Crystallographic insights into the structural aspects of thioctic acid based halogen-bond donor for the functionalization of gold nanoparticles

Kavitha Buntara Sanjeeva, Ilaria Tirotta, Vijith Kumar, Francesca Baldelli Bombelli*, Giancarlo Terraneo, Pierangelo Metrangolo

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

3 Citations (Scopus)

Abstract

The synthesis and self-assembly capabilities of a new halogen-bond donor ligand, 2,3,5,6-tetrafluoro-4-iodophenyl 5-(1,2-dithiolan-3-yl)pentanoate (1), are reported. The crystal structure of ligand (1) and the formation of a cocrystal with 1,2-di(4-pyridyl)ethylene, (1)·(2), both show halogen bonds involving the 4-iodotetrafluorobenzene moiety. Ligand (1), being a self-complementary unit, forms an infinite halogen-bonded chain driven by the S...I synthon, while the cocrystal (1)·(2) self-assembles into a discrete trimeric entity driven by the N...I synthon. Ligand (1) was also successfully used to functionalize the surface of gold nanoparticles, AuNP-(1). Experiments on the dispersibility profile of AuNP-(1) demonstrated the potential of halogen bonding in facilitating the dispersion of modified NPs with halogen-bond donors in pyridine. The aim of this research is to perform a complete structural description of a new halogen bonding (XB) donor, which will be used for the surface functionalization of gold nanoparticles (AuNPs). Crystallographic studies of simple model systems will be used to determine the recognition capabilities of the synthesized XB donor, and the functionalization of the AuNPs with the XB donor and their solubility profile in different solvents will be described.

Original languageEnglish
Pages (from-to)240-246
Number of pages7
JournalACTA CRYSTALLOGRAPHICA SECTION B : STRUCTURAL SCIENCE, CRYSTAL ENGINEERING AND MATERIALS
Volume73
Issue number2
DOIs
Publication statusPublished - 1 Apr 2017
MoE publication typeA1 Journal article-refereed

Keywords

  • gold nanoparticles
  • halogen bonding
  • self-assembly
  • surface functionalization

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