Supramolecular polymerization of a ureidopyrimidinone-based [2]catenane prepared via ring-closing metathesis

A.J.P. Teunissen, J.A. Berrocal, C.H.W.A. Corbet, E.W. Meijer

Research output: Contribution to journalArticleAcademicpeer-review

3 Citations (Scopus)
85 Downloads (Pure)

Abstract

The synthesis of a Sauvage-type [2]catenane featuring a quadruple hydrogen bonding ureidopyrimidinone (UPy) motif in each ring was reported. Intermolecular dimerization of the UPy motifs induces the hydrogen-bond-driven supramolecular polymerization of the [2]catenane monomer, thereby creating a linear polymer consisting of both hydrogen bonding and mechanical bonds. As the rings in the UPy catenane are asymmetric, two stereoisomers can be formed upon catenation, that is, with the phenanthroline moieties oriented +90° or -90° with respect to each other. Based on the phenanthroline-Cu(I) and ring-closing metathesis (RCM) approach, we first devised a synthetic procedure for the synthesis of the UPy-based catenane. Here, phenanthroline was first functionalized with phenol moieties in a two-step approach with an overall yield of 46%. The resulting biphenol 3 was then alkylated in a statistical manner with a mixture of 4-bromobut-1-ene and t-Boc-protected bromide resulting in t-Boc-protected compound. The results show that protection of the UPy motifs is necessary for this reaction to reach completion. Analysis of the unprotected UPy catenane by 1H NMR revealed the formation of UPy-UPy dimers and significant broadening of the signals, both in presence and absence of Cu(I).

Original languageEnglish
Pages (from-to)2971-2976
Number of pages6
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume55
Issue number18
DOIs
Publication statusPublished - 15 Sep 2017

Keywords

  • mechanical bond
  • polycatenane
  • ring-closing-metathesis
  • supramolecular polymer
  • ureidopyrimidinone

Fingerprint

Dive into the research topics of 'Supramolecular polymerization of a ureidopyrimidinone-based [2]catenane prepared via ring-closing metathesis'. Together they form a unique fingerprint.

Cite this