dc.contributor |
Háskóli Íslands |
dc.contributor |
University of Iceland |
dc.contributor.author |
Adatia, Karishma K. |
dc.contributor.author |
Halbritter, Thomas |
dc.contributor.author |
Reinfelds, Matiss |
dc.contributor.author |
Michele, Andre |
dc.contributor.author |
Tran, Michael |
dc.contributor.author |
Laschat, Sabine |
dc.contributor.author |
Heckel, Alexander |
dc.contributor.author |
Tovar, Günter E. M. |
dc.contributor.author |
Southan, Alexander |
dc.date.accessioned |
2021-01-25T13:57:07Z |
dc.date.available |
2021-01-25T13:57:07Z |
dc.date.issued |
2020-01-16 |
dc.identifier.citation |
K. K. Adatia, T. Halbritter, M. Reinfelds, A. Michele, M. Tran, S. Laschat, A. Heckel, G. E. M. Tovar, A. Southan, ChemPhotoChem 2020, 4, 207. |
dc.identifier.issn |
2367-0932 |
dc.identifier.uri |
https://hdl.handle.net/20.500.11815/2405 |
dc.description |
Publisher's version (útgefin grein) |
dc.description.abstract |
(Coumarin-4-yl)methyl (c4m) and p-hydroxyphenacyl (pHP)-based compounds are well known for their highly efficient photoreactions, but often show limited solubility in aqueous media. To circumvent this, we synthesized and characterized the two new c4m and pHP-based photoacid generators (PAGs), 7-[bis(carboxymethyl)amino]-4-(acetoxymethyl)coumarin (c4m-ac) and p-hydroxyphenacyl-2,5,8,11-tetraoxatridecan-13-oate (pHP-t), and determined their solubilities, stabilities and photolysis in aqueous media. The two compounds showed high solubilities in water of 2.77 mmol L−1±0.07 mmol L−1 (c4m-ac) and 124.66 mmol L−1±2.1 mmol L−1 (pHP-t). In basic conditions at pH 9, solubility increased for c4m-ac to 646.46 mmol L−1±0.63 mmol L−1, for pHP-t it decreased to 34.68 mmol L−1±0.62 mmol L−1. Photochemical properties of the two PAGs, such as the absorption maxima, the maximum molar absorption coefficients and the quantum yields, were found to be strongly pH-dependent. Both PAGs showed high stabilities s24h ≥95 % in water for 24 h, but decreasing stability with increasing pH value due to hydrolysis. The present study contributes to a clearer insight into the synthesis, solubilities, stabilities, and photolysis of c4m and pHP-based PAGs for further photochemical applications when high PAG concentrations are required, such as in polymeric foaming. |
dc.description.sponsorship |
K. A. gratefully acknowledges financial support by the Evonik Foundation. We thank the University of Stuttgart and the Fraunhofer‐Gesellschaft for provision of infrastructure and gratefully acknowledge generous financial support by the Carl Zeiss Foundation and the University of Stuttgart within the . The contribution by A.H. was made possible by SFB 902 and GRK 1986 of the Deutsche Forschungsgemeinschaft. Projekthaus NanoBioMater |
dc.format.extent |
207-217 |
dc.language.iso |
en |
dc.publisher |
Wiley |
dc.relation.ispartofseries |
ChemPhotoChem;4(3) |
dc.rights |
info:eu-repo/semantics/openAccess |
dc.subject |
Coumarin-4-ylmethyl |
dc.subject |
p-hydroxyphenacyl |
dc.subject |
Photoacid generators |
dc.subject |
Photolysis |
dc.subject |
Stability |
dc.subject |
Water solubility |
dc.subject |
Efnafræði |
dc.subject |
Efnasamsetning |
dc.title |
Coumarin‐4‐ylmethyl‐ and p ‐Hydroxyphenacyl‐Based Photoacid Generators with High Solubility in Aqueous Media: Synthesis, Stability and Photolysis |
dc.type |
info:eu-repo/semantics/article |
dcterms.license |
This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
dc.description.version |
Peer Reviewed |
dc.identifier.journal |
ChemPhotoChem |
dc.identifier.doi |
10.1002/cptc.201900258 |
dc.relation.url |
https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/cptc.201900258 |
dc.contributor.department |
Raunvísindadeild (HÍ) |
dc.contributor.department |
Faculty of Physical Sciences (UI) |
dc.contributor.school |
Verkfræði- og náttúruvísindasvið (HÍ) |
dc.contributor.school |
School of Engineering and Natural Sciences (UI) |