Aryl-substituted unsymmetrical benzothiadiazoles: synthesis, structure, and properties
Rajneesh Misra1, Prabhat Gautam, Shaikh M Mobin
1Department of Chemistry, Indian Institute of Technology Indore , Indore 452 017, India.
Abstract:
A family of unsymmetrical donor-acceptor, ferrocenyl-substituted benzothiadiazoles of types D1-π-A-π-D2, D1-π-A1-π-A2, D1-A-π-D2, and D1-A1-A2-D2, bearing a variety of electron-donating and electron-withdrawing groups, were designed and synthesized. Their photophysical, electrochemical, and computational properties were explored, which show strong donor-acceptor interaction. The presence of electron-rich units anthracene (6f) and triphenylamine (6h), and an electron-deficient unit 1,1,4,4-tetracyanobuta-1,3-diene (TCBD) (9b) results in lowering of the band gap, which leads to a red shift of the absorption spectrum in these benzothiadiazole systems. The single crystal structures of 6c, 6g, 7a, and 7b are reported, which show marvelous supramolecular interactions.
More Related Videos
05:34Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
09:58Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
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,...
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...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Nomenclature of Aromatic Compounds with a Single Substituent
Structure of Benzene: Kekulé Model
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.
Diazonium Group Substitution: –OH and –H
