Abstract
The structural parameters for the cyclobutanoQ[5–8] family were determined through single crystal X-ray diffraction. It was found that the electropositive cyclobutano methylene protons (CH2) are important in forming interlinking crystal packing arrangements driven by the dipole–dipole interactions between these protons and the portal carbonyl O of a near neighbor. This type of interaction was observed across the whole family. Electrostatic potential maps also confirmed the electropositive nature of the cyclobutano CH2 but, more importantly, it was established that the cavities are electronegative in contrast to classical Q[5–8], which are near neutral.
Highlights
IntroductionJust prior to our reporting of the synthesis of the fully substituted CyB8 Q[8] the partially substituted Me4 Q[8] and CyH2 Q[8] were the only higher homologues (n = 8) carrying substitution that are prepared by condensation and cyclo-oligomerization (Figure 1, bottom Rx Q[n]) [31]
Introduction a Crystal Packing DriverMoleculesCucurbit[n]uril have been shown to exhibit a wide range of potential applications in various fields, through leveraging the properties of this macrocyclic family and by the selection of a cavity with an appropriate size
Recent examples demonstrate this with targeted cell imaging [1], human cancer assay [2], Q[n]-based supramolecular frameworks (QSFs) [3,4], sensors [5,6,7,8], fluorescent imprintable hydrogels [9], fluorescent probes [10,11,12], nitroxide radical probes [13], the preparation of adsorbent or solid fluorescent materials [14], room-temperature phosphorescence (RTP) [15,16], light-harvesting systems [17], nanocapsules [18], nanofiltration membranes [19] molecular machines [20,21,22] reductive catalysis of CO2 [23], and gold recovery [24]
Summary
Just prior to our reporting of the synthesis of the fully substituted CyB8 Q[8] the partially substituted Me4 Q[8] and CyH2 Q[8] were the only higher homologues (n = 8) carrying substitution that are prepared by condensation and cyclo-oligomerization (Figure 1, bottom Rx Q[n]) [31]
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