Degradable fluorescent single-chain nanoparticles based on metathesis polymers

Janin T Offenloch; Johannes Willenbacher; Pavleta Tzvetkova; Carolin Heiler; Hatice Mutlu; Christopher Barner-Kowollik

doi:10.1039/c6cc08554g

Degradable fluorescent single-chain nanoparticles based on metathesis polymers

Chem Commun (Camb). 2017 Jan 5;53(4):775-778. doi: 10.1039/c6cc08554g.

Authors

Janin T Offenloch¹, Johannes Willenbacher¹, Pavleta Tzvetkova², Carolin Heiler¹, Hatice Mutlu¹, Christopher Barner-Kowollik³

Affiliations

¹ Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology (KIT), Engesserstraße 18, 76128 Karlsruhe, Germany and Soft Matter Synthesis Laboratory, Institut für Biologische Grenzflächen, Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344 Karlsruhe, Germany. hatice.mutlu@kit.edu christopher.barner-kowollik@kit.edu.
² Institute of Organic Chemistry and Institute for Biological Interfaces 4 - Magnetic Resonance, Karlsruhe Institute for Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany.
³ Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology (KIT), Engesserstraße 18, 76128 Karlsruhe, Germany and Soft Matter Synthesis Laboratory, Institut für Biologische Grenzflächen, Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344 Karlsruhe, Germany. hatice.mutlu@kit.edu christopher.barner-kowollik@kit.edu and School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology (QUT), 2 George Street, QLD 4000, Brisbane, Australia. christopher.barnerkowollik@qut.edu.au.

PMID: 27999836
DOI: 10.1039/c6cc08554g

Abstract

We introduce the facile synthesis of fluorescent single-chain nanoparticles (SCNPs) based on chain-shattering acyclic diene metathesis (ADMET) polymers featuring self-immolative azobenzene motifs. An electrophilic alkoxyetherification is utilized to introduce the photoreactive moieties required for the subsequent chain collapse via UV-induced nitrile imine-mediated tetrazole-ene cycloaddition (NITEC).