Issue 2, 2012

Vanillin and o-vanillin oligomers as models for dendrimer disassembly

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.

Graphical abstract: Vanillin and o-vanillin oligomers as models for dendrimer disassembly

Supplementary files

Article information

Article type
Paper
Submitted
30 Sep 2011
Accepted
10 Nov 2011
First published
08 Dec 2011

New J. Chem., 2012,36, 492-505

Vanillin and o-vanillin oligomers as models for dendrimer disassembly

R. M. Kevwitch, C. S. Shanahan and D. V. McGrath, New J. Chem., 2012, 36, 492 DOI: 10.1039/C1NJ20841A

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