H-Aggregated π-Systems Based on Disulfide-Linked Dimers of Dipyrrolyldiketone Boron Complexes.

J Org Chem

Department of Applied Chemistry, College of Life Sciences, Ritsumeikan University, Kusatsu 525-8577, Japan.

Published: October 2017

Dipyrrolyldiketone boron complexes linked by a disulfide bond were synthesized, forming H-aggregated dimers assisted by intramolecular π-π and hydrogen-bonding interactions. The conformations of the dimers, with small C-S-S-C dihedral angles, were examined by UV-vis absorption and H NMR spectra as well as single-crystal X-ray analysis and theoretical studies.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.joc.7b02185DOI Listing

Publication Analysis

Top Keywords

dipyrrolyldiketone boron
8
boron complexes
8
h-aggregated π-systems
4
π-systems based
4
based disulfide-linked
4
disulfide-linked dimers
4
dimers dipyrrolyldiketone
4
complexes dipyrrolyldiketone
4
complexes linked
4
linked disulfide
4

Similar Publications

Article Synopsis
  • Researchers synthesized guinoidal molecules using diyrrolyldiketone complexes with pyrrole units connected by a partially conjugated system, which acted as a singlet spin coupler.
  • The introduction of a benzo unit stabilized a closed-shell tautomer conformation, allowing the molecules to show near-infrared absorption, particularly in deprotonated forms.
  • The study highlighted cation-dependent diradical properties and demonstrated that the singlet diradical is more stable than the triplet diradical through VT NMR, ESR, and theoretical analyses.
View Article and Find Full Text PDF

A variety of naphthalenediolates were orthogonally introduced to the boron unit of dipyrrolyldiketone boron complexes, exhibiting electronic properties that depended on the substituting positions of the naphthyl moieties. Combining the anion complexes with countercations resulted in the formation of ion-pairing assemblies with supporting stacking interactions of the naphthyl units.

View Article and Find Full Text PDF

In this study, the diverse derivatives of dipyrrolyldiketone boron complexes as anion-responsive π-electronic systems were synthesized via the Huisgen cycloaddition of an ethynyl-substituted anion receptor and azide derivatives. The obtained triazole-substituted anion receptors showed effective anion-binding behaviors and ion-pairing assemblies comprising receptor-anion complexes and countercations. Solid-state ion-pairing structures were modulated according to the introduced azide moieties along with coexisting bulky and π-electronic cations.

View Article and Find Full Text PDF

Two-photon absorption (TPA) dyes with intense fluorescence can be used to detect small chemical species and as sensors and bioimaging probes for specific analytes. Various TPA dyes responding to a number of external stimuli have been reported. Among them, biologically important anionic species have not been used as agents to control TPA properties because their direct electronic influences on the transition dipole moments of dyes are typically small.

View Article and Find Full Text PDF

Multiply aryl-substituted pyrrole-based anion-responsive π-electronic molecules were synthesized. The effects of the introduced aryl moieties on solution-state emissive behaviours were examined, depending on the solvent polarity and anion binding.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!