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Molecular dynamic staircases: all-carbon axial chiral "Gelander" structures.

ABSTRACT: Herein, the syntheses of two tightly packed all-carbon "Geländer" molecules with axial chirality are described. Motivated by our previous results, we further reduced the bridge length by excluding the heteroatoms. The absolute configuration was determined by comparison of the measured and calculated circular dichroism (CD) spectra and the thermodynamic stability was determined by dynamic high-performance liquid chromatography (HPLC) and CD analysis. The cyclophanes were fully characterized by CD measurements, X-ray diffraction (XRD) analysis, NMR, UV-Vis and high resolution mass spectrometry (HRMS). Our novel all-carbon macrocycle is the most stable Geländer system reported so far.

SUBMITTER: Mannancherry R

PROVIDER: S-EPMC6050599 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature

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Molecular dynamic staircases: all-carbon axial chiral "Geländer" structures.

Mannancherry Rajesh R Rickhaus Michel M Häussinger Daniel D Prescimone Alessandro A Mayor Marcel M

Chemical science 20180605 26

Herein, the syntheses of two tightly packed all-carbon "Geländer" molecules with axial chirality are described. Motivated by our previous results, we further reduced the bridge length by excluding the heteroatoms. The absolute configuration was determined by comparison of the measured and calculated circular dichroism (CD) spectra and the thermodynamic stability was determined by dynamic high-performance liquid chromatography (HPLC) and CD analysis. The cyclophanes were fully characterized by CD ...[more]

PMID: 30079185

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