Facile conversion of nitrile to amide on polymers of intrinsic microporosity (PIM-1)

Published Date

19 August 2016, Vol.98:244–251, doi:10.1016/j.polymer.2016.06.041

Title 

Facile conversion of nitrile to amide on polymers of intrinsic microporosity (PIM-1)

• Author 

• Paam Yanaranop ^a
• Bagus Santoso ^a
• Ron Etzion ^b
• Jianyong Jin ^a,,

• aSchool of Chemical Sciences, The University of Auckland, Auckland 1142, New Zealand
• bLight Metals Research Centre, The University of Auckland, Auckland 1142, New Zealand

Received 27 April 2016. Revised 12 June 2016. Accepted 16 June 2016. Available online 17 June 2016.

Highlights

• •
  Treatment of PIM-1 with H₂O₂ afforded the PIM-CONH₂ with excellent yield and high purity.
• •
  The structure and properties of PIM-CONH₂ was fully characterized by FT-IR, NMR, UV–Vis and BET surface area etc.
• •
  PIM-CONH₂-24h possessed the apparent BET surface area of 527 m² g⁻¹ after methanol soaking treatment.

Abstract

This paper presents an interesting new development in the area of chemical modification of PIM-1. The amide PIM-1 (named as PIM-CONH₂) was synthesized by post-synthesis modification method using hydrogen peroxide (H₂O₂) as reagent at room temperature. The protocol enjoys mild reaction conditions, easy work-up procedure and high conversion yield (i.e. nearly 100% of nitrile group converts to corresponding amide group.) ¹³C NMR and FT-IR spectra indisputably confirmed that pure PIM-CONH₂ was obtained with no traces of nitrile and carboxylic acid groups. The PIM-CONH₂ conveys high solubility in polar aprotic solvents such as DMSO, DMF, and NMP. The fully-converted sample PIM-CONH₂-24h possessed the apparent BET surface area of 527 m² g⁻¹, which is among the highest ever reported in various post-synthesis modified PIM-1 materials.

Graphical abstract

Keywords

• Polymers of intrinsic microporosity
• Amide
• Nitrogen isotherm

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Scheme 1.

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• ∗ 
  Corresponding author.
  
  

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