10.1021/acs.joc.8b00135.s003 S. Maryamdokht Taimoory S. Maryamdokht Taimoory S. Iraj Sadraei S. Iraj Sadraei Rose Anne Fayoumi Rose Anne Fayoumi Sarah Nasri Sarah Nasri Matthew Revington Matthew Revington John F. Trant John F. Trant Preparation and Characterization of a Small Library of Thermally-Labile End-Caps for Variable-Temperature Triggering of Self-Immolative Polymers American Chemical Society 2018 bone repair maleimide temperature dependence cell culture systems ranges self-immolative polymers application Self-Immolative Polymers Small Library Thermally-Labile End-Caps monosubstituted furans substrate modification 1 H NMR analyses self-healing materials cycloreversion reactions 2018-03-28 00:00:00 Journal contribution https://acs.figshare.com/articles/journal_contribution/Preparation_and_Characterization_of_a_Small_Library_of_Thermally-Labile_End-Caps_for_Variable-Temperature_Triggering_of_Self-Immolative_Polymers/6083093 The reaction between furans and maleimides has increasingly become a method of interest as its reversibility makes it a useful tool for applications ranging from self-healing materials, to self-immolative polymers, to hydrogels for cell culture and for the preparation of bone repair. However, most of these applications have relied on simple monosubstituted furans and simple maleimides and have not extensively evaluated the potential thermal variability inherent in the process that is achievable through simple substrate modification. A small library of cycloadducts suitable for the above applications was prepared, and the temperature dependence of the retro-Diels–Alder processes was determined through <i>in situ</i> <sup>1</sup>H NMR analyses complemented by computational calculations. The practical range of the reported systems ranges from 40 to >110 °C. The cycloreversion reactions are more complex than would be expected based on simple trends expected based on frontier molecular orbital analyses of the materials.