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1,8-Diamidocarbazoles: an easily tuneable family of fluorescent anion sensors and transporters†
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2018-06-29 00:00:00 , DOI: 10.1039/c8ob01031e Krzysztof M. Bąk 1, 2, 3, 4, 5 , Krzysztof Chabuda 1, 2, 3, 4, 5 , Helena Montes 6, 7, 8, 9 , Roberto Quesada 6, 7, 8, 9 , Michał J. Chmielewski 1, 2, 3, 4, 5
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2018-06-29 00:00:00 , DOI: 10.1039/c8ob01031e Krzysztof M. Bąk 1, 2, 3, 4, 5 , Krzysztof Chabuda 1, 2, 3, 4, 5 , Helena Montes 6, 7, 8, 9 , Roberto Quesada 6, 7, 8, 9 , Michał J. Chmielewski 1, 2, 3, 4, 5
Affiliation
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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.
中文翻译：
1,8-二酰胺基咔唑：易于调节的荧光阴离子传感器和转运蛋白系列†
描述了广泛，合理设计的一系列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。尽管结构简单且仅存在三个氢键供体，但此类化合物还是DMSO + 0.5％H 2 O中氧阴离子的强而有选择性的受体。由于具有咔唑荧光团，它们还是H 2的灵敏开启荧光传感器PO 4 -和ACO -结合后荧光强度增加超过15倍。尽管氯化物亲和力相对较弱，但某些二酰胺基咔唑也首次被证明是通过脂质双层的非常活跃的氯化物转运蛋白。这些受体的结合，感测和转运特性可以通过其烷基侧臂的长度和支化程度通常被忽视的变化而容易地调节。总体而言，这项研究表明，1,8-二氨基咔唑结合单元是开发荧光传感器和阴离子转运蛋白的非常有前途且综合用途广泛的平台。
更新日期：2018-06-29
中文翻译：
1,8-二酰胺基咔唑：易于调节的荧光阴离子传感器和转运蛋白系列†
描述了广泛，合理设计的一系列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。尽管结构简单且仅存在三个氢键供体，但此类化合物还是DMSO + 0.5％H 2 O中氧阴离子的强而有选择性的受体。由于具有咔唑荧光团，它们还是H 2的灵敏开启荧光传感器PO 4 -和ACO -结合后荧光强度增加超过15倍。尽管氯化物亲和力相对较弱，但某些二酰胺基咔唑也首次被证明是通过脂质双层的非常活跃的氯化物转运蛋白。这些受体的结合，感测和转运特性可以通过其烷基侧臂的长度和支化程度通常被忽视的变化而容易地调节。总体而言，这项研究表明，1,8-二氨基咔唑结合单元是开发荧光传感器和阴离子转运蛋白的非常有前途且综合用途广泛的平台。
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