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Volume: 55 | Article ID: art00008
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Electronic Structure of 4,6-bis{5-amino-3-tert-butyl-4-[(3-methyl-1,2,4-thiadiazol-5-yl)diazeneyl]-1H-pyrazol-1-yl}-1,3,5-triazin-2(1H)-one of the trans Form Used for Yellow Ink Jet Inks
  DOI :  10.2352/J.ImagingSci.Technol.2011.55.2.020505  Published OnlineMarch 2011
Abstract

The authors have been interested in a sodium-containing bisazo complex of the cis form for application as a yellow ink jet ink pigment. It exhibits good performance with respect to light and heat stability but is rather poor with respect to solvent fastness. Accordingly, an attempt has been made in the present investigation to improve the solvent fastness by eliminating the sodium atom from the Na complex to give a structurally more stable bisazo compound of the trans form (i.e., the title compound). Treatment of the complex with hydrochloric acid removed the sodium atom and also transformed the product from the cis to the trans form, shown by the structural analysis as reported in the companion article. In this article, the authors report electronic characterization which was carried out computationally and experimentally. The absorption maximum in solution appears at about 450 nm and is composed of two electronic transitions with the following configuration interaction (CI) components: (i) HOMO-1→LUMO and HOMO→LUMO+1 and (ii) HOMO→LUMO+1, HOMO→LUMO+2 and HOMO-1→LUMO, where the HOMO, LUMO, and CI stand for the highest occupied or the lowest unoccupied molecular orbitals and the configuration interaction, respectively. The title compound possesses high solvent fastness in addition to the light and heat stability of the original compound.

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Hiroki Shibata, Jin Mizuguchi, "Electronic Structure of 4,6-bis{5-amino-3-tert-butyl-4-[(3-methyl-1,2,4-thiadiazol-5-yl)diazeneyl]-1H-pyrazol-1-yl}-1,3,5-triazin-2(1H)-one of the trans Form Used for Yellow Ink Jet Inksin Journal of Imaging Science and Technology,  2011,  pp 20505-1 - 20505-6,  https://doi.org/10.2352/J.ImagingSci.Technol.2011.55.2.020505

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