Next Article in Journal
Can Eucalyptol Replace Antibiotics?
Next Article in Special Issue
A Comprehensive Analysis of the Metal–Nitrile Bonding in an Organo-Diiron System
Previous Article in Journal
Synthesis and In Vitro Characterization of Glycopeptide Drug Candidates Related to PACAP1–23
Previous Article in Special Issue
Facile N9-Alkylation of Xanthine Derivatives and Their Use as Precursors for N-Heterocyclic Carbene Complexes
 
 
Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
Journals
Molecules
Volume 26
Issue 16
10.3390/molecules26164931
molecules-logo
Submit to this Journal Review for this Journal Propose a Special Issue
► Article Menu

Article Menu

share Share announcement Help format_quote Cite question_answer Discuss in SciProfiles
first_page
settings
Order Article Reprints
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Article

Benzothiadiazole vs. iso-Benzothiadiazole: Synthesis, Electrochemical and Optical Properties of D–A–D Conjugated Molecules Based on Them

by
Nikita S. Gudim
1,
Ekaterina A. Knyazeva
1,2,
Ludmila V. Mikhalchenko
1,
Ivan S. Golovanov
1,
Vadim V. Popov
2,
Natalia V. Obruchnikova
1 and
Oleg A. Rakitin
1,2,*
1
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russia
2
Nanotechnology Education and Research Center, South Ural State University, 454080 Chelyabinsk, Russia
*
Author to whom correspondence should be addressed.
Molecules 2021, 26(16), 4931; https://doi.org/10.3390/molecules26164931
Submission received: 19 July 2021 / Revised: 10 August 2021 / Accepted: 11 August 2021 / Published: 14 August 2021
(This article belongs to the Special Issue Advances in Organometallic Chemistry—Papers of the Editorial Board Members (EBMs))
Browse Figures
Versions Notes

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.
Keywords: 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 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

Share and Cite

MDPI and ACS Style

Gudim, N.S.; Knyazeva, E.A.; Mikhalchenko, L.V.; Golovanov, I.S.; Popov, V.V.; Obruchnikova, N.V.; Rakitin, O.A. Benzothiadiazole vs. iso-Benzothiadiazole: Synthesis, Electrochemical and Optical Properties of D–A–D Conjugated Molecules Based on Them. Molecules 2021, 26, 4931. https://doi.org/10.3390/molecules26164931

AMA Style

Gudim NS, Knyazeva EA, Mikhalchenko LV, Golovanov IS, Popov VV, Obruchnikova NV, Rakitin OA. Benzothiadiazole vs. iso-Benzothiadiazole: Synthesis, Electrochemical and Optical Properties of D–A–D Conjugated Molecules Based on Them. Molecules. 2021; 26(16):4931. https://doi.org/10.3390/molecules26164931

Chicago/Turabian Style

Gudim, Nikita S., Ekaterina A. Knyazeva, Ludmila V. Mikhalchenko, Ivan S. Golovanov, Vadim V. Popov, Natalia V. Obruchnikova, and Oleg A. Rakitin. 2021. "Benzothiadiazole vs. iso-Benzothiadiazole: Synthesis, Electrochemical and Optical Properties of D–A–D Conjugated Molecules Based on Them" Molecules 26, no. 16: 4931. https://doi.org/10.3390/molecules26164931

APA Style

Gudim, N. S., Knyazeva, E. A., Mikhalchenko, L. V., Golovanov, I. S., Popov, V. V., Obruchnikova, N. V., & Rakitin, O. A. (2021). Benzothiadiazole vs. iso-Benzothiadiazole: Synthesis, Electrochemical and Optical Properties of D–A–D Conjugated Molecules Based on Them. Molecules, 26(16), 4931. https://doi.org/10.3390/molecules26164931

Article Metrics

Back to TopTop