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

Publikation: Beitrag in einer Fachzeitschrift › Artikel › Begutachtung

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.

Originalsprache	englisch
Seiten (von - bis)	3103-3107
Seitenumfang	5
Fachzeitschrift	Angewandte Chemie - International Edition
Jahrgang	56
Ausgabenummer	11
DOIs	https://doi.org/10.1002/anie.201611686
Publikationsstatus	Veröffentlicht - 2017

Schlagwörter

acylgermanes
photochemistry
photoinitiators
radical polymerization
reaction mechanisms

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10.1002/anie.201611686

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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 , Jg. 56, Nr. 11, S. 3103-3107. https://doi.org/10.1002/anie.201611686

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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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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

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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ER -

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

Abstract

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