Publication detail

Stability and structural aspects of diketopyrrolopyrrole pigment and its N-alkyl derivatives

DAVID, J. WEITER, M. VALA, M. VYŇUCHAL, J. KUČERÍK, J.

Original Title

Type

journal article - other

Language

English

Original Abstract

An unsubstituted sample, three symmetrically N-substituted samples (methyl, butyl and heptyl) and two asymmetrically N-substituted samples (butyl and heptyl) of 3,6-diphenyl-2,5-dihydro-pyrrolo[3,4-c] pyrrole-1,4-dione (DPP) were investigated using thermogravimetry and differential scanning calorimetry to reveal the influence on physical-chemical properties of different alkyl chains and symmetry of Nsubstitution. Stability tests revealed that in all cases the substitution brought significant destabilization of the structure in comparison with the unsubstituted DPP molecule. It was demonstrated that the length of the substituting alkyl chain is a crucial factor in the stability of N-alkyl derivatives; the shorter the alkyl chain was, the less stable was the derivative. Further, the symmetrical derivates were less stable than the asymmetrical ones. Unlike the unsubstituted DPP molecule, all the derivatives showed remarkable sensitivity to different cooling regimes which lead to the revealing of monotropical polymorphism in the symmetrical butyl and heptyl derivatives crystalline structure.

Keywords

Diphenyl-diketo-pyrrolo-pyrroles (DPPs); Pigments; Organic electronics; Thermal stability; Thermogravimetry; Calorimetry

Authors

DAVID, J.; WEITER, M.; VALA, M.; VYŇUCHAL, J.; KUČERÍK, J.

RIV year

2011

Released

2. 4. 2011

Publisher

Elsevier

Location

ISBN

0143-7208

Periodical

DYES AND PIGMENTS

Year of study

Number

State

United Kingdom of Great Britain and Northern Ireland

Pages from

137

Pages to

143

Pages count

BibTex

@article{BUT51019,
  author="Jan {David} and Martin {Weiter} and Martin {Vala} and Jan {Vyňuchal} and Jiří {Kučerík}",
  title="Stability and structural aspects of diketopyrrolopyrrole pigment and its N-alkyl derivatives",
  journal="DYES AND PIGMENTS",
  year="2011",
  volume="89",
  number="1",
  pages="137--143",
  issn="0143-7208"
}