Group 14 Metallafluorenes for Lipid Structure Detection and Cellular Imaging

Spikes, Helena J.; Jarrett-Noland, Shelby J.; Germann, Stephan; Olivas, Wendy M.; Braddock‐Wilking, Janet; Dupureur, Cynthia M.

doi:10.3390/csac2021-10455

Cited by 3 publications

(4 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In previous work, we demonstrated that this small library of 2,7-disubstituted sila-and germafluorenes interact with surfactant micelles, exhibiting impressive quantum yields in the presence of surfactants (approaching 100% quantum efficiency) and appreciable emission fold enhancements (5-25x) [20]. We also demonstrated that these compounds have specificity for lipid structures in yeast cells, colocalizing with the lipid droplet stain Nile Red [21].…”

Section: Introductionmentioning

confidence: 62%

See 1 more Smart Citation

Push-pull behavior of 2,7-disubstituted sila- and germafluorenes

Jarrett-Noland

McConnell

Braddock‐Wilking

et al. 2022

Preprint

Self Cite

View full text Add to dashboard Cite

Push-pull dyes exhibit intramolecular charge transfer behavior, which due to changes in dipole moment upon excitation, is the origin of their sensitivity to environment. Such compounds are of interest as probes for bioimaging and as biosensors to monitor cellular dynamics and molecular interactions. Desirable biological probes absorb in the visible region, have high extinction coefficients, high quantum yield and excellent photostability. Fluorophores with scaffolding that can be used to tune and optimize solvatochromic behavior are of particular interest. Here we investigate the environmental sensitivity of a small library of highly fluorescent 2,7-disubstituted sila- and germafluorenes. Density functional theory (DFT) calculations show that charge transfer occurs from the alkyne core out to the 2,7-substitutents and 3,6-methoxy substituents, the hallmark of push-pull behavior. They exhibit a HOMO-LUMO energy gap of about 3 eV with desirable dipole moments ranging from 2-3.25 D. These compounds exhibit desirable Stokes shifts in various solvents, with absorption wavelength maxima varying up to 14 nm in polar solvents and emission wavelength maxima up to 36 nm in polar solvents compared to nonpolar solvents. Interestingly, the dependence of Stokes shift on solvent polarizability are consistent with solvatochromic behavior. With the ability to tune push-pull properties via the 2,7-substituent, these disubstituted sila- and germafluorenes have excellent potential as biological probes.

show abstract

Section: Introductionmentioning

confidence: 62%

“…UV-Vis spectroscopy, fluorescence spectroscopy, and density functional theory (DFT) calculations are utilized. When coupled with high extinction coefficients, quantum yield, and photostability [20] [21], this class of compounds show promise as competitive probes for bioimaging and sensing.…”

Section: Introductionmentioning

confidence: 99%

Push-pull behavior of 2,7-disubstituted sila- and germafluorenes

Jarrett-Noland

McConnell

Braddock‐Wilking

et al. 2022

Preprint

Self Cite

View full text Add to dashboard Cite

show abstract

“…In previous work, we demonstrated that this small library of 2,7-disubstituted sila-and germa uorenes interact with surfactant micelles, exhibiting impressive quantum yields in the presence of surfactants (approaching 100% quantum e ciency) and appreciable emission fold enhancements (5-25x) [20]. We also demonstrated that these compounds have speci city for lipid structures in yeast cells, colocalizing with the lipid droplet stain Nile Red [21].…”

Section: Introductionmentioning

confidence: 62%

Push-pull behavior of 2,7-disubstituted sila- and germafluorenes

Jarrett-Noland

McConnell

Braddock‐Wilking

et al. 2022

Preprint

Self Cite

View full text Add to dashboard Cite

Push-pull dyes exhibit intramolecular charge transfer behavior, which due to changes in dipole moment upon excitation, is the origin of their environmental sensitivity. Such compounds are of interest as probes for bioimaging and as biosensors to monitor cellular dynamics and molecular interactions. Desirable biological probes absorb in the visible region, have high extinction coefficients, high quantum yields and excellent photostability. Fluorophores with scaffolding that can be used to tune and optimize solvatochromic behavior are of particular interest. Here we investigate the environmental sensitivity of a small library of highly fluorescent 2,7-disubstituted sila- and germafluorenes. Density functional theory calculations show that charge transfer occurs from the alkyne core out to the 2,7- and 3,6-methoxy substituents, the hallmark of push-pull behavior. They exhibit HOMO-LUMO energy gaps of about 3 eV with dipole moments ranging from 2-3.25 D. These compounds exhibit desirable Stokes shifts in various solvents, and the dependences of Stokes shift on solvent polarizability are consistent with solvatochromic behavior. With the ability to tune push-pull properties via the 2,7-substituent, these disubstituted sila- and germafluorenes have excellent potential as biological probes.

show abstract

“…First, this substituent does influence spectral behavior ( , λ max , and quantum yield), which indicates that these substitutions can be an effective means of tuning these properties [29]. We showed that a few 2,7-disubstituted metallafluorenes can detect detergents and stain cells [63,64].…”

Section: Use Of Dft In Probe Design: 27-disubstituted Metallafluorenesmentioning

confidence: 88%

Use of DFT Calculations as a Tool for Designing New Solvatochromic Probes for Biological Applications

Dupureur

2024

Liquids

View full text Add to dashboard Cite

The intramolecular charge transfer behavior of push–pull dyes is the origin of their sensitivity to environment. Such compounds are of interest as probes for bioimaging and as biosensors to monitor cellular dynamics and molecular interactions. Those that are solvatochromic are of particular interest in studies of lipid dynamics and heterogeneity. The development of new solvatochromic probes has been driven largely by the need to tune desirable properties such as solubility, emission wavelength, or the targeting of a particular cellular structure. DFT calculations are often used to characterize these dyes. However, if a correlation between computed (dipole moment) and experimentally measured solvatochromic behavior can be established, they can also be used as a design tool that is accessible to students. Here, we examine this correlation and include case studies of the effects of probe modifications and conformation on dipole moments within families of solvatochromic probes. Indeed, the ground state dipole moment, an easily computed parameter, is correlated with experimental solvatochromic behavior and can be used in the design of new environment-sensitive probes before committing resources to synthesis.

show abstract

Group 14 Metallafluorenes for Lipid Structure Detection and Cellular Imaging

Cited by 3 publications

References 14 publications

Push-pull behavior of 2,7-disubstituted sila- and germafluorenes

Push-pull behavior of 2,7-disubstituted sila- and germafluorenes

Push-pull behavior of 2,7-disubstituted sila- and germafluorenes

Use of DFT Calculations as a Tool for Designing New Solvatochromic Probes for Biological Applications

Contact Info

Product

Resources

About