Related Experiment Video
Updated: Jun 3, 2026

Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds
Published on: October 18, 2018
Diode-like I-V characteristics of a nonplanar polyaromatic compound: a spectroscopic study of isolated and stacked
Shern-Long Lee1, Min-Jie Huang, Chun-hsien Chen
1Department of Chemistry, National Taiwan University, Taipei 10617, Taiwan.
Abstract:
In this scanning-tunneling-microscopy/spectroscopy study (STM/STS), samples of isolated and close-packed dibenzo[g,p]chrysene (DBC), a nonplanar polyaromatic compound, are used as model systems to demonstrate the effect of intermolecular interactions on the electronic structures. For dropcast films, DBC molecules adopt an edge-on orientation in a close-packed structure on graphite. Isolated DBC molecules are prepared on graphite from a DBC-coated STM tip by a ca. 7 V/10 μs pulse. STS spectra for both isolated- and close-packed DBC molecules exhibit diode-like I-V curves in which the latter shows a turn-on voltage (0.47 V) smaller than that of the former (0.91 V). The diode-like behaviors are attributed to the more-facile tunneling of electrons through the HOMO of DBC than through the LUMO. The reduced turn-on voltage for the films is ascribed to the diminished HOMO-LUMO gap based on the results of DFT (density functional theory) simulations for the energy-level couplings of π-stacked DBC molecules.
Related Concept Videos
Aromatic Hydrocarbon Anions: Structural Overview
Due to the absence of continuous overlap of p...
π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group with both...
Structure of Conjugated Dienes
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
UV–Vis Spectroscopy: Woodward–Fieser Rules
Criteria for Aromaticity and the Hückel 4n + 2 Rule
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as Hückel’s rule or the 4n + 2 rule.

