Synthesis, characterization, and DFT study of polycyclic aromatic hydrocarbon precursors, 1,4-diiodo-2,3,5,6-tetraarylbenzene and 1,4-bis(4-bromophenyl)-2,3,5,6-tetraarylbenzene

Siddappa A. Patil, Chananate Uthaisar, Veronica Barone, Bradley D. Fahlman

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

The molecular structure and spectroscopic properties of 1,4-diiodo-2,3,5,6-tetraarylbenzene and 1,4-bis(4-bromophenyl)-2,3,5,6- tetraarylbenzene have been investigated by density functional theory (DFT), 1H NMR, 13C NMR, IR spectroscopy, and elemental analysis. These compounds are the precursors for the synthesis of large polycyclic aromatic hydrocarbons (PAHs). Because of the flexibility of aliphatic chains, DFT calculations of 13C NMR chemical shifts were only calculated in the aromatic region by introducing H atoms replacing the aliphatic chains and 1H NMR chemical shifts were neglected. A drawback of excluding aliphatic chains in the IR calculation was the loss of vibrational modes for C-H stretching and bending. Due to this significant loss of information, the aliphatic chains were included in the IR calculations. The comparison of the calculated 13C NMR and IR parameters with the experimental spectroscopic data reveals good agreement and thus confirmed the suggested molecular structures. In addition, the electronic structure of these compounds was discussed based on HOMO-LUMO analyses.

Original languageEnglish
Pages (from-to)41-47
Number of pages7
JournalJournal of Molecular Structure
Volume1032
DOIs
StatePublished - Jan 30 2013

Keywords

  • 1,4-Bis(4-bromophenyl)-2,3,5,6- tetraarylbenzene
  • 1,4-Diiodo-2,3,5,6-tetraarylbenzene
  • NMR
  • Polycyclic aromatic hydrocarbons
  • Spectroscopic characterization
  • Synthesis

Fingerprint

Dive into the research topics of 'Synthesis, characterization, and DFT study of polycyclic aromatic hydrocarbon precursors, 1,4-diiodo-2,3,5,6-tetraarylbenzene and 1,4-bis(4-bromophenyl)-2,3,5,6-tetraarylbenzene'. Together they form a unique fingerprint.

Cite this