Tetraacylstannanes as Long-Wavelength Visible-Light Photoinitiators with Intriguing Low Toxicity

Judith Radebner; Anna Eibel; Mario Leypold; Nina Jungwirth; Thomas Pickl; Ana Torvisco; Roland Fischer; Urs Karl Fischer; Norbert Moszner; Georg Gescheidt; Harald Stueger; Michael Haas

doi:10.1002/chem.201801622

Tetraacylstannanes as Long-Wavelength Visible-Light Photoinitiators with Intriguing Low Toxicity

Judith Radebner^*, Anna Eibel, Mario Leypold, Nina Jungwirth, Thomas Pickl, Ana Torvisco, Roland Fischer, Urs Karl Fischer, Norbert Moszner, Georg Gescheidt, Harald Stueger, Michael Haas

^*Corresponding author for this work

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

Abstract

The first tetraacylstannanes Sn[(CO)R]₄ (R=2,4,6-trimethylphenyl (1 a) and 2,6-dimethylphenyl (1 b)), a class of highly efficient Sn-based photoinitiators, were synthesized. The formation of these derivatives was confirmed by NMR spectroscopy, mass spectrometry, and X-ray crystallography. The UV/Vis absorption spectra of 1 a, b reveal a significant redshift of the longest wavelength absorption compared to the corresponding germanium compounds. In contrast to the known toxicity of organotin derivatives, the AMES test and cytotoxicity studies reveal intriguing low toxicity. The excellent performance of 1 as photoinitiators is demonstrated by photobleaching (UV/Vis) and NMR/CIDNP investigations, as well as photo-DSC studies.

Original language	English
Pages (from-to)	8281-8285
Number of pages	5
Journal	Chemistry - a European Journal
Volume	24
Issue number	33
DOIs	https://doi.org/10.1002/chem.201801622
Publication status	Published - 12 Jun 2018

Keywords

acylstannanes
organostannanes
photochemistry
photoinitiators
radical polymerization

ASJC Scopus subject areas

General Chemistry

Access to Document

10.1002/chem.201801622

Cite this

@article{18bafec7ef514be2a8195b1377382354,

title = "Tetraacylstannanes as Long-Wavelength Visible-Light Photoinitiators with Intriguing Low Toxicity",

abstract = "The first tetraacylstannanes Sn[(CO)R]4 (R=2,4,6-trimethylphenyl (1 a) and 2,6-dimethylphenyl (1 b)), a class of highly efficient Sn-based photoinitiators, were synthesized. The formation of these derivatives was confirmed by NMR spectroscopy, mass spectrometry, and X-ray crystallography. The UV/Vis absorption spectra of 1 a, b reveal a significant redshift of the longest wavelength absorption compared to the corresponding germanium compounds. In contrast to the known toxicity of organotin derivatives, the AMES test and cytotoxicity studies reveal intriguing low toxicity. The excellent performance of 1 as photoinitiators is demonstrated by photobleaching (UV/Vis) and NMR/CIDNP investigations, as well as photo-DSC studies.",

keywords = "acylstannanes, organostannanes, photochemistry, photoinitiators, radical polymerization",

author = "Judith Radebner and Anna Eibel and Mario Leypold and Nina Jungwirth and Thomas Pickl and Ana Torvisco and Roland Fischer and Fischer, {Urs Karl} and Norbert Moszner and Georg Gescheidt and Harald Stueger and Michael Haas",

year = "2018",

month = jun,

day = "12",

doi = "10.1002/chem.201801622",

language = "English",

volume = "24",

pages = "8281--8285",

journal = "Chemistry - a European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH ",

number = "33",

}

TY - JOUR

T1 - Tetraacylstannanes as Long-Wavelength Visible-Light Photoinitiators with Intriguing Low Toxicity

AU - Radebner, Judith

AU - Eibel, Anna

AU - Leypold, Mario

AU - Jungwirth, Nina

AU - Pickl, Thomas

AU - Torvisco, Ana

AU - Fischer, Roland

AU - Fischer, Urs Karl

AU - Moszner, Norbert

AU - Gescheidt, Georg

AU - Stueger, Harald

AU - Haas, Michael

PY - 2018/6/12

Y1 - 2018/6/12

N2 - The first tetraacylstannanes Sn[(CO)R]4 (R=2,4,6-trimethylphenyl (1 a) and 2,6-dimethylphenyl (1 b)), a class of highly efficient Sn-based photoinitiators, were synthesized. The formation of these derivatives was confirmed by NMR spectroscopy, mass spectrometry, and X-ray crystallography. The UV/Vis absorption spectra of 1 a, b reveal a significant redshift of the longest wavelength absorption compared to the corresponding germanium compounds. In contrast to the known toxicity of organotin derivatives, the AMES test and cytotoxicity studies reveal intriguing low toxicity. The excellent performance of 1 as photoinitiators is demonstrated by photobleaching (UV/Vis) and NMR/CIDNP investigations, as well as photo-DSC studies.

AB - The first tetraacylstannanes Sn[(CO)R]4 (R=2,4,6-trimethylphenyl (1 a) and 2,6-dimethylphenyl (1 b)), a class of highly efficient Sn-based photoinitiators, were synthesized. The formation of these derivatives was confirmed by NMR spectroscopy, mass spectrometry, and X-ray crystallography. The UV/Vis absorption spectra of 1 a, b reveal a significant redshift of the longest wavelength absorption compared to the corresponding germanium compounds. In contrast to the known toxicity of organotin derivatives, the AMES test and cytotoxicity studies reveal intriguing low toxicity. The excellent performance of 1 as photoinitiators is demonstrated by photobleaching (UV/Vis) and NMR/CIDNP investigations, as well as photo-DSC studies.

KW - acylstannanes

KW - organostannanes

KW - photochemistry

KW - photoinitiators

KW - radical polymerization

UR - http://www.scopus.com/inward/record.url?scp=85047763747&partnerID=8YFLogxK

U2 - 10.1002/chem.201801622

DO - 10.1002/chem.201801622

M3 - Article

AN - SCOPUS:85047763747

SN - 0947-6539

VL - 24

SP - 8281

EP - 8285

JO - Chemistry - a European Journal

JF - Chemistry - a European Journal

IS - 33

ER -

Tetraacylstannanes as Long-Wavelength Visible-Light Photoinitiators with Intriguing Low Toxicity

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this