Synthesis of upper rim functionalized ...

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Title Synthesis of upper rim functionalized calixarene-based poly(Norbornenes).
Author(s) Alaa S. Abd-El-Aziz, Patrick O. Shipman, Jessica L. Pilfold, Paul R. Shipley
Journal Macromolecular Chemistry and Physics,
Date 2010
Volume 211
Issue 9
Start page 996
End page 1002
Abstract A modified synthesis of 25-allyl-26,27,28-trihydroxycalix[4]arene is reported. This calix[4]arene was utilized to prepare calix[4]arenes containing norbornene and calix[4]arene containing azo dyes and norbornene on their upper rims. The calixarene monomers were reacted with Grubbs' second generation catalyst to give poly(norbornenes) containing calixarenes. The poly(norbornenes) were determined to possess molecular weights between 45 100 and 116 200 with PDIs between 1.4 and 1.9. Thermal analysis showed that the azo dye containing polymers were less thermally stable than the non-azo dye containing polymers with decompositions beginning at 140 °C and 395 °C, respectively. The azo dye containing polymers displayed λmax at 430 nm in THF solutions that underwent a bathochromic shift to 520 nm when acidified with HCl(g), due to the formation of the azonium ion.
DOI 10.1002/macp.200900588

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