Faculty of Chemistry, Biological and Chemical Research Centre, University of Warsaw, Żwirki i Wigury 101, 02-089 Warszawa, Poland.
Org Biomol Chem. 2018 Jul 18;16(28):5188-5196. doi: 10.1039/c8ob01031e.
The synthesis, structure and anion recognition properties of an extensive, rationally designed series of bisamide derivatives of 1,8-diaminocarbazole and 1,8-diamino-3,6-dichlorocarbazole are described. Despite simple structures and the presence of only three hydrogen bond donors, such compounds are remarkably strong and selective receptors for oxyanions in DMSO + 0.5%H2O. Owing to their carbazole fluorophore, they are also sensitive turn-on fluorescent sensors for H2PO4- and AcO-, with a more than 15-fold increase in fluorescence intensity upon binding. Despite relatively weak chloride affinity, some of the diamidocarbazoles have also been shown, for the first time, to be very active chloride transporters through lipid bilayers. The binding, sensing and transport properties of these receptors can be easily modulated by the usually overlooked variations in the length and degree of branching of their alkyl side arms. Overall, this study demonstrates that the 1,8-diamidocarbazole binding unit is a very promising and synthetically versatile platform for the development of fluorescent sensors and transporters for anions.
描述了一系列广泛的、经过合理设计的 1,8-二氨基咔唑和 1,8-二氨基-3,6-二氯咔唑的双酰胺衍生物的合成、结构和阴离子识别特性。尽管这些化合物结构简单，只有三个氢键供体，但它们是在 DMSO + 0.5%H2O 中对氧阴离子具有显著的强选择性受体。由于它们的咔唑荧光团，它们也是对 H2PO4-和 AcO-的灵敏的荧光传感器，结合后荧光强度增加超过 15 倍。尽管对氯的亲和力相对较弱，但一些二酰胺咔唑化合物首次被证明是通过脂质双层非常活跃的氯离子转运体。这些受体的结合、传感和传输特性可以很容易地通过其烷基侧链的长度和分支程度的通常被忽视的变化来调节。总的来说，这项研究表明，1,8-二酰胺咔唑结合单元是开发阴离子荧光传感器和转运体的非常有前途和具有合成多功能性的平台。
