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Crystals 2017, 7(1), 25; doi:10.3390/cryst7010025

Four Thermochromic o-Hydroxy Schiff Bases of α-Aminodiphenylmethane: Solution and Solid State Study

1
Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia
2
Refining and Marketing Development Sector, Central Testing Laboratory Department, INA Industrija nafte, d.d., Lovinčićeva 4, HR-10000 Zagreb, Croatia
3
Department of Chemistry, University of the Free State, Bloemfontein 9301, South Africa
*
Author to whom correspondence should be addressed.
Academic Editor: Johan Wouters
Received: 15 December 2016 / Revised: 9 January 2017 / Accepted: 11 January 2017 / Published: 14 January 2017
(This article belongs to the Special Issue Thermo- and Photochromic Molecular Crystals)

Abstract

More than a hundred years after the first studies of the photo- and thermochromism of o-hydroxy Schiff bases (imines), it is still an intriguing topic that fascinates several research groups around the world. The reasons for such behavior are still under investigation, and this work is a part of it. We report the solution-based and mechanochemical synthesis of four o-hydroxy imines derived from α-aminodiphenylmethane. The thermochromic properties were studied for the single crystal and polycrystalline samples of the imines. The supramolecular impact on the keto-enol tautomerism in the solid state was studied using SCXRD and NMR, while NMR spectroscopy was used for the solution state. All four imines are thermochromic, although the color changes of the single crystals are not as strong as of the polycrystalline samples. One of the imines shows negative thermochromism, and that one is in keto-amine tautomeric form, both in the solid state as in solution. View Full-Text
Keywords: thermochromism; Schiff base; keto-enol tautomerism; solution-based synthesis; mechanosynthesis thermochromism; Schiff base; keto-enol tautomerism; solution-based synthesis; mechanosynthesis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Zbačnik, M.; Pičuljan, K.; Parlov-Vuković, J.; Novak, P.; Roodt, A. Four Thermochromic o-Hydroxy Schiff Bases of α-Aminodiphenylmethane: Solution and Solid State Study. Crystals 2017, 7, 25.

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