Synthesis and characterization of novel complementary multiple-hydrogen bonded (CMHB) macromolecules via a Michael addition

Koji Yamauchi, Jeremy R. Lizotte, Timothy E. Long

Research output: Contribution to journalArticlepeer-review

83 Scopus citations

Abstract

The synthesis and characterization of novel complementary multiple hydrogen-bonded poly-(styrene) (CMHB-PS) oligomers possessing controlled molecular weights and narrow molecular distributions are described. Novel CMHB-PS oligomers comprising terminal heterocyclic base units were synthesized in a controlled fashion via derivatization of well-defined hydroxyl-terminated PS. The heterocyclic-terminated oligomers were synthesized via a Michael addition of the corresponding heterocyclic compounds such as adenine, thymine, and 2,6-purine with acrylated PS. The acrylated PS precursors were prepared in a quantitative fashion via reaction of hydroxyl-terminated PS with acryloyl chloride in the presence of triethylamine. Terminal heterocyclic bases were introduced via a Michael addition in the presence of potassium tert-butoxide (t-BuOK). Novel CMHB-PS aggregates were prepared via subsequent solution blending of PS with complementary heterocyclic base units. 1H NMR analysis confirmed that a 1:1 mixture of adenine-PS or purine-PS with thymine-PS formed complementary multiple hydrogen bonding and exhibited thermoreversibility. In addition. 1H NMR analysis confirmed that complementary hydrogen bonds dissociated at 95°C in deuterated toluene.

Original languageEnglish (US)
Pages (from-to)8745-8750
Number of pages6
JournalMacromolecules
Volume35
Issue number23
DOIs
StatePublished - Nov 5 2002
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

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