Sensitive fluorescence sensor for nitroaniline isomers based on calix[4]arene bearing naphthyl groups

Novel naphthyl-modified calix[4]arene was synthesized by click chemistry, and exhibited high affinity and selectivity for p-nitroaniline by the fluorescence spectroscopy. However, the sensitivity toward other anilines 3a-e are negligible. The 1H NMR, 1H NOESY, MALDI-TOF mass spectroscopy and computational calculations revealed the formation of host-guest complex driven by H-bonding and hydrophobic interactions.