Related Experiment Video
Updated: May 8, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Substituent-Controlled Design of Naphthalene Diimide-Based Materials Exhibiting Semiconducting Behavior
Sk S Ahamed1, Nargis Khatun2, Suman K Ghosh3
1Department of Chemistry, Jadavpur University, Kolkata, India.
Abstract:
This work introduces five core 2,6-diaryl-substituted naphthalene diimide (NDI) derivatives accessed through Suzuki-Miyaura cross-coupling, employing imide-functionalized NDIs bearing 2-ethylhexyl side chains. The strategic incorporation of electron-donating and electron-withdrawing aryl groups at the 2,6-positions of the electron-deficient NDI core enabled systematic tuning of the electronic and optical properties of NDI derivatives. UV-Vis absorption studies showed the development of Q-bands and bathochromic shifts, depending on the electronic properties of the substituents, which are essential for optimizing optoelectronic functionality. The experimental observations were further supported by density functional theory calculations, offering deeper insight into the extent of electronic delocalization and the spatial distribution of the frontier molecular orbitals. The semiconducting behavior of all five compounds has been evaluated by fabricating them into Schottky diode devices. With different charge transport properties connected to the electronic characteristics of the core substituents, the resultant devices showed distinct structure-property correlations. Core-engineered NDIs are proven to be adaptable soft materials for tunable organic electronic applications in this study.
Related Concept Videos
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between the...
Directing Effect of Substituents: meta-Directing Groups
Diazonium Group Substitution: –OH and –H
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

