Improved iterative synthesis of linearly disassembling dendrons

Adrian Ortiz, Charles S. Shanahan, David T. Sisk, Sujeewa C. Perera, Pallavi Rao, Dominic V. McGrath

Research output: Contribution to journalArticle

12 Scopus citations

Abstract

Figure presented. We report a significant improvement in the synthesis of disassembling dendritic structures by using 4-hydroxy-3-nitrobenzoic acid as the building block. We have prepared multigram quantities of first- through third-generation linearly disassembling dendrons containing a [3-N,4-O]-benzylaryl ether disassembly pathway, capped by a vanillin-derived phenyl allyl ether trigger, and a p-nitrophenoxy (PNP) reporter group. The disassembly process of these materials was initiated by allyl deprotection and monitored by the absorbance of the PNP reporter unit in the UV-vis. Modification of the disassembly conditions for the allyl trigger resulted in decreased disassembly times, decreased incubation time for onset of disassembly from minutes to seconds, and allowed observation of indicative rate differences between generations not seen with the previously reported conditions.

Original languageEnglish (US)
Pages (from-to)6154-6162
Number of pages9
JournalJournal of Organic Chemistry
Volume75
Issue number18
DOIs
StatePublished - Sep 17 2010

ASJC Scopus subject areas

  • Organic Chemistry

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    Ortiz, A., Shanahan, C. S., Sisk, D. T., Perera, S. C., Rao, P., & McGrath, D. V. (2010). Improved iterative synthesis of linearly disassembling dendrons. Journal of Organic Chemistry, 75(18), 6154-6162. https://doi.org/10.1021/jo1009849