One-Pot Synthesis of Dihydrothiazole-Hydrazone Hybrids and Evaluation of Their Absorption and Emission Properties
- 1Manipal Institute of Technology, Manipal Academy of Higher Education, Manipal, India
Abstract
A simple, one-pot method for the synthesis of seven novel dihydrothiazole-hydrazone compounds is presented, employing a condensation-cyclization protocol, with the products characterized by FTIR, 1H NMR, 13C NMR, and ESI-MS. Thiazoles and hydrazones are distinguished by versatile chelating properties and fluorescent conjugated scaffolds, and their combination can be considered a promising route to obtaining tunable fluorophores. According to the UV-Vis absorption and fluorescence data, all seven compounds demonstrated absorption maxima at 412–420 nm and emitted a yellow-green light at 554–575 nm. The substituent present at the C-4 position of the dihydrothiazole ring governed the emission wavelength and intensity. Electron-donating groups increased emission intensity and shifted the emission to longer wavelengths, whereas electron-withdrawing groups quenched fluorescence, likely via a photoinduced electron transfer (PET) deactivation mechanism. The Stokes shifts (142–155 nm) also followed the same substituent-dependent pattern. Moderate fluorescence quantum yields (1.64–5.54%) were observed for the thiazoles, indicating that the presence of different functional groups influenced the efficiency of excited-state relaxation. The way substitution influences absorption and emission behavior establishes the dihydrothiazole-hydrazone core as a versatile unit that can be tuned to serve as a fluorophore for sensing, biological, and optoelectronic applications.
Graphical Abstract:
Supplementary Information: The online version contains supplementary material available at https://doi.org/10.1007/s10895-026-04955-6.
Related
- Multistep synthesis of novel indole–benzimidazole hydrazone hybrids as xanthine oxidase inhibitors: In-Vitro evaluation, molecular docking, MD simulations and DFT studies
- Novel Thiochroman‐4‐One Derivatives Bearing a Sulfonyl Hydrazone Moiety: Synthesis, Bioactivity, Molecular Simulation, and Drug‐Likeness Evaluation
- Preliminary in vitro evaluation of anti-leukemic and antimalarial activities of pyrrolo[1,2-a]quinoxaline-carboxylic acid hydrazone derivatives.
- Green synthesis of ZnO nanoparticles using pomegranate husk extract: comparative evaluation of antioxidant, enzyme inhibition, and cytotoxic properties
- From Mono- to Tetranuclear: A Silsesquioxane-Anchored Cu(I) Chromophore Array with Additive Absorption and Preserved Excited-State Properties
BibTeX
@article{d2026onepot,
title = {{One-Pot Synthesis of Dihydrothiazole-Hydrazone Hybrids and Evaluation of Their Absorption and Emission Properties}},
author = {Charan D. C. and Yogeesh M. and Nitinkumar S. Shetty},
journal = {Journal of Fluorescence},
year = {2026},
month = sep,
doi = {10.1007/s10895-026-04955-6},
url = {https://doi.org/10.1007/s10895-026-04955-6},
note = {CC BY 4.0},
}
RIS
TY - JOUR
TI - One-Pot Synthesis of Dihydrothiazole-Hydrazone Hybrids and Evaluation of Their Absorption and Emission Properties
AU - Charan D. C.
AU - Yogeesh M.
AU - Nitinkumar S. Shetty
PY - 2026
DA - 2026/09/29
JO - Journal of Fluorescence
DO - 10.1007/s10895-026-04955-6
UR - https://doi.org/10.1007/s10895-026-04955-6
AB - A simple, one-pot method for the synthesis of seven novel dihydrothiazole-hydrazone compounds is presented, employing a condensation-cyclization protocol, with the products characterized by FTIR, 1H NMR, 13C NMR, and ESI-MS. Thiazoles and hydrazones are distinguished by versatile chelating properties and fluorescent conjugated scaffolds, and their combination can be considered a promising route to obtaining tunable fluorophores. According to the UV-Vis absorption and fluorescence data, all seven compounds demonstrated absorption maxima at 412–420 nm and emitted a yellow-green light at 554–575 nm. The substituent present at the C-4 position of the dihydrothiazole ring governed the emission wavelength and intensity. Electron-donating groups increased emission intensity and shifted the emission to longer wavelengths, whereas electron-withdrawing groups quenched fluorescence, likely via a photoinduced electron transfer (PET) deactivation mechanism. The Stokes shifts (142–155 nm) also followed the same substituent-dependent pattern. Moderate fluorescence quantum yields (1.64–5.54%) were observed for the thiazoles, indicating that the presence of different functional groups influenced the efficiency of excited-state relaxation. The way substitution influences absorption and emission behavior establishes the dihydrothiazole-hydrazone core as a versatile unit that can be tuned to serve as a fluorophore for sensing, biological, and optoelectronic applications. Graphical Abstract: Supplementary Information: The online version contains supplementary material available at https://doi.org/10.1007/s10895-026-04955-6.
SN - 1053-0509
SN - 1573-4994
ER -