A structurally simple self-immolative reagent that provides three distinct, simultaneous responses per detection event

Sean A. Nuñez, Kimy Yeung, Nicole S. Fox, Scott T. Phillips

Research output: Contribution to journalArticle

17 Scopus citations

Abstract

A general design is presented for a stimulus-responsive small molecule that is capable of responding to a specific applied chemical or physical signal by releasing two different types of pendant small molecules and a colorimetric indicator simultaneously. A key aspect of this design is the ease with which these reagents are prepared: typically, only four synthetic steps are required. Moreover, the modular construction strategy provides access to stimuli-responsive reagents that are capable of (i) responding to a variety of applied signals and (ii) releasing a number of different small molecules that contain primary alcohols, secondary alcohols, or phenols. These stimuli-responsive reagents are stable under physiological conditions (neither hydrolysis nor thermal degradation of the reagent occurs in significant quantity), and when they are exposed to the appropriate applied signal, they release both pendant small molecules and the colorimetric indicator completely within hours. Finally, unlike other functional groups, such as carbonates, that are used to connect alcohol-bearing molecules to controlled-release reagents, the linkage described in this article increases in hydrolytic stability (rather than decreases) as the pK a of the pendant alcohol decreases (Figure presented).

Original languageEnglish (US)
Pages (from-to)10099-10113
Number of pages15
JournalJournal of Organic Chemistry
Volume76
Issue number24
DOIs
StatePublished - Dec 16 2011

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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