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The very simple organic molecules have been employed to construct highly efficient single-benzene solid emitters (quantum yields: 0.72-0.84) with crystal lasing properties based on aggregation-induced emission (AIE) generated through an excited-state intramolecular proton transfer (ESIPT) reaction.
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http://dx.doi.org/10.1039/c6cc02616h | DOI Listing |
Nat Commun
July 2025
Department of Materials Science and Engineering, University of Michigan, Ann Arbor, Michigan, USA.
Achieving high quantum yields for organic fluorophores in both solution and in the polycrystalline solid state is a significant yet challenging goal, as most fluorophores typically emit effectively in only one phase. In this study, we introduce 1,1'-(2,5-dimethoxyterephthaloyl)-bis(glutraimide) (TGlu), a novel 'single benzene'-based organic fluorophore featuring an alkoxy donor and an N-acyl-glutarimide acceptor. TGlu achieves close-to-unity fluorescence quantum yields in both solution and in the polycrystalline state.
View Article and Find Full Text PDFChemistry
August 2025
LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, Campus de Santiago, Aveiro, 3810-193, Portugal.
A comprehensive study of a single-benzene fluorophore, characterized by a low molecular weight and a significant Stokes' shift, is reported. The fluorophore exhibits crystallization-induced emission enhancement and pH-dependent luminescence, attributable to a conformational lock in the crystalline state and suppression of nonemissive forms upon deprotonation. Extensive photophysical analysis reveals a quantum yield increase from 1% in solution to 22% in the solid state, along with a consistent emission wavelength irrespective of the state.
View Article and Find Full Text PDFChemistry
March 2025
Faculty of Chemistry (Organic Chemistry), CENIDE and Center of Medical Biotechnology (ZMB), University of Duisburg-Essen, Universitätsstraße 7, 45141, Essen, Germany.
In recent years, researchers studying fluorogenic samples have steadily shifted from using large, expensive, poorly soluble fluorophores with complex synthetic sequences to smaller, simpler π scaffolds with low molecular weight. This research article presents an in-depth study of the photophysical properties of five bridged single-benzene-based fluorophores (SBBFs) investigated for their solution and solid-state emission (SSSE) properties. The compounds O, NO, NO, NO, and N are derived from a central terephthalonitrile core and vary in the amount of oxygen and nitrogen bridging atoms.
View Article and Find Full Text PDFChem Commun (Camb)
August 2024
Department of Chemistry, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, Korea.
The excited-state tautomer equilibrium of the urea-fused single-benzene fluorophore was synthetically modulated to produce exceptionally large Stokes shifts (>12 400 cm). The key N-H⋯N hydrogen bonding motif utilizes an endogenous proton for long-wavelength emission or an exogenous proton for acid-base chemistry, the balance of which is exploited for fluorescence switching in the solid state.
View Article and Find Full Text PDFJ Phys Chem B
June 2024
Department of Chemistry and Chemical Biology, Indian Institute of Technology (Indian School of Mines) Dhanbad, Dhanbad 826004 Jharkhand, India.
5-(-Butyl)-2-hydroxy-1,3-isophthalaldehyde (5-BHI) is a photochromic material susceptible to either excited state proton transfer or excited state intramolecular proton transfer, depending upon the solvent. However, it has also been found to aggregate in the presence of sodium dodecyl sulfate. In this current study, based on the steady-state and time-resolved spectroscopy, supported by crystallography, quantum chemical density functional theory calculation, and molecular dynamics (MD) simulation, we report on the aggregation of this potential single benzene-based emitter (SBBE) in neat solvents as well as solid phase to modulate its photophysics.
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