublished - 2017 Mar 27

Keywords

  • Anthracene
  • Host-guest systems
  • Molecular recognition
  • Synthetic methods
  • Triazinophane

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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