Facile synthesis of photo-cleavable polymers via Passerini reaction

Abstract

Passerini three-component reaction and multicomponent polymerization (MCP) were demonstrated to be facile methods for the preparation of photo-cleavable polymers, photo- and redox-dually cleavable polymers, as well as block copolymers.

A facile approach to catechol containing UV dismantlable adhesives

“…In our previous reports, we found that the Passerini MCP of a diisocyanide, a dicarboxylic acid and an o-nitrobenzaldehyde could efficiently generate UV degradable polymers, demonstrating that onitrobenzaldehyde is a highly reactive aldehyde towards this polymerization [59,60]. To examine whether the catechol group is compatible with this polymerization process, we first carried out the model Passerini reaction of 3-(3,4-dihydroxyphenyl) propionic acid, 5-ethoxy-2-nitrobenzaldehyde and tert-butyl isocyanide.…”

“…Our recent works demonstrated that the multicomponent polymerization (MCP) of a diisocyanide, a dicarboxylic acid and an o-nitrobenzaldehyde was a straightforward way to synthesize photocleavable polymers [59,60]. The key point was the in-situ formed o-nitrobenzyl ester linkage in the polymer main chain, this linkage can be cleaved upon UV irradiation.…”

Concurrent Oxidation of Alcohols and the Passerini Three‐Component Polymerization for the Synthesis of Functional Poly(ester amide)s

“…In addition, polymer P8 has oligo(ethylene oxide)s as side groups, it may be a new type of thermoresponsive polymer, which may find applications in biomedical science . Polymer P9 contains o ‐nitrobenzyl ester moieties in the main chain, and this type of polymer has been proven to be a UV‐cleavable polymer, which may find applications in cell patterns and drug delivery …”

The Ugi reaction in polymer chemistry: syntheses, applications and perspectives

“…MCRs are those reactions to combine more than two reactants in a sequential manner to give highly selective products that retain majority of the atoms of the starting materials. Although known for over 150 years in organic chemistry, only recently, with Meier's introducing tri-component Passerini reaction into polymer chemistry 21,22 , a series of multicomponent reactions (MCRs) such as Ugi reaction, Biginelli reaction, Kabachnik-Fields (KF) reaction, thiolactone-based reactions etc., have been reconsidered from the perspective of polymer chemistry and ultilized to prepare delicated polymers [23][24][25] . Different from traditional two-component coupling reactions (click reactions etc.…”