ROS-triggered degradation of selenide-containing polymers based on selenoxide elimination

Abstract

A degradable ROS responsive selenide-containing block polymer would undergo an oxidation-related elimination and degradation process.

Fluoxetine scaffold to design tandem molecular antioxidants and green catalysts

“…These ndings are in agreement with previous observations by Wang and colleagues. 85 The authors studied the selenoxide elimination reaction in a simple model system by reacting a phenylalkylselenide with 2 equivalents of H 2 O 2 in CD 3 CN, observing the appearance of a signal at 1175.1 ppm in the 77 Se NMR spectrum, which is consistent with the presence of seleninic acid. Our results were further conrmed by ESI-MS experiments, as described in the following.…”

“…S33-S36 † for representative mass spectra), in agreement with the data reported by Wang and colleagues. 85 Finally, MS analysis was also performed on the NMR samples used in the mechanistic study above described. Positive and negative ionisation mode MS spectra acquired on the Fig.…”

Oxidative regulation of the mechanical strength of a C–S bond

“…Relative to polymeric systems that respond to light, 4 heat, 5 pH, 6 force, 7 and other stimuli, [8][9][10] polymers whose properties are responsive to oxidation state play remarkable roles in controlled assembly, 11 self-healing ability, 12 adjusting gel volume, 13 and drug delivery. [14][15][16] Construction of such polymers is achieved through incorporation of oxidizable or reduceable (including, in some circumstances, those can be reversibly switched between two oxidation states) chemical functional units, including ferrocene, 17 selenide/diselenide, 18,19 platinum complexes, sulde, aryl oxalate esters, phenylboronic esters, thioketals, proline, etc. 15 Among these systems, we were drawn to sulde containing polymers, which are easily constructed through thiol-ene "click" reactions, 20 Michael additions, 21 ring-opening of ethylene/propylene sulde 22,23 and other scalable and accessible chemistry pathways.…”

Organoselenium chemistry-based polymer synthesis

“…Xu and his coworkers have reported several works that are focused on selenide functional polymers. [55][56][57][58][59][60][61][62][63] These selenium-containing polymers were synthesized by a general route. Dihydroxy diselenide/selenide reacted with diisocyanate as the middle Se segment, and then a reactive polymer was added into the oligomer Se segment to form the final selenium-containing polymers.…”

“…Moreover, some other analogous works reported by Xu and his coworkers can be found in these literature reports. [55][56][57][58][59][60][61][62][63] Zhu et al introduced the redox responsiveness of selenium polymers into high RI polymers to prepare responsive-RI redox sensors. These polymer structures and their high RI are reviewed in Schemes 3 and 4 and section 4.2.…”