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Periphery-Functionalized Porous Organic Cages.

Paul S Reiss1, Marc A Little2, Valentina Santolini3

  • 1Green Chemistry Centre of Excellence, Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|October 7, 2016
PubMed
Summary
This summary is machine-generated.

Researchers synthesized novel porous organic cages by modifying a precursor molecule. Functionalization with methyl groups significantly increased surface area, while hydroxyl groups enabled further modifications. Bulky groups led to a larger, non-porous cage structure.

Keywords:
cage compoundscycloiminationgas sorptionmicroporous materials

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Area of Science:

  • Materials Science
  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Porous organic cages (POCs) are crystalline materials with tunable properties.
  • Functionalization of POCs is crucial for tailoring their applications.
  • Controlling self-assembly and porosity in POCs remains a challenge.

Purpose of the Study:

  • To synthesize and characterize new functionalized porous organic cages.
  • To investigate the effect of peripheral functional groups on cage structure, packing, and porosity.
  • To explore the potential for post-synthetic modification and control over self-assembly.

Main Methods:

  • Synthesis of trans-1,2-diaminocyclohexane derivatives.
  • Preparation of three distinct porous organic cages (CC16, CC17, CC18) via functionalization.
  • Characterization using techniques such as NMR spectroscopy, X-ray crystallography, and gas adsorption analysis.

Main Results:

  • CC16, with methyl groups, exhibited frustrated packing and doubled surface area compared to CC3.
  • CC17, with hydroxyl groups, showed permanent porosity and potential for post-synthetic modification.
  • CC18, with bulky groups, formed a larger [8+12] cage but was non-porous due to desolvation-induced collapse.

Conclusions:

  • Peripheral functionalization offers a versatile strategy to tune POC properties.
  • Methyl groups enhance porosity through altered packing, while hydroxyl groups allow for external modification.
  • Steric effects of bulky groups can influence self-assembly but may compromise porosity.