Exploring Aromatic S-Thioformates as Photoinitiators

Paul Rieger; Sabrina Pueschmann; Michael Haas; Max Schmallegger; Gema del Carmen Guedes de la Cruz; Thomas Grießer

doi:10.3390/polym15071647

Exploring Aromatic S-Thioformates as Photoinitiators

Paul Rieger, Sabrina Pueschmann, Michael Haas, Max Schmallegger, Gema del Carmen Guedes de la Cruz, Thomas Grießer

Chair of Chemistry of Polymeric Materials (231)

Technische Universität Graz

Research output: Contribution to journal › Article › Research › peer-review

Abstract

Thiyl radicals were generated from aromatic S-thioformates by photolysis. The corresponding photo-initiated decarbonylation allows initiating polymerization reactions in both acrylate- and thiol-acrylate-based resin systems. Compared to aromatic thiols, the introduction of the photolabile formyl group prevents undesired reactions with acrylate monomers allowing photoinitiators (PIs) with constant reactivity over storage. To demonstrate the potential of S-thioformates as PIs, the bifunctional molecule S,S′-(thiobis(4,1-phenylene))dimethanethioate (2b) was synthesized, providing reactivity under visible light excitation. Consequently, acrylate-based formulations could successfully be processed by digital light processing (DLP)-based stereolithography at 405 nm in high resolution.

Original language	English
Article number	1647
Number of pages	8
Journal	Polymers
Volume	15.2023
Issue number	7
DOIs	https://doi.org/10.3390/polym15071647
Publication status	Published - Apr 2023

Bibliographical note

Keywords

photochemistry
photoinitiator
thiol-ene

Access to Document

10.3390/polym15071647

Cite this

@article{6ad3a74de46348b590d55ade91ac9844,

title = "Exploring Aromatic S-Thioformates as Photoinitiators",

abstract = "Thiyl radicals were generated from aromatic S-thioformates by photolysis. The corresponding photo-initiated decarbonylation allows initiating polymerization reactions in both acrylate- and thiol-acrylate-based resin systems. Compared to aromatic thiols, the introduction of the photolabile formyl group prevents undesired reactions with acrylate monomers allowing photoinitiators (PIs) with constant reactivity over storage. To demonstrate the potential of S-thioformates as PIs, the bifunctional molecule S,S′-(thiobis(4,1-phenylene))dimethanethioate (2b) was synthesized, providing reactivity under visible light excitation. Consequently, acrylate-based formulations could successfully be processed by digital light processing (DLP)-based stereolithography at 405 nm in high resolution.",

keywords = "photochemistry, photoinitiator, thiol-ene",

author = "Paul Rieger and Sabrina Pueschmann and Michael Haas and Max Schmallegger and {Guedes de la Cruz}, {Gema del Carmen} and Thomas Grie{\ss}er",

note = "Publisher Copyright: {\textcopyright} 2023 by the authors.",

year = "2023",

month = apr,

doi = "10.3390/polym15071647",

language = "English",

volume = "15.2023",

journal = "Polymers",

issn = "2073-4360",

publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

number = "7",

}

TY - JOUR

T1 - Exploring Aromatic S-Thioformates as Photoinitiators

AU - Rieger, Paul

AU - Pueschmann, Sabrina

AU - Haas, Michael

AU - Schmallegger, Max

AU - Guedes de la Cruz, Gema del Carmen

AU - Grießer, Thomas

PY - 2023/4

Y1 - 2023/4

N2 - Thiyl radicals were generated from aromatic S-thioformates by photolysis. The corresponding photo-initiated decarbonylation allows initiating polymerization reactions in both acrylate- and thiol-acrylate-based resin systems. Compared to aromatic thiols, the introduction of the photolabile formyl group prevents undesired reactions with acrylate monomers allowing photoinitiators (PIs) with constant reactivity over storage. To demonstrate the potential of S-thioformates as PIs, the bifunctional molecule S,S′-(thiobis(4,1-phenylene))dimethanethioate (2b) was synthesized, providing reactivity under visible light excitation. Consequently, acrylate-based formulations could successfully be processed by digital light processing (DLP)-based stereolithography at 405 nm in high resolution.

AB - Thiyl radicals were generated from aromatic S-thioformates by photolysis. The corresponding photo-initiated decarbonylation allows initiating polymerization reactions in both acrylate- and thiol-acrylate-based resin systems. Compared to aromatic thiols, the introduction of the photolabile formyl group prevents undesired reactions with acrylate monomers allowing photoinitiators (PIs) with constant reactivity over storage. To demonstrate the potential of S-thioformates as PIs, the bifunctional molecule S,S′-(thiobis(4,1-phenylene))dimethanethioate (2b) was synthesized, providing reactivity under visible light excitation. Consequently, acrylate-based formulations could successfully be processed by digital light processing (DLP)-based stereolithography at 405 nm in high resolution.

KW - photochemistry

KW - photoinitiator

KW - thiol-ene

UR - http://www.scopus.com/inward/record.url?scp=85152860854&partnerID=8YFLogxK

U2 - 10.3390/polym15071647

DO - 10.3390/polym15071647

M3 - Article

AN - SCOPUS:85152860854

SN - 2073-4360

VL - 15.2023

JO - Polymers

JF - Polymers

IS - 7

M1 - 1647

ER -

Exploring Aromatic S-Thioformates as Photoinitiators

Abstract

Bibliographical note

Keywords

Access to Document

Other files and links

Cite this