1,3,5,7,8-Pentamethyl-2,6-di(phenylethynyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene | CAS 1870842-52-6

1,3,5,7,8-Pentamethyl-2,6-di(phenylethynyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene, commonly known as a boron-dipyrromethene (BODIPY) derivative, is a highly functionalized fluorescent compound. It features a BODIPY core structure, which is characterized by a boron atom coordinated to a dipyrromethene ligand, combined with multiple methyl and phenylethynyl groups. These modifications enhance its optical properties, particularly its fluorescence, making it an ideal candidate for a wide range of applications in material science, biological imaging, and chemical sensing. The presence of difluoro groups further stabilizes the compound, improving its photophysical characteristics.

One of the primary applications of 1,3,5,7,8-Pentamethyl-2,6-di(phenylethynyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene is in fluorescence imaging and biological tracking. Due to its strong fluorescence and high quantum yield, this compound is highly suitable for use in live-cell imaging, biomolecular labeling, and real-time monitoring of cellular processes. The phenylethynyl groups further contribute to the stability and sensitivity of the compound, making it an excellent choice for studying protein interactions, cellular dynamics, and other molecular behaviors in both research and clinical settings.

In addition to biological imaging, this BODIPY derivative plays a critical role in chemical sensing, where its strong fluorescence properties allow for precise detection of a variety of analytes. Its ability to undergo fluorescence changes in response to environmental stimuli, such as metal ions, pH levels, or other chemical species, makes it valuable in both analytical chemistry and environmental monitoring. The compound’s sensitivity to various chemical interactions allows for the development of high-performance sensors that can detect trace levels of specific molecules in complex mixtures.

1,3,5,7,8-Pentamethyl-2,6-di(phenylethynyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene also finds significant application in photodynamic therapy (PDT). In PDT, the compound is used as a photosensitizer that, upon activation by light, generates reactive oxygen species (ROS) capable of selectively damaging target cells, particularly cancerous or bacterial cells. The compound's ability to absorb light efficiently and produce ROS upon illumination makes it a promising candidate for therapeutic applications in cancer treatment, as well as for combating microbial infections. The difluoro and methyl groups improve its solubility and stability, enhancing its efficacy as a therapeutic agent.

Finally, this BODIPY derivative is utilized in the field of optoelectronics, particularly in the development of organic light-emitting diodes (OLEDs) and organic solar cells. Its excellent fluorescence properties, combined with its high stability and ease of functionalization, make it a valuable material for use in light-emitting devices. The compound’s ability to emit light efficiently, along with its stability under operational conditions, contributes to the performance and longevity of OLED displays and solar cell devices. Its tunable optical properties also allow for customization in different optoelectronic applications, enhancing device efficiency and performance.