Selective Interfacial Olefin Cross Metathesis for the Preparation of Hollow Nanocapsules

Abstract

The first synthesis of hollow nanocapsules with an aqueous core via olefin cross metathesis is presented. The reaction was tailored such that it proceeds selectively at the oil–water interface of aqueous nanodroplets in an inverse miniemulsion. The cross metathesis takes place between an acrylated polysaccharide and unsaturated organophosphates under mild conditions. This general protocol allows the synthesis of biocompatible and polyfunctional nanocapsules via the bioorthogonal olefin metathesis, thus generating a highly versatile methodology for the design of future materials for biomedical applications but also for materials science. Functionalization of the nanocapsules was demonstrated with fluorescent labels, which can be attached to the pendant phosphoester either within the cross-linker, exploiting the versatility of the phosphorus chemistry, or via coupling to the capsules’ surface.

Carbohydrate nanocarriers in biomedical applications: functionalization and construction

“…152 Sucrose was functionalized with azide groups under Mitsunobu conditions ( Table 2, entry 5). 154 The TEM and SEM images of the obtained capsules can be seen in Fig. 12, allowing loading of the nanocarriers with hydrophobic molecules.…”

Synthesis of amide-functionalized cellulose esters by olefin cross-metathesis

“…cellulose derivatives) with terminally olefinic side-chain react with different CM partners such as acrylic acid and its esters. With the help of this chemistry, we (Dong & Edgar, 2015;Meng et al, 2014a,b) and others (Malzahn et al, 2014) have been able to introduce a variety of functional groups onto polysaccharide backbone in a mild, modular and efficient manner. In the current study, we examined the feasibility of using acrylamides as CM partners to obtain cellulose esters bearing amide functionalities, by the reaction scheme illustrated by Fig.…”

“…acrylamide) (Choi et al, 2001). Olefin CM chemistry has been adopted by the Edgar (Meng, Matson, & Edgar, 2014a;Meng, Matson, & Edgar, 2014b) and other groups (Joly, Granet, & Krausz, 2005;Malzahn et al, 2014) for polysaccharide modification towards discrete or cross-linked products. In our previous studies, cellulose esters with side-chain functionalities of carboxylic acid and a variety of carboxylate esters were synthesized by CM between -unsaturated cellulose esters (e.g.…”

Poly(phosphonate)-mediated Horner–Wadsworth–Emmons reactions

“…27,28,[35][36][37][38] Tailoring these properties allowed us to enhance the HWE reaction and its workup procedure in several model reactions. 27,28,[35][36][37][38] Tailoring these properties allowed us to enhance the HWE reaction and its workup procedure in several model reactions.…”