Solid state fluorescence of Pigment Yellow 101 and derivatives: a conserved property of the individual molecules

Physical Chemistry Chemical Physics : PCCP
Jürgen Plötner, Andreas Dreuw

Abstract

The optical properties of the bisazomethine pigments Pigment Yellow 101 (P.Y.101) and three derivatives are investigated employing density functional theory (DFT) and time-dependent DFT (TDDFT). P.Y.101 and one of its derivatives exhibit unusual solid state fluorescence, although both possess OH groups and the latter pigment has particularly small intermolecular distances in its crystal, which are both properties that contradict common empirical rules for fluorescent pigments. Here it is shown that the OH groups are indeed essential for molecular fluorescence of the pigments due to the necessary formation of an intramolecular hydrogen bond with the lone pairs of the bisazomethine nitrogens. Furthermore, the quenching mechanism of molecular fluorescence in the non-fluorescent derivatives is analyzed in detail and a CNN bending motion of the central bisazomethine substructure is identified to be the relevant reaction coordinate along which efficient fluorescence quenching occurs in the individual molecule as well as in the crystal. Electron transfer quenching, which usually is expected to be an important quenching mechanism in aggregated media (here the crystals), is ruled out for the studied bisazomethine pigments. The solid sta...Continue Reading

References

Sep 15, 1988·Physical Review A: General Physics·A D Becke
Jun 15, 1986·Physical Review. B, Condensed Matter·J P Perdew
Dec 3, 2002·Analytical Sciences : the International Journal of the Japan Society for Analytical Chemistry·Guo-Qing Shi, Guibin Jiang
Nov 10, 2005·Chemical Reviews·Andreas Dreuw, Martin Head-Gordon

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Citations

Feb 13, 2013·Chemistry Central Journal·Anife AhmedovaLiudmil Antonov
Apr 5, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·María Judith PercinoEnrique Pérez-Gutiérrez
Jan 16, 2015·Physical Chemistry Chemical Physics : PCCP·Jonathan J DuDavid E Hibbs
May 20, 2008·Food Additives & Contaminants. Part A, Chemistry, Analysis, Control, Exposure & Risk Assessment·Xiaoyan LiuMancang Liu
Jun 6, 2021·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Bruno B N S BrandãoHenrique E Toma

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