<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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| Format: | Article |
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MDPI AG
2021-11-01
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| Series: | Chemistry Proceedings |
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| Online Access: | https://www.mdpi.com/2673-4583/8/1/87 |
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| author | Valentina Ferraro Matteo Girotto Marco Bortoluzzi |
| author_facet | Valentina Ferraro Matteo Girotto Marco Bortoluzzi |
| author_sort | Valentina Ferraro |
| collection | DOAJ |
| description | <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. |
| first_indexed | 2024-03-11T06:46:03Z |
| format | Article |
| id | doaj.art-c7f8f71a37ca427287f2276809a08b3a |
| institution | Directory Open Access Journal |
| issn | 2673-4583 |
| language | English |
| last_indexed | 2024-03-11T06:46:03Z |
| publishDate | 2021-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Chemistry Proceedings |
| spelling | doaj.art-c7f8f71a37ca427287f2276809a08b3a2023-11-17T10:19:14ZengMDPI AGChemistry Proceedings2673-45832021-11-01818710.3390/ecsoc-25-11658<i>N</i>,<i>N</i>-Dimethyl-4-amino-2,1,3-benzothiadiazole: Synthesis and Luminescent SolvatochromismValentina Ferraro0Matteo Girotto1Marco Bortoluzzi2Dipartimento di Scienze Molecolari e Nanosistemi, Università Ca’ Foscari Venezia, Via Torino 155, 30170 Mestre, VE, ItalyDipartimento di Scienze Molecolari e Nanosistemi, Università Ca’ Foscari Venezia, Via Torino 155, 30170 Mestre, VE, ItalyDipartimento di Scienze Molecolari e Nanosistemi, Università Ca’ Foscari Venezia, Via Torino 155, 30170 Mestre, VE, Italy<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.https://www.mdpi.com/2673-4583/8/1/87<i>N</i>,<i>N</i>-dimethyl-4-amino-2,1,3-benzothiadiazolefluorescencesolvatochromism2,1,3-benzothiadiazole |
| spellingShingle | Valentina Ferraro Matteo Girotto Marco Bortoluzzi <i>N</i>,<i>N</i>-Dimethyl-4-amino-2,1,3-benzothiadiazole: Synthesis and Luminescent Solvatochromism Chemistry Proceedings <i>N</i>,<i>N</i>-dimethyl-4-amino-2,1,3-benzothiadiazole fluorescence solvatochromism 2,1,3-benzothiadiazole |
| title | <i>N</i>,<i>N</i>-Dimethyl-4-amino-2,1,3-benzothiadiazole: Synthesis and Luminescent Solvatochromism |
| title_full | <i>N</i>,<i>N</i>-Dimethyl-4-amino-2,1,3-benzothiadiazole: Synthesis and Luminescent Solvatochromism |
| title_fullStr | <i>N</i>,<i>N</i>-Dimethyl-4-amino-2,1,3-benzothiadiazole: Synthesis and Luminescent Solvatochromism |
| title_full_unstemmed | <i>N</i>,<i>N</i>-Dimethyl-4-amino-2,1,3-benzothiadiazole: Synthesis and Luminescent Solvatochromism |
| title_short | <i>N</i>,<i>N</i>-Dimethyl-4-amino-2,1,3-benzothiadiazole: Synthesis and Luminescent Solvatochromism |
| title_sort | i n i i n i dimethyl 4 amino 2 1 3 benzothiadiazole synthesis and luminescent solvatochromism |
| topic | <i>N</i>,<i>N</i>-dimethyl-4-amino-2,1,3-benzothiadiazole fluorescence solvatochromism 2,1,3-benzothiadiazole |
| url | https://www.mdpi.com/2673-4583/8/1/87 |
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