Adopting the rarely used β-functionalisation strategy in porphyrin-based sensor design, an amine receptive site is appended onto the zinc(II) porphyrin molecular framework affording a ditopic chemosensor 4. The assembled chemosensor interacts selectively with histamine in toluene via a ‘two-site’ binding mode. Association constant of the complex evaluated from the respective UV–vis spectra is found to be (2.32 ± 0.57) × 106, which is approximately 4-fold greater than those complexes derived from 4 and nicotine/histidine. On the basis of a combined spectroscopic method and molecular modelling, the binding model of the porphyrin host and biogenic guest molecules is established. Our results clearly demonstrate the viability of the design and development of the porphyrin-based chemosensor by appending a receptor at the β-pyrrolic carbon of the porphyrin scaffold.

中文翻译：

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在 β-吡咯碳上添加带有胺受体的四苯基卟啉锌以设计选择性组胺化学传感器

在基于卟啉的传感器设计中采用很少使用的 β-官能化策略，将胺接受位点附加到锌 (II) 卟啉分子框架上，提供双位化学传感器 4。组装的化学传感器通过“双-”选择性地与甲苯中的组胺相互作用。站点的绑定模式。发现从各自的 UV-vis 光谱评估的复合物的缔合常数为 (2.32 ± 0.57) × 106，比源自 4 和尼古丁/组氨酸的复合物大约 4 倍。在结合光谱方法和分子建模的基础上，建立了卟啉宿主和生物客体分子的结合模型。