Unknown

Dataset Information

0

Influencing the Self-Sorting Behavior of [2.2]Paracyclophane-Based Ligands by Introducing Isostructural Binding Motifs.


ABSTRACT: Two isostructural ligands with either nitrile (Lnit ) or isonitrile (Liso ) moieties directly connected to a [2.2]paracyclophane backbone with pseudo-meta substitution pattern have been synthesized. The ligand itself (Lnit ) or its precursors (Liso ) were resolved by HPLC on a chiral stationary phase and the absolute configuration of the isolated enantiomers was assigned by XRD analysis and/or by comparison of quantum-chemical simulated and experimental electronic circular dichroism (ECD) spectra. Surprisingly, the resulting metallosupramolecular aggregates formed in solution upon coordination of [(dppp)Pd(OTf)2 ] differ in their composition: whereas Lnit forms dinuclear complexes, Liso exclusively forms trinuclear ones. Furthermore, they also differ in their chiral self-sorting behavior as (rac)-Liso undergoes exclusive social self-sorting leading to a heterochiral assembly, whereas (rac)-Liso shows a twofold preference for the formation of homochiral complexes in a narcissistic self-sorting manner as proven by ESI mass spectrometry and NMR spectroscopy. Interestingly, upon crystallization, these discrete aggregates undergo structural transformation to coordination polymers, as evidenced by single-crystal X-ray diffraction.

SUBMITTER: Volbach L 

PROVIDER: S-EPMC7154700 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

altmetric image

Publications

Influencing the Self-Sorting Behavior of [2.2]Paracyclophane-Based Ligands by Introducing Isostructural Binding Motifs.

Volbach Lucia L   Struch Niklas N   Bohle Fabian F   Topić Filip F   Schnakenburg Gregor G   Schneider Andreas A   Rissanen Kari K   Grimme Stefan S   Lützen Arne A  

Chemistry (Weinheim an der Bergstrasse, Germany) 20200219 15


Two isostructural ligands with either nitrile (L<sup>nit</sup> ) or isonitrile (L<sup>iso</sup> ) moieties directly connected to a [2.2]paracyclophane backbone with pseudo-meta substitution pattern have been synthesized. The ligand itself (L<sup>nit</sup> ) or its precursors (L<sup>iso</sup> ) were resolved by HPLC on a chiral stationary phase and the absolute configuration of the isolated enantiomers was assigned by XRD analysis and/or by comparison of quantum-chemical simulated and experimenta  ...[more]

Similar Datasets

| S-EPMC8371969 | biostudies-literature
| S-EPMC4660956 | biostudies-literature
| S-EPMC6891757 | biostudies-literature
| S-EPMC8042488 | biostudies-literature
| S-EPMC5238561 | biostudies-literature
| S-EPMC6403781 | biostudies-literature
| S-EPMC6563691 | biostudies-literature
| S-EPMC7698277 | biostudies-literature
| S-EPMC9300155 | biostudies-literature
| S-EPMC8596836 | biostudies-literature