<i>N</i>,<i>N</i>-Dimethyl-4-amino-2,1,3-benzothiadiazole: Synthesis and Luminescent Solvatochromism

<i>N</i>,<i>N</i>-Dimethyl-4-amino-2,1,3-benzothiadiazole: Synthesis and Luminescent Solvatochromism

<i>N</i>,<i>N</i>-Dimethyl-4-amino-2,1,3-benzothiadiazole (BTD<sup>NMe2</sup>) was synthesized from the commercially available 2,1,3-benzothiadiazole (BTD) by nitration in a sulfonitric mixture, followed by a reduction of the nitro group and subsequent methylation...

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Bibliographic Details
Main Authors:	Valentina Ferraro, Matteo Girotto, Marco Bortoluzzi
Format:	Article
Language:	English
Published:	MDPI AG 2021-11-01
Series:	Chemistry Proceedings
Subjects:	<i>N</i>,<i>N</i>-dimethyl-4-amino-2,1,3-benzothiadiazole fluorescence solvatochromism 2,1,3-benzothiadiazole
Online Access:	https://www.mdpi.com/2673-4583/8/1/87

Description
Summary:	<i>N</i>,<i>N</i>-Dimethyl-4-amino-2,1,3-benzothiadiazole (BTD<sup>NMe2</sup>) was synthesized from the commercially available 2,1,3-benzothiadiazole (BTD) by nitration in a sulfonitric mixture, followed by a reduction of the nitro group and subsequent methylation with iodomethane. BTD<sup>NMe2</sup> was fully characterized by means of nuclear magnetic resonance (NMR) and infrared spectroscopy. The solutions of BTD<sup>NMe2</sup> in common organic solvents revealed to be appreciably luminescent in the visible range. The electronic transitions related to the absorption and emission properties were associated with the HOMO–LUMO energy gap by means of electrochemical measurements and DFT calculations. Finally, BTD<sup>NMe2</sup> was successfully used to prepare luminescent-doped poly(methyl methacrylate) samples.
ISSN:	2673-4583