Microporous Hydrogen-Bonded Organic Framework for Highly Efficient Turn-Up Fluorescent Sensing of Aniline

J Am Chem Soc. 2020 Jul 15;142(28):12478-12485. doi: 10.1021/jacs.0c05277. Epub 2020 Jul 2.


A microporous three-dimensional (3D) hydrogen-bonded organic framework (HOF-20) has been constructed from an aromatic-rich tetratopic carboxylic acid, 5-(2,6-bis(4-carboxyphenyl)pyridin-4-yl)isophthalic acid (H4BCPIA). The activated HOF-20a has a moderately high Brunauer-Emmett-Teller (BET) surface area of 1323 m2 g-1 and excellent stability in water and HCl aqueous solution. HOF-20 exhibits highly efficient turn-up fluorescent sensing of aniline in water with a detection limit of 2.24 μM and is selective toward aniline in the presence of aromatic interferents, owing to the hydrogen bonding and edge-to-face π-π stacking interactions between the HOF-20 host and the guest aniline molecules, as demonstrated in the single-crystal X-ray structure of HOF-20⊃aniline. Density functional theory (DFT) calculations further demonstrate that the recognition of aniline molecules by HOF-20 could restrict the rotation of the aromatic rings in H4BCPIA linkers, reducing the nonradiative decay pathways upon photoexcitation and subsequently enhancing the fluorescence intensity.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Aniline Compounds / analysis*
  • Carboxylic Acids / chemical synthesis
  • Carboxylic Acids / chemistry*
  • Density Functional Theory
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Hydrogen Bonding
  • Molecular Structure
  • Particle Size
  • Porosity
  • Surface Properties
  • Water Pollutants, Chemical / analysis*


  • Aniline Compounds
  • Carboxylic Acids
  • Fluorescent Dyes
  • Water Pollutants, Chemical
  • aniline