Vanillin and o-vanillin oligomers as models for dendrimer disassembly

Robert M. Kevwitch, Charles S. Shanahan, Dominic V. McGrath

Research output: Contribution to journalArticle

17 Scopus citations

Abstract

Linear analogs have been synthesized to model disassembling dendrimers. These linear analogs provide a facile synthesis to molecules that can be used to test new trigger groups and cleavage vectors. Vanillin and o-vanillin were used as the monomer units of these analogs and two trigger groups, allyl and o-nitrobenzyl, were chosen to test the disassembly process. Allyl triggered analogs 1a-d and 3a-d and o-nitrobenzyl triggered analogs 2a-c and 4a-c showed good to excellent disassembly as followed by the evolution of p-nitrophenoxide reporter ion by UV-Visible spectroscopy. The rate and yield of disassembly was shown to depend on experimental conditions as well as length of the cleavage vector.

Original languageEnglish (US)
Pages (from-to)492-505
Number of pages14
JournalNew Journal of Chemistry
Volume36
Issue number2
DOIs
StatePublished - Feb 1 2012

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Materials Chemistry

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