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Benzothiadiazole vs. iso-Benzothiadiazole: Synthesis, Electrochemical and Optical Properties of D–A–D Conjugated Molecules Based on Them
| Content Provider | MDPI |
|---|---|
| Author | Gudim, Nikita S. Knyazeva, Ekaterina A. Mikhalchenko, Ludmila V. Golovanov, Ivan S. Popov, Vadim V. Obruchnikova, Natalia V. Rakitin, Oleg A. |
| Copyright Year | 2021 |
| Description | This paper presents an improved synthesis of 4,7-dibromobenzo[d][1,2,3]thiadiazole from commercially available reagents. According to quantum-mechanical calculations, benzo[d][1,2,3]thiadiazole (isoBTD) has higher values of $E_{LUMO}$ and energy band gap $(E_{g}$), which indicates high electron conductivity, occurring due to the high stability of the molecule in the excited state. We studied the cross-coupling reactions of this dibromide and found that the highest yields of π-spacer–acceptor–π-spacer type compounds were obtained by means of the Stille reaction. Therefore, 6 new structures of this type have been synthesized. A detailed study of the optical and electrochemical properties of the obtained π-spacer–acceptor–π-spacer type compounds in comparison with isomeric structures based on benzo[c][1,2,5]thiadiazole (BTD) showed a red shift of absorption maxima with lower absorptive and luminescent capacity. However, the addition of the 2,2′-bithiophene fragment as a π-spacer resulted in an unexpected increase of the extinction coefficient in the UV/vis spectra along with a blue shift of both absorption maxima for the isoBTD-based compound as compared to the BTD-based compound. Thus, a thorough selection of components in the designing of appropriate compounds with benzo[d][1,2,3]thiadiazole as an internal acceptor can lead to promising photovoltaic materials. |
| Starting Page | 4931 |
| e-ISSN | 14203049 |
| DOI | 10.3390/molecules26164931 |
| Journal | Molecules |
| Issue Number | 16 |
| Volume Number | 26 |
| Language | English |
| Publisher | MDPI |
| Publisher Date | 2021-08-14 |
| Access Restriction | Open |
| Subject Keyword | Molecules Benzo[d][1,2,3]thiadiazole Benzo[c][1,2,5]thiadiazole Π-spacer–acceptor–π-spacer Type Structures Cross-coupling Reactions Optical Properties Electrochemical Properties |
| Content Type | Text |
| Resource Type | Article |
