Related Experiment Video
Updated: Feb 13, 2026

The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry
Published on: August 25, 2016
Reversible Nanogate System for Mesoporous Silica Nanoparticles Based on Diels-Alder Adducts
Rafael R Castillo1,2, David Hernández-Escobar1,3, Sergio Gómez-Graña1
1Dpto. Química en Ciencias Farmacéuticas, Facultad de Farmacia, Universidad Complutense de Madrid, Plaza Ramón y Cajal s/n, 28040, Madrid, Spain.
Abstract:
The implementation of nanoparticles as nanomedicines requires sophisticated surface modifications to reduce the immune response and enhance recognition abilities. Mesoporous silica nanoparticles present extraordinary host-guest abilities and facile surface functionalization. These two factors make them ideal candidates for the development of novel drug-delivery systems, at the expense of increasing structural complexity. With this idea in mind, a system composed of triggerable and tunable silica nanoparticles was developed for application as drug-delivery nanocarriers. Diels-Alder cycloaddition adducts were chosen as thermal-responsive units that permitted the binding of gold nanocaps able to block the pores and allow the incorporation of targeting fragments. The capping efficiency was tested under different thermal conditions to give outstanding efficiencies within the physiological range and mild temperatures, as well as enhanced release under pulsing heating cycles, which showed the best release profiles.
Related Concept Videos
Diels–Alder vs Retro-Diels–Alder Reaction: Thermodynamic Factors
Diels–Alder Reaction: Characteristics of Dienes
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable,...
Diels–Alder Reaction: Characteristics of Dienophiles
Characteristics of Dienophiles
Generally, the best dienophiles are alkenes containing electron-withdrawing substituents such as carbonyl, nitrile, and nitro groups. The feasibility of a Diels–Alder reaction depends...
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

