10.1021/acs.joc.8b00135.s001
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
Dataset
https://acs.figshare.com/articles/dataset/Preparation_and_Characterization_of_a_Small_Library_of_Thermally-Labile_End-Caps_for_Variable-Temperature_Triggering_of_Self-Immolative_Polymers/6083099
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.