Water-soluble and fluorescent perylene dyes PMI1 and PMI2 with red to near-infrared (red-NIR) emission and a large Stokes shift were designed and synthesized. These dyes were designed to have two binding units (an aromatic perylene-core and a cationic side group) that allow PMI1 and PMI2 to form strong host–guest complexes with cucurbit[8]uril (CB8) through hydrophobic and electrostatic interactions. As a result, the binding constant of the resulting complexes was determined to be in the range of 10⁶ M⁻¹ which increased about 2 orders of magnitude compared to the previously reported perylene dye with only one binding unit. The results also revealed that the fluorescence emission of PMI1 or PMI2 only in aqueous solution is very low due to the aggregation effect. Upon complexation with CB8, the fluorescence intensity increased about 10-fold while the red-NIR emission and the large Stokes shift were preserved. These host–guest complexes can serve as red-NIR fluorescent displacement probes for the detection of CB8 binding guests. The successful detection of addictive drugs in urine was further demonstrated using the host–guest CB8·PMI1 complex and the interference of autofluorescence from the urine sample was successfully eliminated.

中文翻译：

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超分子红至近红外荧光探针，用于检测尿液中的药物

设计并合成了具有红色至近红外（red-NIR）发射和大Stokes位移的水溶性和荧光per染料PMI1和PMI2。这些染料被设计成具有两个结合单元（一个芳香族per核和一个阳离子侧基），允许PMI1和PMI2通过疏水和静电相互作用与葫芦[8] uril（CB8）形成牢固的主体-客体复合物。结果，确定所得复合物的结合常数在10 ⁶ M ^-1的范围内，与先前报道的仅具有一个结合单元的per染料相比，其增加了约2个数量级。结果还表明，由于聚集效应，仅水溶液中的PMI1或PMI2非常低。与CB8络合后，荧光强度增加了约10倍，同时保留了红色近红外发射和较大的斯托克斯位移。这些宿主-客体复合物可作为红色-NIR荧光置换探针，用于检测CB8结合客体。使用宿主-客体CB8 · PMI1复合物进一步证明了尿中成瘾药物的成功检测，尿样品中自发荧光的干扰得以成功消除。