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Crystal Field Theory
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Single-Crystal-to-Single-Crystal (SCSC) Linear Polymerization of a Desymmetrized Anthraphane.

Marco Servalli1, Nils Trapp2, A Dieter Schlüter1

  • 1Department of Materials, ETH Zürich, Vladimir-Prelog-Weg 5, 8093, Zürich, Switzerland.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 10, 2018
PubMed
Summary

This study demonstrates rare single-crystal-to-single-crystal linear polymerization of anthracene monomers. This process yields a novel ladder-type polymer with unique stereoisomerism in high yields.

Keywords:
anthracenecrystal engineeringcycloadditioncyclophanesingle-crystal-to-single-crystal polymerization

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Area of Science:

  • Polymer Chemistry
  • Crystallography
  • Photochemistry

Background:

  • Single-crystal-to-single-crystal (SCSC) polymerization is a rare phenomenon enabling precise polymer synthesis.
  • Anthracene derivatives are known to undergo photoinduced cycloaddition reactions.

Purpose of the Study:

  • To report a novel case of SCSC linear polymerization.
  • To synthesize a unique ladder-type polymer from trifunctional anthracene monomers.
  • To investigate the stereoisomerism of the resulting polymer.

Main Methods:

  • Photoinduced [4+4]-cycloaddition reactions.
  • Synthesis and crystal structure analysis of anthraphane-tri(OMe) monomers.
  • Characterization of the resulting polyanthraphane-tri(OMe) polymer.

Main Results:

  • Achieved selective linear polymerization via [4+4]-cycloaddition of anthraphane-tri(OMe) monomers.
  • Obtained quantitative yields of a novel ladder-type polymer in minutes.
  • Observed unprecedented stereoisomerism in the polyanthraphane-tri(OMe) product.
  • Maintained crystal integrity throughout the SCSC polymerization process.

Conclusions:

  • Demonstrated a highly efficient SCSC linear polymerization pathway.
  • The designed monomer facilitates precise polymerization due to optimal crystal packing.
  • The resulting polymer exhibits unique stereoisomeric properties, expanding polymer science knowledge.