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Benzothiadiazole vs. iso-Benzothiadiazole: Synthesis, Electrochemical and Optical Properties of D–A–D Conjugated Molecules Based on Them
Benzothiadiazole vs. iso-Benzothiadiazole: Synthesis, Electrochemical and Optical Properties of D–A–D Conjugated Molecules Based on Them
- Source :
- Molecules, Volume 26, Issue 16, Molecules, Vol 26, Iss 4931, p 4931 (2021)
- Publication Year :
- 2021
- Publisher :
- MDPI AG, 2021.
-
Abstract
- 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 ELUMO and energy band gap (Eg), 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.
- Subjects :
- optical properties
Materials science
Band gap
Organic Chemistry
Pharmaceutical Science
π-spacer–acceptor–π-spacer type structures
electrochemical properties
Conjugated system
Acceptor
Coupling reaction
Analytical Chemistry
Stille reaction
benzo[d][1,2,3]thiadiazole
QD241-441
cross-coupling reactions
Chemistry (miscellaneous)
Excited state
Drug Discovery
Molecular Medicine
Physical chemistry
Molecule
Physical and Theoretical Chemistry
Luminescence
benzo[c][1,2,5]thiadiazole
Subjects
Details
- ISSN :
- 14203049
- Volume :
- 26
- Database :
- OpenAIRE
- Journal :
- Molecules
- Accession number :
- edsair.doi.dedup.....9a439439af93522b1235b5c625eb7bb6
- Full Text :
- https://doi.org/10.3390/molecules26164931