Tetraacylgermanes: Highly Efficient Photoinitiators for Visible-Light-Induced Free-Radical Polymerization

Judith Radebner; Anna Eibel; Mario Leypold; Christian Gorsche; Lukas Schuh; Roland Fischer; Ana Torvisco; Dmytro Neshchadin; Roman Geier; Norbert Moszner; Robert Liska; Georg Gescheidt; Michael Haas; Harald Stüger

doi:10.1002/anie.201611686

Tetraacylgermanes: Highly Efficient Photoinitiators for Visible-Light-Induced Free-Radical Polymerization

Judith Radebner, Anna Eibel, Mario Leypold, Christian Gorsche, Lukas Schuh, Roland Fischer, Ana Torvisco, Dmytro Neshchadin, Roman Geier, Norbert Moszner, Robert Liska, Georg Gescheidt, Michael Haas, Harald Stüger

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

Abstract

In this contribution a convenient synthetic method to obtain tetraacylgermanes Ge[C(O)R]4 (R=mesityl (1 a), phenyl (1 b)), a previously unknown class of highly efficient Ge-based photoinitiators, is described. Tetraacylgermanes are easily accessible via a one-pot synthetic protocol in >85 % yield, as confirmed by NMR spectroscopy, mass spectrometry, and X-ray crystallography. The efficiency of 1 a,b as photoinitiators is demonstrated in photobleaching (UV/Vis), time-resolved EPR (CIDEP), and NMR/CIDNP investigations as well as by photo-DSC studies. Remarkably, the tetraacylgermanes exceed the performance of currently known long-wavelength visible-light photoinitiators for free-radical polymerization.

Original language	English
Pages (from-to)	3103-3107
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	11
DOIs	https://doi.org/10.1002/anie.201611686
Publication status	Published - 2017

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Radebner, J., Eibel, A., Leypold, M., Gorsche, C., Schuh, L., Fischer, R., Torvisco, A., Neshchadin, D., Geier, R., Moszner, N., Liska, R., Gescheidt, G., Haas, M., & Stüger, H. (2017). Tetraacylgermanes: Highly Efficient Photoinitiators for Visible-Light-Induced Free-Radical Polymerization. Angewandte Chemie - International Edition , 56(11), 3103-3107. https://doi.org/10.1002/anie.201611686

Radebner, J, Eibel, A, Leypold, M, Gorsche, C, Schuh, L, Fischer, R , Torvisco, A , Neshchadin, D, Geier, R, Moszner, N, Liska, R, Gescheidt, G , Haas, M & Stüger, H 2017, 'Tetraacylgermanes: Highly Efficient Photoinitiators for Visible-Light-Induced Free-Radical Polymerization', Angewandte Chemie - International Edition , vol. 56, no. 11, pp. 3103-3107. https://doi.org/10.1002/anie.201611686

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title = "Tetraacylgermanes: Highly Efficient Photoinitiators for Visible-Light-Induced Free-Radical Polymerization",

abstract = "In this contribution a convenient synthetic method to obtain tetraacylgermanes Ge[C(O)R]4 (R=mesityl (1 a), phenyl (1 b)), a previously unknown class of highly efficient Ge-based photoinitiators, is described. Tetraacylgermanes are easily accessible via a one-pot synthetic protocol in >85 % yield, as confirmed by NMR spectroscopy, mass spectrometry, and X-ray crystallography. The efficiency of 1 a,b as photoinitiators is demonstrated in photobleaching (UV/Vis), time-resolved EPR (CIDEP), and NMR/CIDNP investigations as well as by photo-DSC studies. Remarkably, the tetraacylgermanes exceed the performance of currently known long-wavelength visible-light photoinitiators for free-radical polymerization.",

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author = "Judith Radebner and Anna Eibel and Mario Leypold and Christian Gorsche and Lukas Schuh and Roland Fischer and Ana Torvisco and Dmytro Neshchadin and Roman Geier and Norbert Moszner and Robert Liska and Georg Gescheidt and Michael Haas and Harald St{\"u}ger",

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doi = "10.1002/anie.201611686",

language = "English",

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T1 - Tetraacylgermanes: Highly Efficient Photoinitiators for Visible-Light-Induced Free-Radical Polymerization

AU - Radebner, Judith

AU - Eibel, Anna

AU - Leypold, Mario

AU - Gorsche, Christian

AU - Schuh, Lukas

AU - Fischer, Roland

AU - Torvisco, Ana

AU - Neshchadin, Dmytro

AU - Geier, Roman

AU - Moszner, Norbert

AU - Liska, Robert

AU - Gescheidt, Georg

AU - Haas, Michael

AU - Stüger, Harald

PY - 2017

Y1 - 2017

N2 - In this contribution a convenient synthetic method to obtain tetraacylgermanes Ge[C(O)R]4 (R=mesityl (1 a), phenyl (1 b)), a previously unknown class of highly efficient Ge-based photoinitiators, is described. Tetraacylgermanes are easily accessible via a one-pot synthetic protocol in >85 % yield, as confirmed by NMR spectroscopy, mass spectrometry, and X-ray crystallography. The efficiency of 1 a,b as photoinitiators is demonstrated in photobleaching (UV/Vis), time-resolved EPR (CIDEP), and NMR/CIDNP investigations as well as by photo-DSC studies. Remarkably, the tetraacylgermanes exceed the performance of currently known long-wavelength visible-light photoinitiators for free-radical polymerization.

AB - In this contribution a convenient synthetic method to obtain tetraacylgermanes Ge[C(O)R]4 (R=mesityl (1 a), phenyl (1 b)), a previously unknown class of highly efficient Ge-based photoinitiators, is described. Tetraacylgermanes are easily accessible via a one-pot synthetic protocol in >85 % yield, as confirmed by NMR spectroscopy, mass spectrometry, and X-ray crystallography. The efficiency of 1 a,b as photoinitiators is demonstrated in photobleaching (UV/Vis), time-resolved EPR (CIDEP), and NMR/CIDNP investigations as well as by photo-DSC studies. Remarkably, the tetraacylgermanes exceed the performance of currently known long-wavelength visible-light photoinitiators for free-radical polymerization.

KW - acylgermanes

KW - photochemistry

KW - photoinitiators

KW - radical polymerization

KW - reaction mechanisms

U2 - 10.1002/anie.201611686

DO - 10.1002/anie.201611686

M3 - Article

C2 - 28156043

SN - 1521-3773

VL - 56

SP - 3103

EP - 3107

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 11

ER -

Tetraacylgermanes: Highly Efficient Photoinitiators for Visible-Light-Induced Free-Radical Polymerization

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