Vesicles or micelles prepared from amphiphiles with azobenzene (Az) moieties and long alkyl chains have attracted much attention in drug delivery systems. To induce release behavior from smart carriersvia trans-cisphotoisomerization of theAzgroups, UV light exposure is typically used, but it can damage DNA and hardly penetrates cells. In this paper,Az-containing phospholipids without long alkyl tails were designed and synthesized; in these compounds, the end group of theAzmoiety was substituted with a -NO2and -OCH3group (abbreviatedN6andM6, respectively).N6self-assembled into H-aggregates with an interdigitated bilayered structure in water through the antiparallel orientation due to π-π interactions of theAzgroup, the attractive van der Waals forces, and the interactions and bending behavior of the phosphocholine groups. Vesicles showing visible light stimuli-responsive behavior were obtained by mixingN6andM6, and the release of encapsulated calcein was triggered by visible light.
ASJC Scopus subject areas
- Chemical Engineering(all)