This minireview is devoted to honoring the memory of Dr. Thomas Dougherty, a pioneer of modern photodynamic therapy (PDT). It compiles the most important inputs made by our research group since 2012 in the development of new photosensitizers based on BODIPY chromophore which, thanks to the rich BODIPY chemistry, allows a finely tuned design of the photophysical properties of this family of dyes to serve as efficient photosensitizers for the generation of singlet oxygen. These two factors, photophysical tuning and workable chemistry, have turned BODIPY chromophore as one of the most promising dyes for the development of improved photosensitizers for PDT. In this line, this minireview is mainly related to the establishment of chemical methods and structural designs for enabling efficient singlet oxygen generation in BODIPYs. The approaches include the incorporation of heavy atoms, such as halogens (iodine or bromine) in different number and positions on the BODIPY scaffold, and also transition metal atoms, by their complexation with Ir(III) center, for instance. On the other hand, low‐toxicity approaches, without involving heavy metals, have been developed by preparing several orthogonal BODIPY dimers with different substitution patterns. The advantages and drawbacks of all these diverse molecular designs based on BODIPY structural framework are described.
In this work, hemicyanine dye LDS 722 is encapsulated into the 1D elliptical nanochannels of MgAPO‐11 aluminophosphate by a crystallization inclusion method. The synthesis of the hybrid material has been optimized through a systematic variation of the crystallization conditions in order to obtain pure and large crystals (around 20 μm×30 μm) suitable for optical applications. The tight fitting between the molecular size of the guest dye and the pore dimensions of the host has favored a rigid planar conformation of the dye, restricting its inherent flexibility, which is confirmed by molecular simulations. Consequently, the encapsulation of LDS 722 into MgAPO‐11 has led to an astonishing enhancement of the fluorescence with respect to the dye into MgAPO‐5, with slightly larger cylindrical channels, and with respect to the dye in solution. Moreover, the perfect alignment of LDS 722 (dye with intrinsic nonlinear‐optical properties) along the channels of MgAPO‐11 has revealed attractive second‐order nonlinear properties, such as second harmonic generation, proven through microscopy measurements in single crystals.
The detailed triplet and singlet state characterization of 3,5-dimethyl-2,6-diiodo-8-thiomethyl-pyrromethene (MeSBDP), a promising standard sensitizer for singlet oxygen production.
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