期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 20, 期 26, 页码 5308-5318出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2ob00851c
关键词
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资金
- National Science Centre, Poland (SONATA) [2017/26/D/ST5/00361]
- European Union from the European Regional Development Fund under the Operational Programme Innovative Economy, 2007-2013
- European Union under the European Regional Development Fund
This paper describes a method for preparing SDB24C8 and investigates its properties and interactions with metal ions. The results show that the introduction of a sulfonic group can enhance the receptor's affinity and an unusual selectivity of SDB24C8 towards a sodium cation was observed.
In this paper, we describe a method for preparing a monosulfonated dibenzo-24-crown-8 ether, SDB24C8, by direct sulfonation of the parent crown (DB24C8). Since neutral DB24C8 readily interacts with cationic guests, permanently charged SDB24C8 is an advantageous candidate for future supramolecular applications. SDB24C8 can be isolated as a sulfonic acid to be used as it is or converted to a salt of choice. The crystallographic analysis provides the first known host-guest assembly with a DB24C8-based scaffold complexing hydronium and potassium cations. Supramolecular investigations of the interactions of this anionic macrocycle with alkali cations were also performed. According to the expectations, the introduction of the sulfonic group into the DB24C8 scaffold increases the affinities of the receptor. An unusual selectivity of SDB24C8 towards a sodium cation was also observed and further investigated with DFT calculations.
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