(E)-10-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)-3-(4-(dimethylamino)styryl)-5,5-difluoro-1,7,9-trimethyl-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide | CAS 949108-72-9

(E)-10-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)-3-(4-(dimethylamino)styryl)-5,5-difluoro-1,7,9-trimethyl-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide is a highly functionalized, boron-containing dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborine compound. It incorporates several key structural motifs, including a boron-dioxaborine group, a dimethylamino-styryl group, and difluoro- and trimethyl modifications. The boron center is critical for the compound’s optical properties, enhancing its fluorescence and making it useful in a range of chemical and biological applications. This highly conjugated system also supports strong light absorption, which is valuable for many advanced technologies.

One of the primary applications of this compound is in fluorescence imaging and sensing. Due to its unique structure, it exhibits excellent fluorescence properties, such as high quantum yield and photostability, making it an ideal candidate for biological imaging applications. It can be used to monitor live cells, track molecular processes, and detect biomolecular interactions in real-time. The dimethylamino-styryl group enhances the molecule’s fluorescence efficiency, making it suitable for high-resolution imaging of cells and tissues in a variety of biological research contexts.

Another important application of this molecule is in chemical sensing, particularly in detecting metal ions and small molecules. The boron-dioxaborine group in the compound allows for selective interactions with metal ions, making it a highly sensitive probe for ion detection. Its strong fluorescence response to environmental changes, such as pH or ionic strength, adds to its versatility in sensing applications. This property is valuable in environmental monitoring, diagnostics, and drug development, where it can be used to detect specific analytes in complex samples.

The compound also plays a crucial role in photodynamic therapy (PDT), where it acts as a photosensitizer. Upon light activation, the molecule generates reactive oxygen species (ROS), which can be used to target and destroy cancerous cells or bacteria. Its ability to generate ROS upon exposure to light makes it a promising candidate for targeted therapies, particularly for cancer treatment and antimicrobial applications. The incorporation of difluorine and trimethyl groups enhances its photochemical properties, allowing for precise control over light absorption and ROS production.

In the field of optoelectronics, (E)-10-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)-3-(4-(dimethylamino)styryl)-5,5-difluoro-1,7,9-trimethyl-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide is utilized in the development of advanced organic light-emitting diodes (OLEDs) and solar cells. The compound's strong absorption and emission properties contribute to efficient light emission, which is crucial for high-performance displays and energy harvesting technologies. Its molecular stability, combined with its tunable fluorescence, allows it to be optimized for use in these devices, enhancing the efficiency and performance of optoelectronic systems.