A new fluorogenic sensing platform for salicylic acid derivatives based on π-π and NH-π interactions between electron-deficient and electron-rich aromatics

Anup Pandith, Giridhari Hazra, Hong Seok Kim

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

A novel simple fluorescent probe was designed for the recognition of electron-rich salicylic acid derivatives (SAs). The imidazole-appended aminomethyl perylene probe 1 selectively differentiated between electron-rich amino-SAs and electron-deficient nitro-SAs in EtOH, exhibiting the highest selectivity and sensitivity toward 5-aminosalicylic acid (5-ASA) and showing strong 1:1 binding (Ka = 1.37 × 107 M− 1). This high selectivity and sensitivity resulted from the synergistic multiple hydrogen bonding interactions of secondary amine and imidazole units and π-π interactions between electron-rich and electron-deficient rings, along with the unusual NH-π interactions between 5-ASA and the perylene moiety of 1. The limit of detection (LOD) for 5-ASA in EtOH was 0.012 ppb.

Original languageEnglish
Pages (from-to)151-159
Number of pages9
JournalSpectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
Volume178
DOIs
Publication statusPublished - May 5 2017
Externally publishedYes

Keywords

  • 5-Aminosalicylic acid
  • Multiple hydrogen bonding
  • Perylene
  • π-π and NH-π interactions

ASJC Scopus subject areas

  • Analytical Chemistry
  • Atomic and Molecular Physics, and Optics
  • Instrumentation
  • Spectroscopy

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