scholarly journals Rational Design and Synthesis of Large Stokes Shift 2,6-Sulphur-Disubstituted BODIPYs for Cell Imaging

Chemosensors ◽  
2022 ◽  
Vol 10 (1) ◽  
pp. 19
Author(s):  
Abigail E. Reese ◽  
Charles Lochenie ◽  
Ailsa Geddis ◽  
Luana A. Machado ◽  
Marcos C. de Souza ◽  
...  

Five new disubstituted 2,6-thioaryl-BODIPY dyes were synthesized via selective aromatic electrophilic substitution from commercially available thiophenols. The analysis of the photophysical properties via absorption and emission spectroscopy showed unusually large Stokes shifts for BODIPY fluorophores (70–100 nm), which makes them suitable probes for bioimaging. Selected compounds were evaluated for labelling primary immune cells as well as different cancer cell lines using confocal fluorescence microscopy.

2021 ◽  
Vol 9 ◽  
Author(s):  
Roberta Tabone ◽  
Dominik Feser ◽  
Enrico D. Lemma ◽  
Ute Schepers ◽  
Claudia Bizzarri

Novel heteroleptic ZnII bis(dipyrrinato) complexes were prepared as intriguing emitters. With our tailor-made design, we achieved far-red emissive complexes with a photoluminescence quantum yield up to 45% in dimethylsulfoxide and 70% in toluene. This means that heteroleptic ZnII bis(dipyrrinato) complexes retain very intense emission also in polar solvents, in contrast to their homoleptic counterparts, which we prepared for comparing the photophysical properties. It is evident from the absorption and excitation spectra that heteroleptic complexes present the characteristic features of both ligands: the plain dipyrrin (Lp) and the π-extended dipyrrin (Lπ). On the contrary, the emission comes exclusively from the π-extended dipyrrin Lπ, suggesting an interligand nonradiative transition that causes a large pseudo-Stokes shift (up to 4,600 cm−1). The large pseudo-Stokes shifts and the emissive spectral region of these novel heteroleptic ZnII bis(dipyrrinato) complexes are of great interest for bioimaging applications. Thus, their high biocompatibiliy with four different cell lines make them appealing as new fluorophores for cell imaging.


Synlett ◽  
2022 ◽  
Author(s):  
Eva Bednářová ◽  
Logan R. Beck ◽  
Tomislav Rovis ◽  
Samantha L. Goldschmid ◽  
Katherine Xie ◽  
...  

AbstractThe use of low-energy deep-red (DR) and near-infrared (NIR) light to excite chromophores enables catalysis to ensue across barriers such as materials and tissues. Herein, we report the detailed photophysical characterization of a library of OsII polypyridyl photosensitizers that absorb low-energy light. By tuning ligand scaffold and electron density, we access a range of synthetically useful excited state energies and redox potentials.1 Introduction1.1 Scope1.2 Measuring Ground-State Redox Potentials1.3 Measuring Photophysical Properties1.4 Synthesis of Osmium Complexes2 Properties of Osmium Complexes2.1 Redox Potentials of Os(L)2-Type Complexes2.2 Redox Potentials of Os(L)3-Type Complexes2.3 UV/Vis Absorption and Emission Spectroscopy3 Conclusions


Molecules ◽  
2018 ◽  
Vol 23 (12) ◽  
pp. 3051 ◽  
Author(s):  
Jacqueline Gayton ◽  
Shane Autry ◽  
Ryan Fortenberry ◽  
Nathan Hammer ◽  
Jared Delcamp

Near-infrared emissive materials with tunable Stokes shifts and solid-state emissions are needed for several active research areas and applications. To aid in addressing this need, a series of indolizine-cyanine compounds varying only the anions based on size, dipole, and hydrophilicity were prepared. The effect of the non-covalently bound anions on the absorption and emission properties of identical π-system indolizine-cyanine compounds were measured in solution and as thin films. Interestingly, the anion choice has a significant influence on the Stokes shift and molar absorptivities of the dyes in solution. In the solid-state, the anion choice was found to have an effect on the formation of aggregate states with higher energy absorptions than the parent monomer compound. The dyes were found to be emissive in the NIR region, with emissions peaking at near 900 nm for specific solvent and anion selections.


RSC Advances ◽  
2015 ◽  
Vol 5 (87) ◽  
pp. 70958-70967 ◽  
Author(s):  
Ajay Kanungo ◽  
Dipendu Patra ◽  
Sanghamitra Mukherjee ◽  
Tridib Mahata ◽  
Prakas R. Maulik ◽  
...  

Synthesis and live cell imaging of a novel fluorescent scaffold which is emissive in the visible range with large stokes shifts.


2015 ◽  
Vol 56 (21) ◽  
pp. 2749-2753 ◽  
Author(s):  
Yanjun Qiao ◽  
Jingtian Chen ◽  
Xuegang Yi ◽  
Wenfeng Duan ◽  
Baoxiang Gao ◽  
...  

2021 ◽  
Vol 18 ◽  
Author(s):  
Amira K. Hajri ◽  
Marzough A. Albalawi ◽  
Souad A. Moussa ◽  
Faouzi Aloui

Background: Three polycyclic aromatic hydrocarbons derived from benzo[c]phenanthrene have been synthesized through a one-step procedure involving palladium Suzuki coupling and are characterized by 1 H and 13C NMR, MS and HRMS spectroscopies. Methods: UV-vis absorption and fluorescence properties of these π-conjugated compounds have been evaluated in solutions and strong emission in the blue region of the visible spectrum was noted. Results: The optical spectra of these small polycyclic aromatic compounds are unusual because absorption is entirely in the UV region (λmax = 281-285 nm), yet fluorescence occurs at 410-422 nm. Conclusion: This equates to a Stokes shift of 1.32-1.39 eV (10756-11256 cm−1 ) and is among the large Stokes shifts that have been reported for small molecules, making them promising candidates for optoelectronic applications.


2020 ◽  
Author(s):  
Zeyu Liu ◽  
Shugui Hua ◽  
Tian Lu ◽  
Ziqi Tian

Inspired by a previous experimental study on the first-order hyperpolarizabilities of 1,3-thiazolium-5-thiolates mesoionic compounds using Hyper-Rayleigh scattering technique, we theoretically investigated the UV-Vis absorption spectra and every order polarizabilities of these mesoionic molecules. Based on the fact that the photophysical and nonlinear properties observed in the experiment can be perfectly replicated, our theoretical calculations explored the essential characteristics of the optical properties of the mesoionic compounds with different electron-donating groups at the level of electronic structures through various wave function analysis methods. The influence of the electron-donating ability of the donor on the optical properties of the molecules and the contribution of the mesoionic ring moiety to their optical nonlinearity are clarified, which have not been reported by any research so far. This work will help people understand the nature of optical properties of mesoionic-based molecules and provide guidance for the rational design of molecules with excellent photoelectric performance in the future.


2020 ◽  
Vol 85 (16) ◽  
pp. 10552-10560
Author(s):  
Peng Sang ◽  
Yan Shi ◽  
Pirada Higbee ◽  
Minghui Wang ◽  
Sami Abdulkadir ◽  
...  

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