1,3,5,7,8-Pentamethyl-2,6-di(trimethylsilylethynyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene | CAS 1394861-84-7

1,3,5,7,8-Pentamethyl-2,6-di(trimethylsilylethynyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene, a member of the boron-dipyrromethene (BODIPY) family, is a highly functionalized organic compound with distinct structural features. The molecule consists of a BODIPY core, which incorporates a boron atom coordinated to a dipyrromethene ligand, alongside multiple methyl groups and two trimethylsilylethynyl substituents. The trimethylsilylethynyl groups enhance the solubility and electronic properties of the compound, while the difluoro groups further stabilize the structure, optimizing its photophysical performance. This combination of modifications imparts the molecule with robust fluorescence characteristics, making it useful for a wide range of applications.

One of the key applications of 1,3,5,7,8-Pentamethyl-2,6-di(trimethylsilylethynyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene is in fluorescence-based biological imaging. The compound’s strong fluorescence and high quantum yield make it an ideal candidate for cellular and molecular imaging, enabling the tracking of biological processes in living cells. Its excellent photostability allows for long-term imaging studies, making it suitable for real-time monitoring of dynamic events in live-cell environments. This property is particularly valuable for applications such as protein localization, gene expression studies, and monitoring cellular interactions in various biological research fields.

Another significant application is in chemical sensing. The presence of trimethylsilylethynyl groups enhances the compound's sensitivity to various chemical analytes. Due to its strong fluorescence response to changes in environmental conditions, such as pH, ionic strength, or the presence of metal ions, the molecule can be employed as a sensor for detecting a wide range of chemical substances. This capability makes it useful in environmental monitoring, industrial process control, and diagnostic applications, where accurate detection of specific chemical agents is required. The compound’s high sensitivity and selectivity contribute to its value in analytical chemistry and sensor development.

In addition to its role in imaging and sensing, this BODIPY derivative is also applied in photodynamic therapy (PDT). When exposed to light, the compound generates reactive oxygen species (ROS), which can be used to selectively target and destroy cancerous cells or pathogens. The molecule's excellent light absorption properties, coupled with its ability to generate ROS upon light activation, make it a promising photosensitizer for cancer therapy and antimicrobial treatment. The trimethylsilylethynyl groups improve its solubility and stability in biological systems, enhancing its effectiveness in therapeutic applications.

Finally, 1,3,5,7,8-Pentamethyl-2,6-di(trimethylsilylethynyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene is utilized in the field of optoelectronics, particularly in the development of organic light-emitting diodes (OLEDs) and organic solar cells. The molecule's strong fluorescence, combined with its high stability and excellent electronic properties, makes it an ideal material for optoelectronic devices. It is used to enhance the efficiency and performance of OLED displays, as well as organic solar cells. The trimethylsilylethynyl groups contribute to the molecule's solubility and ease of integration into electronic materials, improving the overall functionality and longevity of devices that incorporate this compound.