Article: Synthesis and photophysical properties of photostable 1,8-naphthalimide dyes incorporating benzotriazole-based UV absorbers
RSC advances. 2022 June 13, v. 12, no. 27
2022
Abstract: We developed a series of blue-emitting 1,8-naphthalimide dyes covalently attached to 2-(2-hydroxyphenyl)-2H-benzotriazoles that retard photodegradation of the fluorophore. The dyes displayed weaker fluorescence emissions than the parent 1.8-naphthalimide. ...
| Abstract | We developed a series of blue-emitting 1,8-naphthalimide dyes covalently attached to 2-(2-hydroxyphenyl)-2H-benzotriazoles that retard photodegradation of the fluorophore. The dyes displayed weaker fluorescence emissions than the parent 1.8-naphthalimide. Quantum chemical calculations suggested that the decreased fluorescence was caused by the nonradiative deactivation promoted through the excited state intramolecular proton transfer (ESIPT) in benzotriazole components. The dyes' phosphorescences in a degassed solution at 77 K were more efficient than that of the parent 1.8-naphthalimide, indicating a possible deactivation pathway through intersystem crossing. PMMA films doped with these dyes showed higher resistance against photoaging than the film doped with an equimolar mixture of constituent 1.8-naphthalimide and the benzotriazole derivatives. Thus, the covalently linked benzotriazole units slow fluorophore degradation not only by preferential absorption of harmful UV light, which is found in the film with a simple mixture of two components, but also by the nonradiative deactivation involved in benzotriazole units. |
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| Keywords | absorption ; chemical bonding ; fluorescence ; fluorescent dyes ; photoaging ; photolysis ; quantum mechanics ; triazoles ; ultraviolet radiation |
| Language | English |
| Dates of publication | 2022-0613 |
| Size | p. 17350-17361. |
| Publishing place | The Royal Society of Chemistry |
| Document type | Article |
| ISSN | 2046-2069 |
| DOI | 10.1039/d2ra02028a |
| Database | NAL-Catalogue (AGRICOLA) |
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