Superaromatic terpyridines based on corannulene responsive to metal ions

Dalton Trans. 2014 Jan 28;43(4):1753-61. doi: 10.1039/c3dt52013g.

Abstract

Two superaromatic terpyridine ligands (1 and 2) incorporating a corannulene unit at the 4'-position are reported. The optical and metal sensing properties of both ligands were investigated by the naked eye, and UV-vis and fluorescence spectroscopy in this work. In 1, the corannulene motif is directly connected to the 4'-phenylterpyridine domain, while in 2, the corannulene motif and the 4'-phenylterpyridine domain are separated by an acetylene linker. Both 1 and 2 can work as chemosensors for metal ions and display different optical responses to various metal ions. It is shown that both ligands exhibit a colorimetric sensing ability for Fe(2+) through an obvious color change from colorless to magenta, and this color change can be observed easily by the naked eye. The addition of Fe(2+) also leads to significant changes in the absorption spectra of the ligands. A characteristic red shift in the emission spectra is observed in the presence of Zn(2+), which facilitates the discrimination of Zn(2+) from other metal ions. In addition, density functional theory (DFT) and time-dependent-density functional theory (TD-DFT) calculations were performed and shown to be consistent with the observed experimental results.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Metals / chemistry*
  • Polycyclic Aromatic Hydrocarbons / chemistry*
  • Pyridines / chemistry*
  • Spectrometry, Fluorescence
  • Spectrophotometry, Ultraviolet

Substances

  • Metals
  • Polycyclic Aromatic Hydrocarbons
  • Pyridines
  • corannulene