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The title compound, C58H64S8, has been prepared by Pd-catalysed direct C-H arylation of tetrathienonaphthalene (TTN) with 5-hexyl-2-iodothiophene and recrystallized by slow evaporation from dichloromethane. The crystal structure shows a completely planar geometry of the TTN core, crystallizing in the monoclinic space group P2(1)/c. The structure consists of slipped π-stacks and the interfacial distance between the mean planes of the TTN cores is 3.456 (5) Å, which is slightly larger than that of the comparable derivative of tetrathienoanthracene (TTA) with 2-hexylthiophene groups. The packing in the two structures is greatly influenced by both the aromatic core of the structure and the alkyl side chains.
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http://dx.doi.org/10.1107/S0108270113010895 | DOI Listing |
Org Biomol Chem
September 2025
Organic and Medicinal Chemistry Research Laboratory, School of Advanced Sciences, Vellore Institute of Technology, Vellore-632 014, Tamil Nadu, India.
An efficient synthesis and late-stage C-H functionalization of papaverine under volatile solvent-free conditions are reported. This methodology demonstrates significant potential for applications in the active pharmaceutical ingredient (API) industry, particularly for the sustainable and solvent-free synthesis of papaverine. A plausible reaction mechanism was meticulously elucidated through comprehensive control experiments.
View Article and Find Full Text PDFChem Rec
September 2025
LAQV, REQUIMTE Department of Chemistry, University of Aveiro Campus de Campus de Santiago, Aveiro, 3810-193, Portugal.
The aim of the present review is to provide a systematic survey on the recent advancements in the chemical synthesis of thiochromones, thiochromanones, the less explored thiochromene-4-thiones and some analogs. These compounds are used as versatile building blocks in the synthesis of other complex and polycyclic heterocyclic analogs. Highlights on biological and photophysical properties of these thio derivatives are also included and discussed.
View Article and Find Full Text PDFJ Mater Chem B
September 2025
Dipartimento di Chimica "Giacomo Ciamician", Alma Mater Studiorum - Università di Bologna, Via Piero Gobetti, 85, Bologna 40129, Italy.
Donor-acceptor-donor (D-A-D) thiophene-based compounds, characterized by thiophene as a donor unit and benzothiadiazole (Bz) as an acceptor, represent an emerging class of theranostic agents for imaging and photodynamic therapy. Here, we expand this class of molecules by strategically varying the position of the electron-accepting unit within the oligothiophene (OT) backbone structure, realizing a series of different push-pull architectures (A-D, D-A-D, and D-A). This rational design allows for precise modulation of key photophysical parameters, including absorption and emission spectra, molar absorption coefficient, charge separation, and frontier molecular orbitals.
View Article and Find Full Text PDFSmall
September 2025
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati, Assam, 781039, India.
Alzheimer's disease (AD) is a progressive neurodegenerative disorder marked by cognitive decline and the accumulation of amyloid-β (Aβ) plaques, with current treatments offering only limited efficacy. Targeted photo-oxygenation of Aβ using small-molecule photosensitizers has emerged as a promising strategy to modulate amyloid aggregation and mitigate associated toxicity. In this work, the rational design and synthesis of donor-engineered, benzimidazole-functionalized aggregation-induced emission (AIE) photosensitizer with optimized photophysical and morphological properties for multimodal theranostic applications in AD is analyzed and reported.
View Article and Find Full Text PDFLuminescence
September 2025
School of Chemistry, South China Normal University, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, GDMPA Key Laboratory for Process Control and Quality Evaluation of Chiral Pharmaceuticals, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou, C
A series of 2-substituted 4H-chromen-4-ones 3a-3h containing triphenylamine or N-phenylcarbazole on the benzene ring were synthesized for the first time via the Suzuki coupling reaction. The photophysical properties of the compounds and their relationship to the structure of the compounds were investigated by methods such as spectroscopic analysis, single-crystal analysis, and theoretical calculations. The systematic results indicate that compounds 3a-3h have intramolecular charge transfer (ICT), aggregation-induced emission (AIE), and dual-state emission (DSE) effects with a wide range of fluorescence emission wavelengths (421-618 nm), showing the potential to be developed into a full-color fluorophore.
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