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.
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http://dx.doi.org/10.1021/acs.joc.7b02185 | DOI Listing |
J Am Chem Soc
April 2023
Department of Applied Chemistry, College of Life Sciences, Ritsumeikan University, Kusatsu 525-8577, Japan.
Org Lett
February 2023
Department of Applied Chemistry, College of Life Sciences, Ritsumeikan University, Kusatsu 525-8577, Japan.
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 PDFJ Org Chem
June 2022
Diffraction and Scattering Division, Japan Synchrotron Radiation Research Institute, Sayo 679-5198, Japan.
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 PDFChemistry
March 2020
Department of Applied Chemistry, College of Life Sciences, Ritsumeikan University, Kusatsu 5, 25-8577, Japan.
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 PDFChem Commun (Camb)
July 2019
Department of Applied Chemistry, College of Life Sciences, Ritsumeikan University, Kusatsu 525-8577, Japan.
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.
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