Synthesis and Self‐Assembly of Stimuli‐Responsive Amphiphilic Dendrimers

Abstract

The synthesis of stimuli-responsive amphiphilic dendrimers consisting of two or three hydrophobic octadecyl groups linked to either a second or third generation hydrophilic polylysine dendron through disulfide linkage is reported. The polylysine dendrimers functionalized with four or eight tert-butyloxycarbonyl (Boc)-protected amino groups are characterized by 1 H NMR spectroscopy and matrix-assisted laser desorption ionization time-of-flight (MALDI-TOF) mass spectrometry. With the positively charged versions generated by removing the Boc groups, their ability to form spherical micelles that can be readily disassembled in the presence of glutathione (GSH) is demonstrated. The self-assembly behavior is monitored by scanning electron microscopy (SEM) and dynamic light scattering (DLS). The amphiphilic dendritic systems containing cleavable disulfide linkage serve as key building blocks for generating stimuli-responsive supramolecular architectures.

Epichlorohydrin-based CuAAC dendrimers with a calix[4]arene core and polar hydroxyl/oxyethyl terminal groups: synthesis, aggregation and use in catalysis

“…14,15 In the last decade, amphiphilic dendrimers, a broad series of dendrimers of asymmetric structure that includes core-shell dendrimers, Janus dendrimers, dendron-tail dendrimers as well as glycodendrimers, have attracted great attention. [16][17][18][19][20] Such structures, in addition to the inherent branched structure of dendrimers, have the ability to self-assemble to form various nanostructures, including both conventional micelles 19 and liposome-like dendrimersomes. 21 The unique chemistry of calix-and thiacalix [4]arenes, consisting of the possibility of modification of both lower and upper rims, as well as the presence of four stereoisomers, made them a convenient platform to use both as a dendrimer's core [22][23][24][25][26][27] and as dendrones.…”