Light-Induced Step-Growth Polymerization of AB-Type Photo-Monomers at Ambient Temperature

Silvana Hurrle; Anja S Goldmann; Hartmut Gliemann; Hatice Mutlu; Christopher Barner-Kowollik

doi:10.1021/acsmacrolett.7b01001

Light-Induced Step-Growth Polymerization of AB-Type Photo-Monomers at Ambient Temperature

ACS Macro Lett. 2018 Feb 20;7(2):201-207. doi: 10.1021/acsmacrolett.7b01001. Epub 2018 Jan 30.

Authors

Silvana Hurrle¹, Anja S Goldmann^{2

1}, Hartmut Gliemann³, Hatice Mutlu^{2

4}, Christopher Barner-Kowollik^{2

1

4}

Affiliations

¹ Macromolecular Architectures, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology (KIT), Engesserstraße 18, 76128 Karlsruhe, Germany.
² School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology (QUT), 2 George Street, QLD 4000, Brisbane, Australia.
³ Institut für Funktionelle Grenzflächen, Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344 Karlsruhe, Germany.
⁴ Soft Matter Synthesis Laboratory, Institut für Biologische Grenzflächen, Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany.

PMID: 35610893
DOI: 10.1021/acsmacrolett.7b01001

Abstract

We introduce two AB-type monomers able to undergo a facile catalyst-free photoinduced polycycloaddition of photocaged dienes, enabling rapid Diels-Alder ligations under UV-irradiation (λ_max = 350 nm) at ambient temperature, closely adhering to Carother's equation established by a careful kinetic study (17800 g mol^-1 < M_w < 24700 g mol^-1). The resulting macromolecules were in-depth analyzed via size exclusion chromatography (SEC) and nuclear magnetic resonance (NMR) spectroscopy. Additionally, SEC hyphenated to high resolution-electrospray ionization-mass spectrometry (HR-ESI-MS) enabled the careful mapping of the end group structure of the generated polymers. Furthermore, we demonstrate that both monomer systems can be readily copolymerized. The study thus demonstrates that Diels-Alder ligation resting upon photocaged dienes is a powerful tool for accessing step-growth polymers.