2,1,3-Benzothiadiazole Small Donor Molecules: A DFT Study, Synthesis, and Optoelectronic Properties

Zając, Dorota; Honisz, Damian; Łapkowski, Mieczysław; Sołoducho, Jadwiga

doi:10.3390/molecules26051216

Cited by 12 publications

(14 citation statements)

References 46 publications

(39 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[11,12] Incorporation of BT and its derivatives in conjugated polymers or small molecules for optoelectronics [2,13] are advantageous owing to their planar structure, good solubility in organic solvents, strong electron-withdrawing character. [8,[14][15][16] Their narrow optical band gaps and deeper HOMO levels favor efficient electron transfer [1,2] and improve the photovoltaic performances of BHJ solar cells. [2,14,17,18] Hemi-isoindigo acceptors have also been utilized as effective building blocks in designing efficient DÀ A systems because of their desirable structural and electronic features such as excellent planarity, high electron affinity, good solubility in common organic solvents and facile solution processability.…”

Section: Introductionmentioning

confidence: 99%

Functionalized Benzothiadiazole Non‐Fused A−D−A’−D−A Small Molecules for Effective Electron Mobilities and Metal‐free Photocatalysis

Tripathi

Gupta

Sharma

et al. 2023

Chemistry A European J

View full text Add to dashboard Cite

Three non-fused AÀ DÀ A'À DÀ A π-conjugated metalfree small molecules BT-IT1, BT-IBT2 and BT2F-IBT3 have been synthesized and their absorption characteristics and redox properties, as well as charge carrier mobilities have been investigated. The resultant molecules exhibited broad absorption in the range of 325-600 nm in solutions and in thin films the absorption range is 350-700 nm. These new conjugated small molecules showed low-lying HOMO energy levels (À 5.49 to À 5.50 eV), deep LUMO energy levels (À 3.67 to À 3.69 eV) and narrow bandgaps of (E g CV ) ~0.79 eV. Appreciable electron mobilities for compounds BT-IBT2 and BT2F-IBT3 were 4.56 × 10 À 3 and 1.12 × 10 À 3 cm 2 V À 1 s À 1 , respectively, obtained by space-charge limited current (SCLC) measurements. Additionally, excellent photocatalytic performances of BT-2T (6), BT2F-2T (10), BT-IT1, BT-IBT2 and BT2F-IBT3 for highly selective oxidation of thioanisole to desired sulfoxides under visible light irradiation were observed.

show abstract

Section: Introductionmentioning

confidence: 99%

Functionalized Benzothiadiazole Non‐Fused A−D−A’−D−A Small Molecules for Effective Electron Mobilities and Metal‐free Photocatalysis

Tripathi

Gupta

Sharma

et al. 2023

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…According to the literature, − both polyfluorene (PF) and polybenzothiadiazole (PBTH) are unique conjugated polymers that possessed superior fluorescence properties and both chemical and thermal stabilities. We recorded quantum yields of P2, P4, and P5 in both organic solvent (THF) and water, respectively.…”

Section: Results and Discussionmentioning

confidence: 99%

Structural Polyfluorene Derivative Nanocarriers with Promising Fluorescence Emission and Antifouling Properties

Zhu

Zhang

et al. 2022

ACS Appl. Polym. Mater.

View full text Add to dashboard Cite

Herein, a zwitterionic PF-based copolymer, polyfluorene-a-polybenzothiadiazole-g-polycaprolactone-b-poly[3dimethyl(methacryloxyethyl)-propaneammoniumsulfonate] [PF-a-PBTH-g-(PCL-b-PDMAPS)], was synthesized by combining multiple polymerization techniques and further quaternization. The resultant copolymer with optimized structures (P5) was able to form stabilized unimolecular micelles in an aqueous solution with a diameter of approximately 110 nm. The unique donor− acceptor structure between fluorene and benzothiadiazole group along the conjugated main chains endows copolymers with yellowgreen fluorescence, while the PDMAPS chains with a unique zwitterionic nature enabled not only to enhance water solubility, drug loading efficiency (DLE), and drug loading capacity (DLC) of the whole copolymers but also to present promising antifouling property by preventing nonspecific protein/bacteria adhesion. Further in vivo and in vitro experiments demonstrate that the resultant P5 micelles also present lower cytotoxicity and efficient cellular uptake with the incubation of HeLa and HUVEC cells, which tends to prolong the circulation time of drugs. Our work not only provides a rational combination of zwitterions and polyfluorenes to significantly enhance the water solubility of hydrophobic fluorophores but also exhibits the potential of promising bioimaging for dual stimuli-responsive micelles in vitro (simulated body fluids) and in vivo (open).

show abstract

“…All chemicals were used without any further purification. 4,7‐bis(5‐(pyridin‐2‐yl)thiophen‐2‐yl)benzo[c][1,2,5]thiadiazole (TBT) was synthesized by some of us in Wrocław University of Science and Technology, Poland [20].…”

Section: Methodsmentioning

confidence: 99%

Application of a Thiadiazole‐derivative in a Tyrosinase‐based Amperometric Biosensor for Epinephrine Detection

et al. 2021

Self Cite

View full text Add to dashboard Cite

Enzyme-based amperometric biosensors are proving to be important analytical tools in several fields such as food, environmental and, in recent years, the biomedical one. This work describes the use of 4,7-bis(5-(pyridin-2-yl)thiophen-2-yl)benzo [c][1,2,5]thiadiazole (TBT) in the development of a tyrosinase-based biosensor for epinephrine detection. The modifying agent was obtained as a film by electrochemical oxidation of TBT on a gold disk electrode. Electrochemical characterization and scanning electrode microscopy (SEM) images suggest the formation of a conducting film on the electrode surface. Tyrosinase from mushroom was then immobilized by a mixed technique of adsorption and cross-linking. Glutaraldehyde was used as a coupling agent. The obtained device shows a very good linear response (0.1-50 μM) with a LoD value of 0.06 μM and a LoQ of 0.09 μM. Moreover, good selectivity towards some typical interferents (namely, ascorbic acid, tryptophan, uric acid and L-cysteine) and satisfactory recoveries have been observed.

show abstract

2,1,3-Benzothiadiazole Small Donor Molecules: A DFT Study, Synthesis, and Optoelectronic Properties

Cited by 12 publications

References 46 publications

Functionalized Benzothiadiazole Non‐Fused A−D−A’−D−A Small Molecules for Effective Electron Mobilities and Metal‐free Photocatalysis

Functionalized Benzothiadiazole Non‐Fused A−D−A’−D−A Small Molecules for Effective Electron Mobilities and Metal‐free Photocatalysis

Structural Polyfluorene Derivative Nanocarriers with Promising Fluorescence Emission and Antifouling Properties

Application of a Thiadiazole‐derivative in a Tyrosinase‐based Amperometric Biosensor for Epinephrine Detection

Contact Info

Product

Resources

About