We disclose an interesting concept for developing heavy atom-free chemiluminogenic photosensitizers. To accomplish this, conjugates 2 and 3, which are composed of boron-dipyrromethene (BODIPY) and 2,3-dihydrophthalazine-1,4dione units, are investigated. 2 and 3 are compared in terms of their photophysical properties, chemiluminescence responses, and singlet oxygen production. Strikingly, the results indicate that decoration of BODIPY with the 2,3-dihydrophthalazine-1,4dione scaffold boosts the singlet oxygen generation. Furthermore, treatment of epidermoid laryngeal carcinoma Hep-2 (Hep-2) cells with conjugates 2 and 3 results in efficient cellular internalization which ensures live-cell imaging of Hep-2 cells. Finally, it is noteworthy that in vitro cytotoxicity assays reveal that both 2 and 3 induce cytotoxicity when illuminated with red light. Thus, 2 and 3 represent heavy atom-free chemiluminogenic photosensitizers.
The title compound, C17H14Cl4N5OP3, is a spiro-phosphazene derivative with bulky naphthalene and pyridine rings. The phosphazene and the six-membered N/O rings are in flattened-boat and twisted-boat conformations, respectively. The naphthalene ring system and the pyridine ring are oriented at a dihedral angle of 18.06 (8)°. In the crystal, weak π–π stacking between the pyridine rings and between the pyridine rings and the naphthalene ring system [centroid–centroid distances = 3.594 (2) and 3.961 (2) Å, respectively] occur. Weak C—H⋯π interactions are also observed. These interactions link the molecules into a three-dimensional supramolecular network.
Aza-boron-dipyrromethenes (Aza-BODIPYs) represent an important class of chromophores absorbing and emitting in the near-infrared (NIR) region. They have unique optical and electronic features and higher physiological and photo stability than other NIR dyes. Especially after the development of facile synthetic routes, Aza-BODIPYs have become indispensable fluors that can find various applications ranging from chemosensors, bioimaging, phototherapy, solar energy materials, photocatalysis, photon upconversion, lasers, and optoelectronics. Herein, we review Aza-BODIPY based fluorescent and colorimetric chemosensors. We show the potential and untapped toolbox of Aza-BODIPY based fluorescent and colorimetric chemosensors. Hence, we divide the fluorescent and colorimetric chemosensors and probes into five sections according to the target analytes. The first section begins with the chemosensors developed for pH. Next, we discuss Aza-BODIPY based ion sensors including, metal ions and anions. Finally, we present the chemosensors and probes concerning reactive oxygen (ROS) and nitrogen species (RNS) along with biologically relevant species in the last two sections. We believe that Aza-BODIPYs are still in their infancy, and they have a promising future for translation from the bench to real biomedical and materials science applications. After two decades of intensive research, it seems that there are many more to come in this already fertile field. Overall, we hope that future work will further expand the applications of Aza-BODIPY in many areas.
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