Novel BODIPY-Based Photobase Generators for Photoinduced Polymerization

Shupei Yu, Ojasvita Reddy, Alperen Abaci, Yongling Ai, Yanmei Li, Hao Chen, Murat Guvendiren, Kevin D. Belfield, Yuanwei Zhang

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

Photobase generators (PBGs) are compounds that utilize light-sensitive chemical-protecting groups to offer spatiotemporal control of releasing organic bases upon targeted light irradiation. PBGs can be implemented as an external control to initiate anionic polymerizations such as thiol-ene Michael addition reactions. However, there are limitations for common PBGs, including a short absorption wavelength and weak base release that lead to poor efficiency in photopolymerization. Therefore, there is a great need for visible-light-triggered PBGs that are capable of releasing strong bases efficiently. Here, we report two novel BODIPY-based visible-light-sensitive PBGs for light-induced activation of the thiol-ene Michael “click” reaction and polymerization. These PBGs were designed by connecting the BODIPY-based light-sensitive protecting group with tetramethylguanidine (TMG), a strong base. Moreover, we exploited the heavy atom effect to increase the efficiency of releasing TMG and the polymerization rate. These BODIPY-based PBGs exhibit extraordinary activity toward thiol-ene Michael addition-based polymerization, and they can be used in surface coating and polymer network formation of different thiol and vinyl monomers.

Original languageEnglish (US)
Pages (from-to)45281-45289
Number of pages9
JournalACS Applied Materials and Interfaces
Volume15
Issue number38
DOIs
StatePublished - Sep 27 2023

All Science Journal Classification (ASJC) codes

  • General Materials Science

Keywords

  • BODIPY
  • LED light
  • photobase generator
  • photopolymerization
  • thiol−ene Michael reaction

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