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Stability and physical structure tests of piperidyl and morpholinyl derivatives of diphenyl-diketo-pyrrolopyrroles (DPP)

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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-pyrrolo[3,4-c]pyrrole-1,4-dione and 3-(phenyl)-6-(4-morpholinophenyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione are reported.

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Acknowledgements

The financial support of the Ministry of Education of the Czech Republic - project MSM 0021630501, Academy of Sciences of the Czech Republic project KAN401770651 and Czech Science Foundation project GACR 203/08/1594 are acknowledged. This study was also supported by the project “Centre for Materials Research at FCH BUT” No. CZ.1.05/2.1.00/01.0012 from ERDF.

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Authors and Affiliations

  1. Institute of Environmental Sciences, University of Koblenz-Landau, Fortstrasse 7, 768 29, Landau, Germany

    Jiří Kučerík

  2. Faculty of Chemistry, Brno University of Technology, Purkyňova 118, Brno, 612 00, Czech Republic

    Jiří Kučerík, Jan David, Martin Weiter, Martin Vala & Ota Salyk

  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

    Jan David, Martin Weiter, Martin Vala & Imad Ouzzane

  4. Research Institute of Organic Syntheses, Rybitví 296, 533 54, Czech Republic

    Jan Vyňuchal

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  1. Jiří Kučerík
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Correspondence to Jiří Kučerík.

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Kučerík, J., David, J., Weiter, M. et al. Stability and physical structure tests of piperidyl and morpholinyl derivatives of diphenyl-diketo-pyrrolopyrroles (DPP). J Therm Anal Calorim 108, 467–473 (2012). https://doi.org/10.1007/s10973-011-1896-8

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  • DOI: https://doi.org/10.1007/s10973-011-1896-8

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