π-π-Induced aggregation and single-crystal fluorescence anisotropy of 5,6,10b-tri-aza-acephenanthrylene

IUCrJ
Katarzyna OstrowskaAndrzej M Turek

Abstract

The structural origin of absorption and fluorescence anisotropy of the single crystal of the π-conjugated heterocyclic system 5,6,10b-tri-aza-acephenan-thrylene, TAAP, is presented in this study. X-ray analysis shows that the crystal framework in the space group P [Formula: see text] is formed by centrosymmetric dimers of face-to-face mutually oriented TAAP molecules joined by π-π non-covalent interactions. The conformation of the TAAP molecule is stabilized by intramolecular C-H⋯N(sp2), N(sp2)H⋯π(CN), and C-H⋯O(sp2) hydrogen bonds. The presence of weak π-π interactions is confirmed by quantum theory of atoms in molecules (QTAIM) and non-covalent interaction (NCI) analysis. The analysis of the optical spectra of TAAP in solution and in the solid state does not allow the specification of the aggregation type. DFT calculations for the dimer in the gas phase indicate that the lowest singlet excitation is forbidden by symmetry, suggesting H-type aggregation, even though the overall absorption spectrum is bathochromically shifted as for the J-type. The experimental determination of the permanent dipole moment of a TAAP molecule in 1,4-dioxane solution indicates the presence of the monomer form. The calculated absorption and emission...Continue Reading

References

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Citations

Jun 28, 2019·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Apurba K DasTushar K Mukherjee
Sep 14, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Francisco J MelendezRené Gutiérrez-Pérez
May 16, 2020·Inorganic Chemistry·R Lee AyscueKarah E Knope

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Methods Mentioned

BETA
confocal microscopy
X-ray
light microscopy
NMR

Software Mentioned

Nicols
CrysAlisPro
NCIPLOT
GAUSSIAN09
SHELXL
QTAIM
AIMAll

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