Optimisation of Self-Immolative Systems: Understanding the Role of the Reporter Group Alexander Gavriel 10.17862/cranfield.rd.10059614.v1 https://cord.cranfield.ac.uk/articles/poster/Optimisation_of_Self-Immolative_Systems_Understanding_the_Role_of_the_Reporter_Group/10059614 <div>Stimuli-responsive materials have become significant targets in advance materials as systems of this type offer great potential to perform a variety of functions in a diverse range of applications that span drug delivery (1), biological and chemical sensors (2), diagnostics (3) and degradable polymers (4).</div><div><br></div><div>Self-immolative (5) systems are comprised of a stable bond between trigger and reporter group, the stability of which is sensitive to particular agents and environments. Recently, we have described (6) the first examples of selective self-immolative systems triggered by a non-acidic electrophilic species to afford a facile colorimetric visual disclosure of toxic electrophilic alkylating agents. </div><div><br></div><div>Through molecular design, we have carried out a systematic study on the reporter group to explore the balance between stability, reactivity and degradation of the self-immolative system. A structure-property relationship was established from the library of stimuli-responsive molecules synthesised, and an improved detector capable of disclosing electrophiles under ambient conditions realised.<br></div><div><br></div><div>References: </div><div>1. M. Roth, O. Green, S. Gnaim and D. Shabat, Chemical Reviews, 2015, 116, 1309-1352.</div><div>2. N. H. Ho, R. Weissleder and C. H. Tung, ChemBioChem, 2007, 8, 560.</div><div>3. E. Sella and D. Shabat, J. Am. Chem. Soc., 2009, 131, 9934.</div><div>4. A. Sagi, R. Weinstain, N. Karton and D. Shabat, J. Am. Chem. Soc., 2008, 130, 5434.</div><div>5. C. A. Blencowe, A. T. Russell, F. Greco, W. Hayes and D. W. Thornthwaite, Polym. Chem., 2011, 2, 773.</div><div>6. A. L. Acton, F. Leroux, A. Feula, K. Melia, M. R. Sambrook, W. Hayes and A. T. Russell, Chem. Commun., 2019, 55, 5219.</div><div><br></div> 2019-11-19 15:35:20 Self-Immolative Colorimetric Disclosure Disclosure of Electrophilic Agents DSDS19 Poster DSDS19 Chemical Engineering not elsewhere classified