In this paper, the molecular design of the first deep-lowest unoccupied molecular orbital (LUMO) level diimide π-electron core, benzo[ c]thiophene diimide (BTDI), as a novel n-type organic semiconductor was determined. An original synthetic sequence was devised to obtain the target cyclohexyl-BTDI (Cy-BTDI) derivative. Cy-BTDI demonstrated completely reversible reduction waves and a stable radical anionic state. Favorable brickwork molecular assembly and two-dimensional charge transport properties of Cy-BTDI were exhibited in the solid state. As a result, air-stable electron mobilities were obtained from the BTDI organic field-effect transistors under ambient conditions.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.9b01239 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Accelerating discovery of bioactive ligands with pharmacophore-informed generative models.
Nat Commun
March 2025
Center for Quantitative Biology, Academy for Advanced Interdisciplinary Studies, Peking University, Beijing, China.
Deep generative models have advanced drug discovery but often generate compounds with limited structural novelty, providing constrained inspiration for medicinal chemists. To address this, we develop TransPharmer, a generative model that integrates ligand-based interpretable pharmacophore fingerprints with a generative pre-training transformer (GPT)-based framework for de novo molecule generation. TransPharmer excels in unconditioned distribution learning, de novo generation, and scaffold elaboration under pharmacophoric constraints.
View Article and Find Full Text PDFSynthesis of - and ,-Heterocycle-Dipeptide Conjugates for Supramolecular Hydrogel Formation.
Molecules
February 2025
Centro de Química, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal.
Small peptides with aromatic nuclei at the -terminus have been shown to form bioactive, biocompatible, and biodegradable supramolecular peptide hydrogels. Novel heterocycle-dipeptide conjugates with potential biological activity or application as drug carriers were synthesized by using (benzo[]thiophene) and ,(thieno [2,3-]pyridine and thieno[2,3-]quinoline) heterocycles as -protective groups for dipeptides l-Phe-l-Phe and l-Phe-l-Leu. The synthesis involved coupling heterocyclic carboxylic acids with trifluoroacetate salts of ethyl l-phenylalanyl-l-phenylalaninate and ethyl l-phenylalanyl- l-leucinate using HBTU and EtN, producing the corresponding six -heterocycle-dipeptide ester conjugates, which were then hydrolyzed to the carboxylic acids.
View Article and Find Full Text PDFThree Isomeric Dioctyl Derivatives of 2,7-Dithienyl[1]benzo-thieno[3,2-b][1]benzothiophene: Synthesis, Optical, Thermal, and Semiconductor Properties.
Materials (Basel)
February 2025
Enikolopov Institute of Synthetic Polymeric Materials Russian Academy of Sciences, Profsoyuznaya Str. 70, Moscow 117393, Russia.
Organic semiconductor materials are interesting due to their application in various organic electronics devices. [1]benzothieno[3,2-b][1]benzothiophene (BTBT) is a widely used building block for the creation of such materials. In this work, three novel solution-processable regioisomeric derivatives of BTBT-2,7-bis(3-octylthiophene-2-yl)BTBT (), 2,7-bis(4-octylthiophene-2-yl)BTBT (), and 2,7-bis(5-octylthiophene-2-yl)BTBT ()-were synthesized and investigated.
View Article and Find Full Text PDFDesign, synthesis and biological evaluation of benzo[b]thiophene analogues as novel ferroptosis inhibitor that inhibit fibrosarcoma cell proliferation.
Bioorg Med Chem
April 2025
School of Pharmaceutical Sciences, and Institute of Drug Discovery & Development, Zhengzhou University, 100 Kexue Avenue, Zhengzhou, Henan 450001, China. Electronic address:
While apoptosis activation has traditionally been considered as an anti-cancer mechanism, current research points to ferroptosis stimulation as a potentially effective cancer therapy. Glutathione peroxidase 4 (GPX4), an essential antioxidant enzyme, serves as a negative regulator of ferroptosis, and its targeted inhibition or degradation can efficiently induce this process. In this study, a potent ferroptosis inducer III-4 that bearing a benzo[b]thiophene moiety was developed by employing a sequential structure optimization process based on RSL-3 to inhibit cancer cells proliferation.
View Article and Find Full Text PDFDesign, Synthesis, Biocompatibility, molecular docking and molecular dynamics studies of novel Benzo[b]thiophene-2-carbaldehyde derivatives targeting human IgM Fc Domains.
Bioorg Chem
March 2025
Department of Chemistry, St Berchmans College (Autonomous), Changanassery, Kerala 686101, India; Centre for Theoretical and Computational Chemistry, St Berchmans College (Autonomous), Changanassery, Kerala 686101, India. Electronic address:
In this study, three novel derivatives of benzo[b]thiophene-2-carbaldehyde (BTAP1, BTAP2, and BTAP3) were successfully synthesized and comprehensively characterized using spectroscopic techniques including FTIR, UV-VIS, HNMR, and CNMR. Thermal analysis through TGA and DTA demonstrated remarkable thermal stability with a maximum threshold at 270 °C. Spectroscopic investigations revealed π → π* transitions in all compounds, attributed to the conjugated system comprising benzothiophene rings connected to bromophenyl/ aminophenyl/phenol rings via α, β-unsaturated ketone bridges.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!