Structures and properties of 1,7-disubstituted perylene tetracarboxylic diimides: The substitutional effect study based on density functional theory calculations

Baolong Liang, Yuexing Zhang, Yanfeng Wang, Wei Xu, Xiyou Li*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

27 Scopus citations

Abstract

Density functional theory (DFT) calculations were carried out to describe the molecular structures, molecular orbitals, atomic charges, UV-vis absorption and IR spectra of 1,7-disubstituted-perylene-3,4;9,10-tetracarboxylic diimide (1,7-disubstituted PDI) with different substituents, namely unsubstituted PDI (PDI-0), 1,7-dimethylthio PDI (S-a), 1,7-dithiophenyl PDI (S-b), 1,7-dimethoxy PDI (O-a), 1,7-diphenoxy PDI (O-b), 1,7-dimethylamino PDI (N-a), 1-methoxy-7-methylthio PDI (OS-a), 1-phenoxy-7-thiophenyl PDI (OS-b), and 1-methoxy-7-methylamino PDI (ON-a). Good consistency was found between the calculated results and experimental data. The substitutional effects of the side groups on both the structure twisting and the electronic absorption spectra depend mainly on the linking atoms rather than the side groups as a whole. The charge distribution, the ionization energy (IE) and electronic affinity (EA) are found to be varied significantly along with the change of the electron donating abilities of the side groups. The effects of the side groups on the vibration spectra of these compounds are also discussed based on both the simulated and experimental results. The present work, representing the first systemic DFT study on the PDI derivatives, sheds further light on clearly understanding structure and spectroscopic properties of PDI compounds.

Original languageEnglish (US)
Pages (from-to)133-141
Number of pages9
JournalJournal of Molecular Structure
Volume917
Issue number2-3
DOIs
StatePublished - Jan 15 2009

Keywords

  • DFT calculation
  • Electronic absorption spectra
  • IR spectra
  • Perylene tetracarboxylic diimide
  • Substitutional effect

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

Fingerprint Dive into the research topics of 'Structures and properties of 1,7-disubstituted perylene tetracarboxylic diimides: The substitutional effect study based on density functional theory calculations'. Together they form a unique fingerprint.

Cite this