Motyka Radosław, Nastula Klaudia, Pander Piotr, Honisz Damian, Tomczyk Mateusz, Erfurt Karol, Blacha-Grzechnik Agata
Faculty of Chemistry, Silesian University of Technology, Strzody 9, 44-100 Gliwice, Poland.
Centre of Polymer and Carbon Materials, Polish Academy of Sciences, Curie-Sklodowskiej 34, 41-819 Zabrze, Poland.
Materials (Basel). 2023 Mar 24;16(7):2605. doi: 10.3390/ma16072605.
Fullerenes have been long investigated for application as singlet oxygen sources. Even though they possess high photosensitizing efficiency, their practical use is still limited, mostly because of insufficient absorption of visible and/or near-infrared light. This limitation can be overcome by introducing organic chromophores that absorb longer-wavelength light, either by covalent attachment to C or by its encapsulation in a polymeric matrix. In this work, we investigated the photosensitizing properties of the C molecule functionalized with organic units comprising thiophene or selenophene rings. The chemical structures of the synthesized dyads were characterized by nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry. The influence of the S/Se atoms and vinyl linkage between the organic unit and C on the absorptive and emissive properties of the dyads was investigated and correlated with their photosensitizing activity. For the latter, we used a standard chemical singlet oxygen trap. A selected dyad CThSe was also applied as a source of singlet oxygen in a model photocatalyzed synthesis of the fine chemical juglone from 1,5-dihydroxynapthalene.
富勒烯作为单线态氧源的应用已被长期研究。尽管它们具有高光敏效率，但其实际应用仍然有限，主要是因为对可见光和/或近红外光的吸收不足。通过引入吸收更长波长光的有机发色团可以克服这一限制，这些发色团可以通过与碳共价连接或封装在聚合物基质中实现。在这项工作中，我们研究了用包含噻吩或硒吩环的有机单元功能化的碳分子的光敏性质。合成的二元化合物的化学结构通过核磁共振（NMR）光谱和质谱进行了表征。研究了硫/硒原子以及有机单元与碳之间的乙烯基连接对二元化合物吸收和发射性质的影响，并将其与它们的光敏活性相关联。对于后者，我们使用了标准的化学单线态氧捕获剂。在由1,5 - 二羟基萘光催化合成精细化学品胡桃醌的模型反应中，还将选定的二元化合物CThSe用作单线态氧源。
