Publication detail

Structure and Raman spectra of pyridyl substituted diketo-pyrrolo-pyrrole isomers and polymorphs

LUŇÁK, S. VYŇUCHAL, J. HORÁČKOVÁ, P. FRUMAROVÁ, B. ŽÁK, Z. KUČERÍK, J. SALYK, O.

Original Title

Type

journal article - other

Language

English

Original Abstract

A complete series of symmetrical and unsymmetrical isomeric pairs of 4- and 2-pyridyl substituted diketo-pyrrolo-pyrroles was synthesized. Both polymorphs of 3,6-bis-(40-pyridyl)-2,5-dihydro-pyrrolo [3,4-c]pyrrole-1,4-dione were prepared. Asymmetrical 3-phenyl-6-pyridine-20-yl-2,5-dihydro-pyrrolo [3,4-c]pyrrole-1,4-dione was synthesized for the first time and X-ray structure of its monocrystal was determined. Density functional theory calculations of the ground state geometry were compared with experimental X-ray diffraction data. Theoretical Raman spectra enabled to assign the main peaks of the experimental ones for all four pyridyl DPP derivatives. Crucial spectral features, which reflect the molecular and crystal (H-bond invoked) asymmetry are C@O (pyrrolinone) stretching, NAH (pyrrolinone) bending and trigonal (hetero)aryl bending. Sublimation temperatures of 2-pyridyl derivatives are significantly lower than for 4-pyridyl derivatives, in which stronger in-plane NH(pyrrolinone) ACO(pyrrolinone) intermolecular H-bonding dominates.

Keywords

Diketo-pyrrolo-pyrrole Density functional theory Raman spectra

Authors

LUŇÁK, S.; VYŇUCHAL, J.; HORÁČKOVÁ, P.; FRUMAROVÁ, B.; ŽÁK, Z.; KUČERÍK, J.; SALYK, O.

RIV year

2010

Released

21. 8. 2010

Publisher

Elsevier

ISBN

0022-2860

Periodical

JOURNAL OF MOLECULAR STRUCTURE

Year of study

983

Number

1-3

State

Kingdom of the Netherlands

Pages from

Pages to

Pages count

BibTex

@article{BUT50530,
  author="Stanislav {Luňák} and Jan {Vyňuchal} and Pavlína {Horáčková} and Božena {Frumarová} and Zdirad {Žák} and Jiří {Kučerík} and Ota {Salyk}",
  title="Structure and Raman spectra of pyridyl substituted diketo-pyrrolo-pyrrole isomers and polymorphs",
  journal="JOURNAL OF MOLECULAR STRUCTURE",
  year="2010",
  volume="983",
  number="1-3",
  pages="39--47",
  issn="0022-2860"
}