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Six novel benzimidazole-based D-π-A compounds 4 a-4 f were concisely synthesized by attaching different donor/acceptor units to the skeleton of 1,3-bis(1H-benzimidazol-2-yl)benzene on its 5-position through an ethynyl link. Due to the twisted conformation and effective conjugation structure, these dual-state emission (DSE) molecules show intense and multifarious photoluminescence, and their fluorescence quantum yields in solution and solid state can be up to 96.16 and 69.82 %, respectively. Especially, for excellent photostability, obvious solvatofluorochromic and extraordinary wide range of solvent compatibility, DSE molecule 4 a is a multifunctional fluorescent probe for the visual detection of nitroaromatic compounds (NACs) with the limit of detection as low as 10 M. The quenching mechanism has been proved as the results of photoinduced electron transfer and fluorescence resonance energy transfer processes. Importantly, probe 4 a can sensitively detect NACs not only in real water samples, but also on 4 a-coated strips and 4 a@PBAT thin films.
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http://dx.doi.org/10.1002/chem.202103478 | DOI Listing |
Luminescence
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.
View Article and Find Full Text PDFLangmuir
September 2025
Advanced Polymer Laboratory, Department of Polymer Science and Technology, Government College of Engineering and Leather Technology (Post Graduate), Maulana Abul Kalam Azad University of Technology, Salt Lake City, Kolkata 700106, West Bengal, India.
This research provides a constructive approach for developing high-performance polymer nanohybrids toward enhancing optoelectronic properties, fluorogenic viscosity sensing, and metal-free electrocatalytic oxidation of glycerol to value-added organic(s). Herein, reduced graphene oxide (RGO) and mildly oxidized RGO (MRGO) are strategically combined with fluorescent electroactive polymers (FEPs) to develop a promising sustainable metal-free electrocatalytic system suitable for amplifying opto-electrochemical properties, multiplatform sensing capacity, and electrocatalytic efficiency. The optimized polymeric counterpart (FEP2) promotes dual-state emission in the supramolecular network of RGO-/MRGO-incorporated fluorescent electroactive hybrid polymers (RFEHPs/MFEHPs) through physicochemically confined atypical electron-rich -C(═O)NH-/-C(═O)O-/-SOH fluorophores of (hydroxyethyl)methacrylate and 2-acrylamido-2-methylpropane-1-sulfonic acid monomers.
View Article and Find Full Text PDFJ Org Chem
September 2025
Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo, Hokkaido 060-0810, Japan.
Stimulus-responsive materials with reversible optical properties are of significant interest for the development of functional systems. Herein, we present the design and synthesis of diazaanthraquinodimethane (NAQD) derivatives incorporating -substituted 4-methoxyphenyl groups. A phenanthrene-fused scaffold was employed to balance conformational flexibility and redox stability, while an substitution strategy was used to control the molecular conformation and near-infrared (NIR) absorption.
View Article and Find Full Text PDFChem Asian J
August 2025
State Key Laboratory for Modification of Chemical Fiber and Polymer Materials, Key Lab of Science and Technology of Eco-Textile, Ministry of Education, College of Chemistry and Chemical Engineering, Donghua University, Shanghai, 201620, China.
Dual-state luminescent materials, which emit strongly in both dispersed and aggregate states, are highly desirable for advanced optoelectronic and sensing applications. In this study, we rationally designed a series of benzimidazole-based donor-π-acceptor (D-π-A) compounds using triphenylamine (TPA) as the donor and benzimidazole as the acceptor, functionalized with flexible alkyl chains to modulate intermolecular packing. Benefitting from their rigid planar molecular conformation, all four compounds exhibit intense blue fluorescence in both solution and the PMMA-doped state.
View Article and Find Full Text PDFOrg Lett
August 2025
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.
We demonstrated the design and photophysical properties of a dual-state emissive π-conjugated dipyridyl-dipyrroethene chromophore () synthesized via selective diformylation of ()-dipyrroethene followed by condensation with 2-amino pyridine. The rational molecular design, incorporating both hydrogen bonding and π···π interactions, leads to a unique supramolecular architecture in the solid state, and the system exhibits aggregation-induced emission properties. We further extend the applicability of chromophore for the selective detection of serum albumin.
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