Coumarin‐4‐ylmethyl‐ and p‐hydroxyphenacyl‐based photoacid generators with high solubility in aqueous media: synthesis, stability and photolysis
- (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.
Verfasserangaben: | Karishma K. Adatia, Thomas Halbritter, Matiss Reinfelds, Andre Michele, Michael Tran, Sabine Laschat, Alexander HeckelORCiDGND, Günter E. M. Tovar, Alexander Southan |
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URN: | urn:nbn:de:hebis:30:3-565054 |
DOI: | https://doi.org/10.1002/cptc.201900258 |
ISSN: | 2367-0932 |
Titel des übergeordneten Werkes (Deutsch): | ChemPhotoChem |
Verlag: | Wiley-VCH GmbH |
Verlagsort: | Weinheim |
Dokumentart: | Wissenschaftlicher Artikel |
Sprache: | Englisch |
Datum der Veröffentlichung (online): | 16.12.2019 |
Datum der Erstveröffentlichung: | 16.12.2019 |
Veröffentlichende Institution: | Universitätsbibliothek Johann Christian Senckenberg |
Datum der Freischaltung: | 29.10.2020 |
Freies Schlagwort / Tag: | coumarin-4-ylmethyl; p-hydroxyphenacyl; photoacid generator; photolysis; stability; water solubility |
Jahrgang: | 4.2020 |
Ausgabe / Heft: | 3 |
Seitenzahl: | 11 |
Erste Seite: | 207 |
Letzte Seite: | 217 |
HeBIS-PPN: | 471418595 |
Institute: | Biochemie, Chemie und Pharmazie / Biochemie und Chemie |
DDC-Klassifikation: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
Sammlungen: | Universitätspublikationen |
Lizenz (Deutsch): | Creative Commons - Namensnennung 4.0 |