Subphthalocyanine-spiropyran - a versatile system to study photoswitchable fluorescence

荧光是共轭π系统的一种——有时是不必要的——特性，它构成了有机电子中使用的所有材料的基础。精确控制材料的发光可用于光存储器件。这可以通过将感光色素带入荧光团附近来实现。切换光致变色部分可以熄灭荧光团的发射。本项目利用螺吡喃作为光色素影响亚酞菁硼（SubPcs）的发射特性。子粒子被应用于有机光伏或发光二极管中。与螺吡喃化合物的结合为研究光开关对SubPc发射的影响提供了可能。在SubPc中，两种不同的连接几何形状连接到螺吡喃的三个不同位置是可行的。除了通过近距离传递能量外，螺吡喃还可以直接影响SubPcs中的芳烃体系。根据连接位点的不同，螺吡喃可以作为电子供体或受体，也可以与SubPc的pi系统解耦。在一个电环打开成merocyanine形式后，这些电子影响被逆转。有了这些通用的构建模块，就有可能设计和研究作为ON/OFF或OFF/ON光可切换荧光团的系统。

Fluorescence is a – sometimes unwanted – property of conjugated pi systems that form the basis for all materials that are used in organic electronics. Precise control of a material’s luminescence can be utilized in optical memory devices. This can be achieved by bringing a photochrome into the proximity of the fluorophore. Switching the photochromic moiety can quench the emission of the fluorophore.This project utilizes spiropyran as photochrome to influence the emission properties of boron subphthalocyanines (SubPcs). SubPcs were applied in organic photovoltaics or light emitting diods. The combination with spiropyrans provides the possibility to study the influence of the photoswitch on the SubPc’s emission. At the SubPc, two different linking geometries to three distinct sites of the spiropyran are feasible. Beside energy transfer through close distances, spiropyran can directly influence the aromatic system in SubPcs. Depending on the linking site, spiropyran acts either as electron donor or acceptor, or is decoupled from the pi system of SubPc. After an electrocyclic ring opening to the merocyanine form, these electronic influences are reversed. With these versatile building blocks, it will be possible to design and study systems that act as ON/OFF or OFF/ON photoswitchable fluorophore.