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BOIMPY: Fluorescent Boron Complexes with Tunable and Environment-Responsive Light-Emitting Properties

机译:BOIMPY:具有可调和响应环境的发光特性的荧光硼配合物

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A series of air-stable boron complexes 1-5 were prepared by using N-aryl iminopyrrolide ligands. Designed as minimalist structural mimics of the privileged BODIPY motif, these new BOIMPY (BOron complexes of IMinoPYrrolide ligands) fluorophores feature low molecular symmetry that promotes emission from CT-type excited states with large Stokes shifts and little self-quenching. Through comparative studies on the homologous set of compounds 1-4, we have confirmed that a delicate interplay between conformational twisting and donor-acceptor interaction dictates the mechanism of de-excitation, which responds sensitively to solvent polarity as well as protonation states. Over a wide visible spectral range, the structure-dependent light-emitting properties of BOIMPY molecules are well manifested, even in the solid-state. In order to exploit the environment-sensitive nature of CT-type emission, the BOIMPY motif was elaborated further into a bioprobe molecule 5. Live-cell fluorescence imaging studies have established that 5 is localized exclusively at lipid droplets to produce well-resolved staining patterns without affecting cell viability. These findings promise future elaboration of BOIMPY-based functional molecules for applications in biological imaging, chemical sensing, and molecular switching.
机译:通过使用N-芳基亚氨基吡咯化物配体制备了一系列空气稳定的硼配合物1-5。这些新的BOIMPY(IMinoPYrrolide配体的硼配合物)设计为特权BODIPY图案的简约结构模拟物,具有低分子对称性,可促进CT型激发态的发射,并具有大的斯托克斯位移和很少的自动猝灭。通过对化合物1-4的同源集合的比较研究,我们已经确认,构象扭曲与供体-受体相互作用之间的微妙相互作用决定了去激励的机理,该机理对溶剂极性以及质子化状态敏感。在宽的可见光谱范围内,即使在固态下,BOIMPY分子的依赖于结构的发光特性也得到了很好的体现。为了利用CT型发射对环境敏感的性质,将BOIMPY基序进一步加工成生物探针分子5。活细胞荧光成像研究已确定5仅位于脂质液滴上,以产生良好分辨的染色模式而不影响细胞活力。这些发现有望为基于BOIMPY的功能分子在生物成像,化学传感和分子转换中的应用做出进一步的开发。

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