Korczak Maria L, Maslowska-Jarzyna Krystyna, Chmielewski Michał J
Faculty of Chemistry, Biological and Chemical Research Centre, University of Warsaw Żwirki i Wigury 101 Warsaw 02-089 Poland
RSC Adv. 2024 Sep 19;14(41):29883-29889. doi: 10.1039/d4ra05420b. eCollection 2024 Sep 18.
We describe the synthesis of a new generation of 1,8-diaminocarbazole building blocks for the construction of anion receptors and fluorescent sensors. These new building blocks feature mildly electron-withdrawing ester substituents at positions 3 and 6 of the carbazole core, which improve anion affinities and significantly enhance solubilities, without compromising fluorescent response. To demonstrate the advantages of the new building blocks, three of them were converted into model diamide receptors R1-R3. The resulting ester-substituted receptors showed greatly improved solubilities and fluorescent response in comparison to their 3,6-dichloro-substituted predecessors, while retaining very high affinity and selectivity for oxyanions, particularly dihydrogen phosphate, even in partially aqueous solutions. In view of these promising results and the known synthetic versatility of primary amines, we envisage that the new building blocks will be useful for the construction of various classes of fluorescent anion receptors with improved solubility, affinity, and fluorescent response.
我们描述了用于构建阴离子受体和荧光传感器的新一代1,8 - 二氨基咔唑构建模块的合成。这些新的构建模块在咔唑核心的3位和6位具有吸电子能力较弱的酯取代基，这提高了阴离子亲和力并显著增强了溶解性，同时不影响荧光响应。为了证明新构建模块的优势，将其中三个转化为模型二酰胺受体R1 - R3。与它们的3,6 - 二氯取代的前身相比，所得的酯取代受体显示出大大提高的溶解性和荧光响应，同时即使在部分水溶液中对氧阴离子，特别是磷酸二氢根，仍保持非常高的亲和力和选择性。鉴于这些有前景的结果以及伯胺已知具有的合成多功能性，我们设想新的构建模块将有助于构建各类具有改善的溶解性、亲和力和荧光响应的荧光阴离子受体。
