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Journal article
Solvatochromic Study of 2‑(N,N‑dimethyl)-3-alkynyl-pyridine Fluorophores
ACS omega, Vol.11(25), pp.38106-38113
06/30/2026
PMID: 42396038
Web of Science ID: WOS:001799513600001
Abstract
A series of pyridine-based fluorophores─2-(N,N-dimethyl)-3-alkynyl-pyridine (NNDAP), 4-[2-[2-(dimethylamino)-3-pyridyl]ethynyl]anisole (NNDAP-OMe), and 4-[2-[2-(dimethylamino)-3-pyridyl]ethynyl]benzonitrile (NNDAP-CN)─were synthesized and their solvent-dependent photophysical properties were systematically investigated. Solvatochromic shifts in absorption and emission spectra were analyzed using the Bilot–Kawski, Lippert–Mataga, Bakhshiev, and Reichardt correlation methods to estimate ground- and first excited-state electric dipole moments. All compounds exhibit increased polarity in the excited state, with NNDAP-CN showing the largest change in dipole moment upon excitation. Solute–solvent interactions were also examined using the Kamlet–Taft and Catalán multiparameter linear solvation energy relationship models, revealing that solvent dipolarity/polarizability interactions influence absorption shifts, while emission shifts are influenced by a combination of solvent dipolarity/polarizability and solvent basicity. All fluorophores readily permeate HeLa cells and exhibit stable blue fluorescence localized primarily in the perinuclear cytoplasmic region, supporting their potential application as environment-sensitive fluorescent probes.
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- Title
- Solvatochromic Study of 2‑(N,N‑dimethyl)-3-alkynyl-pyridine Fluorophores
- Publication Details
- ACS omega, Vol.11(25), pp.38106-38113
- Resource Type
- Journal article
- Publisher
- American Chemical Society
- Number of pages
- 8
- Grant note
- Hal Marcus College of Science and Engineering, University of West Florida: NA
The authors are thankful for the support provided by the University of West Florida (UWF), the UWF Hal Marcus College of Science and Engineering, and the UWF's Office of Research and Sponsored Programs and the Office of Undergraduate Research. Thanks are also due to Quantachrome (an Anton Paar company) for performing the density measurements.
- Copyright
- © 2026 The Authors.
- Identifiers
- WOS:001799513600001; 99381828383106600
- Academic Unit
- Biology; Chemistry; Hal Marcus College of Science and Engineering ; Physics
- Language
- English