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.