Novel BODIPY-Based Photobase Generators for Photoinduced Polymerization

Document Type

Article

Publication Date

9-27-2023

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.

Identifier

85174642039 (Scopus)

Publication Title

ACS Applied Materials and Interfaces

External Full Text Location

https://doi.org/10.1021/acsami.3c09326

e-ISSN

19448252

ISSN

19448244

PubMed ID

37708358

First Page

45281

Last Page

45289

Issue

38

Volume

15

Grant

2044479

Fund Ref

National Science Foundation

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