Structure-Activity Relationship of Benzophenazine Derivatives for Homogeneous and Heterogenized Photooxygenation Catalysis

被引:0
作者
Body, Nathalie [1 ]
Lefebvre, Corentin [1 ]
Eeckhout, Sarah [1 ]
Leonard, Anne-Sophie [1 ]
Troian-Gautier, Ludovic [1 ,2 ]
Hermans, Sophie [1 ]
Riant, Olivier [1 ]
机构
[1] Univ Catholique Louvain UCLouvain, Inst Matiere Condensee & Nanosci IMCN, Mol Chem Mat & Catalysis MOST, Pl Louis Pasteur 1,Bte L4-01-02, B-1348 Louvain La Neuve, Belgium
[2] Wel Res Inst, Ave Pasteur 6, B-1300 Wavre, Belgium
关键词
Singlet oxygen; Substitution; Silica nanoparticles; Recyclability; Photosensitization; Energy Transfer; PHOTOSENSITIZED SINGLET OXYGEN; PHOTOPHYSICAL PROPERTIES; OPTICAL-PROPERTIES; PHOTODYNAMIC THERAPY; WATER DISINFECTION; ORGANIC POLLUTANTS; BETA-LAPACHONE; IN-VITRO; GENERATION; COMPLEX;
D O I
10.1002/chem.202400242
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Singlet oxygen is a powerful oxidant used in various applications, such as organic synthesis, medicine, and environmental remediation. Organic and inorganic photosensitizers are commonly used to generate this reactive species through energy transfer with the triplet ground state of oxygen. We describe here a series of novel benzophenazine derivatives as a promising class of photosensitizers for singlet oxygen photosensitization. In this study, we investigated the structure-activity relationship of these benzophenazine derivatives. Akin to a molecular compass, the southern fragment was first functionalized with either aromatic tertiary amines, alkyl tertiary amines, aromatic sulfur groups, alkyl sulfur groups, or cyclic ethers. Enhanced photophysical properties (in terms of triplet excited-state lifetime, absorption wavelength, triplet state energy, and O2 quenching capabilities) were obtained with cyclic ether and sulfur groups. Conversely, the presence of an amine moiety was detrimental to the photocatalysts. The western and northern fragments were also investigated and slightly undesirable to negligible changes in photophysical properties were observed. The most promising candidate was then immobilized on silica nanoparticles and its photoactivity was evaluated in the citronellol photooxidation reaction. A high NMR yield of 97 % in desired product was obtained, with only a slight decrease over several recycling runs (85 % in the fourth run). These results provide insights into the design of efficient photosensitizers for singlet oxygen generation and the development of heterogeneous systems. A new familly of benzophenazine derivatives was designed as photosensitizers for singlet oxygen generation. Extensive structure activity relationship was carried out using both experimental and theoretical approach. The most promising candidate was immobilized on silica nanoparticles and its photoactivity was evaluated in the citronellol photooxidation. image
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页数:16
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