Stability and physical structure tests of piperidyl and morpholinyl derivatives of diphenyl-diketo-pyrrolopyrroles (DPP) |
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Authors: | Ji?í Ku?erík Jan David Martin Weiter Martin Vala Jan Vyňuchal Imad Ouzzane Ota Salyk |
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Institution: | (1) Institute of Environmental Sciences, University of Koblenz-Landau, Fortstrasse 7, 768 29 Landau, Germany;(2) Faculty of Chemistry, Brno University of Technology, Purkyňova 118, Brno, 612 00, Czech Republic;(3) Faculty of Chemistry, Centre for Materials Research CZ.1.05/2.1.00/01.0012, Brno University of Technology, Purkyňova 464/118, Brno, 612 00, Czech Republic;(4) Research Institute of Organic Syntheses, Rybitv? 296, 533 54, Czech Republic |
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Abstract: | Crystalline structure, thermo-oxidative and thermal stability of symmetrical and asymmetrical piperidyl and morpholinyl derivatives
of both N-substituted and non-N-substituted butyl diphenyl-diketo-pyrrolopyrrole (DPP) pigments were studied using differential
scanning calorimetry (DSC) and thermogravimetry (TG). Except for the asymmetrical morpholine DPP derivative, all the samples
showed melting peaks which were relatively close to their degradation temperatures (from 260 to 430 °C). Using DSC, monotropic
polymorphism was revealed in the symmetrical piperidyl-N-butyl-derivative which confirmed earlier observation about tendency of symmetrical N-alkyl DPP derivates to form several crystalline structures. TG carried out under nitrogen atmosphere served for distinguishing
of evaporation/sublimation and degradation temperatures. Temperatures of evaporation/sublimation were typically 10–30 °C lower
in comparison with temperatures of thermal degradation. The highest thermal (450 °C) and thermo-oxidative stability (around
360 °C) showed the DPP derivatives containing morpholine moieties with no alkyl substitution on NH-group of DPP core. The
presence of the latter was found to be the most destabilizing factor. Piperidyl group showed more stabilizing effect due to
its polar character and its influence on π–π intermolecular interactions of neighbouring phenyl groups. The highest stabilizing
effect of morpholine moiety on DPP structure was explained based on the presence of polar oxygen atom in that group. The preparations
of 3,6-di-(4-morpholinophenyl)-2,5-dihydro-pyrrolo3,4-c]pyrrole-1,4-dione and 3-(phenyl)-6-(4-morpholinophenyl)-2,5-dihydropyrrolo3,4-c]pyrrole-1,4-dione are reported. |
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