Related Experiment Video
Updated: Jun 25, 2026

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
Published on: February 7, 2017
Substituent effect on the electronic properties and morphologies of self-assembling bisphenazine derivatives
Kelly K McGrath1, Kyoungmi Jang, Kathleen A Robins
1Department of Chemistry, University of Nevada Las Vegas, 4505 Maryland Parkway, Box 454003, Las Vegas, Nevada 89154-4003, USA.
Abstract:
Tuning electronic properties and morphologies: We report a unique design platform of n-type organic semiconductors based on asymmetrically substituted bisphenazines that enable tuning of both electronic properties and morphologies of 1D nanostructures (see figure) by using small substituents with various sizes and electronic demands.This paper reports the synthesis and characterization of novel self-assembling n-type organic semiconductors based on asymmetrically substituted bisphenazines with various functional groups of different size, electron-withdrawing ability, and conjugation length. The overarching objective of this research is to tune electronic properties and morphologies of self-assembled structures of this system simultaneously, which offers a potentially useful platform for future optoelectronic applications. The thermal, optical, and electrochemical properties associated with different substituents were studied by differential scanning calorimetry (DSC), UV-visible and fluorescence spectroscopy, and cyclic voltammetry (CV). Electronic properties were calculated using density functional theory, and results were compared to experimental HOMO, LUMO, and energy gaps. The one-dimensional (1D) self-assembly properties of these new n-type molecules are discussed in terms of the type of peripheral substituents, alkyl side group length, and assembly conditions. This study includes extensive investigations by scanning electron microscopy (SEM) and X-ray diffraction (XRD).
Related Concept Videos
Directing and Steric Effects in Disubstituted Benzene Derivatives
Nomenclature of Aromatic Compounds with Multiple Substituents
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
Directing Effect of Substituents: meta-Directing Groups
Nomenclature of Aromatic Compounds with a Single Substituent
Directing Effect of Substituents: ortho–para-Directing Groups
Stability of Substituted Cyclohexanes
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...

