New substituted imidazo[1,5-a]pyridine and imidazo[5,1-a]isoquinoline derivatives and their application in fluorescence cell imaging

Volpi, Giorgio; Lace, Beatrice; Garino, Claudio; Priola, Emanuele; Artuso, Emma; Vioglio, Paolo Cerreia; Barolo, Claudia; Fin, Andréa; Genre, Andrea; Prandi, Cristina

doi:10.1016/j.dyepig.2018.04.037

Cited by 37 publications

(36 citation statements)

References 51 publications

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“…Imidazo [1,5-a]pyridines are a promising family of fluorophores that can be easily functionalized to tune their photophysical properties, characterized by a high photoluminescent quantum yield (up to 50%) and a large Stokes shift (up to 150 nm) [1][2][3][4]. The synthetic feasibility via a one-pot cyclocondensation reaction, without the use of any metal catalyst or highly sensitive Lewis acid, has been previously demonstrated [5,6].…”

Section: Introductionmentioning

confidence: 99%

Microwave-Assisted Synthesis, Optical and Theoretical Characterization of Novel 2-(imidazo[1,5-a]pyridine-1-yl)pyridinium Salts

et al. 2021

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In the last few years, imidazo[1,5-a]pyridine scaffolds and derivatives have attracted growing attention due to their unique chemical structure and optical behaviors. In this work, a series of pyridylimidazo[1,5-a]pyridine derivatives and their corresponding pyridinium salts were synthesized and their optical properties investigated to evaluate the effect of the quaternization on the optical features both in solution and polymeric matrix. A critical analysis based on the spectroscopic data, chemical structures along with density functional theory calculation is reported to address the best strategies to prevent aggregation and optimize the photophysical properties. The obtained results describe the relationship between chemical structure and optical behaviors, highlighting the role of pendant pyridine. Finally, the presence of a positive charge is fundamental to avoid any possible aggregation process in polymeric films.

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Section: Introductionmentioning

confidence: 99%

Microwave-Assisted Synthesis, Optical and Theoretical Characterization of Novel 2-(imidazo[1,5-a]pyridine-1-yl)pyridinium Salts

et al. 2021

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“…Using 1‐(pyridin‐2‐yl)‐3‐(quinolin‐2‐yl)imidazo[1,5‐ a ]quinoline in a layer architecture with typical contact materials, blue OLEDs were prepared recently . The substitution with different functional groups up to now has mainly been studied on the IP core . The increase in the size of the π‐system at the chromophore unit can affect quantum yield and absorbance wavelength, determined by the gap between frontier orbitals .…”

Section: Introductionmentioning

confidence: 99%

Optimization of the Substitution Pattern of 1,3‐Disubstituted Imidazo[1,5‐a]Pyridines and ‐Quinolines for Electro‐Optical Applications

Albrecht

Rössiger

Herr

et al. 2020

Physica Status Solidi (b)

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A series of recently synthesized 1,3‐disubstituted imidazo[1,5‐a]pyridines (IPs) and ‐quinolines (IQs) targeting at increased efficiency of luminescence is investigated. The properties of molecules in solution as well as their change in the solid state are reported and assessed regarding possible application in organic electronics. The influence of increased ring size by substitution, e.g., exchanging phenyl to naphthalenyl, as well as pyridyl to quinolinyl moieties, and by means of a larger IQ fluorophore is discussed. A higher oscillator strength and quantum yield can be achieved. Frontier orbital energies are estimated based on cyclic voltammetry and density functional theory (DFT) calculations. Single crystals of molecules are grown. A red‐shift in the photoluminescence spectra found for crystals of IQs compared with those in solution is proposed to be caused by intermolecular coupling based on the parallel stacking of the enlarged fluorophore units. Thin films deposited by physical vapor deposition exhibit similar effects, showing promise as active layers in organic light‐emitting diodes (OLEDs). An amorphous morphology is inferred for these films from both spectral broadening in photoluminescence and atomic force microscopy. An OLED test structure is prepared, using the most efficient IQ lumophore and demonstrating the feasibility of obtaining electroluminescence from such thin films.

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“…Most synthetic approaches rely on various cyclocondensations of nucleophilic (2-aminomethyl)pyridine precursors, introducing a new five-membered ring. Typically, carboxylic acids [16][17][18][19][20], acyl anhydrides [21][22][23], acyl chlorides [24][25][26][27], esters [28], thioamides [29][30][31], dithionates [32,33], or thiocarbamates [34] are employed as electrophilic components, but oxidative cyclocondensations with aldehydes have also been showcased [35][36][37]. However, given the importance of these targets, new preparative methods are still in high demand.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of imidazo[1,5-a]pyridines via cyclocondensation of 2-(aminomethyl)pyridines with electrophilically activated nitroalkanes

Аксенов

Arutiunov

Maliuga

et al. 2020

Beilstein J. Org. Chem.

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New substituted imidazo[1,5-a]pyridine and imidazo[5,1-a]isoquinoline derivatives and their application in fluorescence cell imaging

Cited by 37 publications

References 51 publications

Microwave-Assisted Synthesis, Optical and Theoretical Characterization of Novel 2-(imidazo[1,5-a]pyridine-1-yl)pyridinium Salts

Microwave-Assisted Synthesis, Optical and Theoretical Characterization of Novel 2-(imidazo[1,5-a]pyridine-1-yl)pyridinium Salts

Optimization of the Substitution Pattern of 1,3‐Disubstituted Imidazo[1,5‐a]Pyridines and ‐Quinolines for Electro‐Optical Applications

Synthesis of imidazo[1,5-a]pyridines via cyclocondensation of 2-(aminomethyl)pyridines with electrophilically activated nitroalkanes

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