Halogen-bonded supramolecular assemblies based on phenylethynyl pyridine derivatives

driving crystal packing through systematic chemical modifications

Tanya Shirman, Jean Francois Lamere, Linda J W Shimon, Tarkeshwar Gupta, Jan M L Martin, Milko van der Boom

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

A series of phenylethynyl pyridine derivatives 1-4 possessing both perfluorocarbon (PFC) and hydrocarbon (HC) moieties have been synthesized and used for the formation of halogen bonding (XB)-based networks. X-ray crystal structure analyses indicate the dominance of XB synthons, which represent the one-dimensional (ID) structure directing interaction, leading to the formation of supramolecular chains. The influence of structural/electronic factors (e.g., electron donor/acceptor strength, sterically demanding substituents) on XB formation of compounds 1-4 have been compared with structurally related stilbazole systems (I, II). The XB-bonded networks are formed in collaboration with other noncovalent interactions such as π-π stacking, hydrogen bonding, C-H⋯F and F⋯F. Molecular electrostatic potentials and atomic polar tensor (APT) charges of the donor and acceptor sites have been determined by density functional theory (DFT) calculations.

Original languageEnglish
Pages (from-to)3066-3072
Number of pages7
JournalCrystal Growth and Design
Volume8
Issue number8
DOIs
Publication statusPublished - Aug 2008

Fingerprint

Fluorocarbons
Halogens
Chemical modification
Hydrocarbons
Pyridine
halogens
assemblies
Density functional theory
Tensors
Electrostatics
pyridines
Hydrogen bonds
Crystal structure
Derivatives
X rays
Crystals
Electrons
crystals
hydrocarbons
interactions

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)
  • Condensed Matter Physics

Cite this

Halogen-bonded supramolecular assemblies based on phenylethynyl pyridine derivatives : driving crystal packing through systematic chemical modifications. / Shirman, Tanya; Lamere, Jean Francois; Shimon, Linda J W; Gupta, Tarkeshwar; Martin, Jan M L; van der Boom, Milko.

In: Crystal Growth and Design, Vol. 8, No. 8, 08.2008, p. 3066-3072.

Research output: Contribution to journalArticle

Shirman, Tanya ; Lamere, Jean Francois ; Shimon, Linda J W ; Gupta, Tarkeshwar ; Martin, Jan M L ; van der Boom, Milko. / Halogen-bonded supramolecular assemblies based on phenylethynyl pyridine derivatives : driving crystal packing through systematic chemical modifications. In: Crystal Growth and Design. 2008 ; Vol. 8, No. 8. pp. 3066-3072.
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