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Modifying the meso-phenyl with electron donating amino groups strongly enhances BODIPY's ability as good singlet oxygen photosensitizer
Dyes and Pigments ( IF 4.5 ) Pub Date : 2017-10-16 , DOI: 10.1016/j.dyepig.2017.10.018
Wenbin Hu , Xian-Fu Zhang , Xulin Lu , Shuai Lan , Dandan Tian , Tingting Li , Liangxia Wang , Siwen Zhao , Mingna Feng , Jing Zhang

We synthesized three 1,3,5,7-tetramethyl-BODIPY (1a, 2a, 3a) and three 3,5-dimethyl-BODIPY (1b, 2b, 3b) photosensitizers, in which the meso position was modified by different para-aminophenyl groups. The singlet oxygen generation and photophysical properties of the BODIPYs were studied by UV-vis absorption spectra, fluorescence emission spectra methods in various solvents. It was found that these BODIPY derivatives were environment-sensitive and fluorescent photosensitizers, which show high efficiency for generating singlet oxygen in medium polar environments but little photoactivity in polar and non polar solvents. In the mean time, they are highly fluorescent in nonpolar solvents but much less emissive in polar solvents, ICT emission occurs in medium polar solvents and correlated with singlet oxygen formation efficiency. The results are explained by PCT (photoinduced charge transfer) mechanism. The presence of the methyl groups at 1 and 7 positions disables the rotation of the phenyl ring, and therefore, the corresponding BODIPY 1a, 2a, and 3a were characterized by significant higher singlet oxygen generation efficiency and fluorescence quantum yield than that of BODIPY 1b, 2b, and 3b.



中文翻译:

用给电子氨基修饰内消旋苯基可大大增强BODIPY作为单线态氧光敏剂的能力

我们合成了三种1,3,5,7-四甲基-BODIPY(1a2a3a)和三种3,5-二甲基-BODIPY(1b2b3b)光敏剂,其中内消旋位置被不同的位修饰-氨基苯基。通过紫外可见吸收光谱,荧光发射光谱方法研究了BODIPYs的单线态氧的产生和光物理性质。发现这些BODIPY衍生物是环境敏感的和荧光光敏剂,其在中等极性环境中显示出产生单线态氧的高效率,而在极性和非极性溶剂中几乎没有光活性。同时,它们在非极性溶剂中具有高荧光性,但在极性溶剂中的发射性低得多,ICT发射发生在中等极性溶剂中,并且与单线态氧的形成效率相关。该结果通过PCT(光致电荷转移)机理来解释。在1和7位上甲基的存在会导致苯环无法旋转,因此,与BODIPY 1b 2b3b相比, 1a 2a3a的单线态氧产生效率和荧光量子产率明显高。

更新日期:2017-10-16
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