One pot synthesis of low cost emitters with large Stokes' shift

Volpi, Giorgio; Magnano, Guido; Benesperi, Iacopo; Saccone, Davide; Priola, Emanuele; Gianotti, Valentina; Milanesio, Marco; Conterosito, Eleonora; Barolo, Claudia; Viscardi, Guido

doi:10.1016/j.dyepig.2016.09.056

Cited by 55 publications

(47 citation statements)

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“…Therefore, to clarify the preferential reaction site, 1 H and 13 C NMR spectra were assigned with the help of the homonuclear correlation spectroscopy (COSY) method-Figure 2 and Figures S1-S4. Taking into account 1 H NMR, it is also noteworthy to mention that, in all the cases, the ratio between the aliphatic and aromatic regions inferred a reaction stoichiometry equal to 1:1 with respect to the pyridylimidazo [1,5-a]pyridine core and alkyl chain-Figures S2, S12 and S16. This first evidence also excludes a possible multi-quaternization step.…”

Section: Note About the Synthesismentioning

confidence: 91%

“…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%

“…The following are available online at https://www.mdpi.com/article/10 .3390/chemistry3030050/s1, FigureS1: the 1 H NMR spectrum of Acetone-d 6 solution of 1, FigureS2: the1 H NMR spectrum of Acetone-d 6 solution of 1q, FigureS3: the 2D 1 H-COSY NMR spectrum of Acetone-d 6 solution of 1, FigureS4: the 2D 1 H-COSY NMR spectrum of Acetone-d 6 solution of 1q, FigureS5: the13 C NMR spectrum of Acetone-d 6 solution of 1, Figure S6: the 13 C NMR spectrum of Acetone-d 6 solution of 1q, Figure S7: the 13 C DEPT-135 NMR spectrum of Acetone-d 6 solution of 1, Figure S8: the 13 C DEPT-135 NMR spectrum of Acetone-d 6 solution of 1q, Figure S9: the 1 H NMR spectrum of Chloroform-d 3 solution of 2, Figure S10: the 2D 1 H COSY-NMR spectrum of Chloroform-d 3 solution of 2, Figure S11: the 13 C NMR spectrum of Chloroform-d 3 solution of 2, Figure S12: the 1 H NMR spectrum of Methanol-d 4 solution of 2q, Figure S13: the 1 H NMR spectrum of Chloroform-d 3 solution of 3, Figure S14: the 2D 1 H COSY-NMR spectrum of Chloroform-d 3 solution of 3, Figure S15: the 13 C NMR spectrum of Chloroform-d 3 solution of 3, Figure S16: the 1 H NMR spectrum of Methanol-d 4 solution of 3q, Figure S17: experimental and calculated absorption spectra of 2, Figure S18: experimental and calculated absorption spectra of 2q, Figure S19: experimental and calculated absorption spectra of 3, Figure S20: experimental and calculated absorption spectra of 3q, Figure S21: molecular orbital plots (LUMO and HOMO) of the reported compounds, Figure S22: absorption and emission spectra of 1 recorded in DCM solution (concentration 10 −5 M) and in thin film, Figure S23: emission spectra of 1 recorded in different conditions: DCM solution, thin film, and blended in PMMA and in PS, Figure S24: absorption and emission spectra of 1q recorded in DCM solution (concentration 10 −5 M), in thin film and blended in PS matrix, Figure S25: absorption and emission spectra of 2 recorded in DCM solution (concentration 10 −5 M), in thin film and blended in PS matrix, Figure S26: absorption and emission spectra of 3 recorded in DCM solution (concentration 10 −5 M), in thin film and blended in PS matrix. Author Contributions: Conceptualization, G.V.…”

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confidence: 99%

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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: Note About the Synthesismentioning

confidence: 91%

Section: Introductionmentioning

confidence: 99%

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confidence: 99%

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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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“…311+G (d,p) model. Furthermore, superior absorption characteristics in a particular spectral region and intensive emission properties with large Stokes shifts are essential requirements for all organic emitters (Volpi et al, 2017). The Stokes shift is the difference in energy between emission and absorption maxima, and when this shift is small, parts of the emission and absorption spectra can overlap.…”

Section: Figure 10mentioning

confidence: 99%

Structural and optical profile of a multifunctionalized 2-pyridone derivative in a crystal engineering perspective

Joy

Anabha²,

Gopi

et al. 2018

Acta Crystallogr C

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The supramolecular structural features of organic molecules are very important with regard to their widespread properties in both solids and solutions. Herein, we describe the synthesis of a novel multifunctional 2-pyridone derivative, namely 6-(4-chlorophenyl)-5-formyl-4-methylsulfanyl-2-oxo-1,2-dihydropyridine-3-carbonitrile, CHClNOS, denoted P1, and its structural features were established through X-ray crystallography. A Hirshfeld surface analysis followed by a two-dimensional fingerprint plot analysis was carried out. A frontier molecular orbital investigation and natural bond orbital (NBO) calculations explored the charge-transfer interactions associated with the molecular system. The optical properties of the 2-pyridone derivative were elucidated through UV-Vis absorption and emission spectroscopy, indicating a strong blue emissive nature with a colour purity of 82.5%, a short-lived lifetime and a large Stokes shift. Time-dependent density functional theory (TD-DFT) was used to gain some insight into the absorption behaviour and emissive characteristics of P1.

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“…The difference between the “excitation” and the “fluorescence” peak is known as “Stokes-shift”. Large Stokes-shifts improve fluorescence signal due to a decreased overlap between the absorbance and the emission bands [ 3 ]. Fluorescence and absorption spectroscopy can be considered complementary techniques and provide response in the visible spectral region and are employed as analytical chemistry tools to quantify the amount of a particular analyte in the sample [ 4 ].The first stage of an optical sensor transduction involves a chemical interaction between the analyte and a transductor to produce an optically detectable signal.…”

Section: Introductionmentioning

confidence: 99%

Visual pH Sensors: From a Chemical Perspective to New Bioengineered Materials

Costanzo

Panunzi

2021

Molecules

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Many human activities and cellular functions depend upon precise pH values, and pH monitoring is considered a fundamental task. Colorimetric and fluorescence sensors for pH measurements are chemical and biochemical tools able to sense protons and produce a visible signal. These pH sensors are gaining widespread attention as non-destructive tools, visible to the human eye, that are capable of a real-time and in-situ response. Optical “visual” sensors are expanding researchers’ interests in many chemical contexts and are routinely used for biological, environmental, and medical applications. In this review we provide an overview of trending colorimetric, fluorescent, or dual-mode responsive visual pH sensors. These sensors include molecular synthetic organic sensors, metal organic frameworks (MOF), engineered sensing nanomaterials, and bioengineered sensors. We review different typological chemical entities of visual pH sensors, three-dimensional structures, and signaling mechanisms for pH sensing and applications; developed in the past five years. The progression of this review from simple organic molecules to biological macromolecules seeks to benefit beginners and scientists embarking on a project of pH sensing development, who needs background information and a quick update on advances in the field. Lessons learned from these tools will aid pH determination projects and provide new ways of thinking for cell bioimaging or other cutting-edge in vivo applications.

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One pot synthesis of low cost emitters with large Stokes' shift

Cited by 55 publications

References 52 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

Structural and optical profile of a multifunctionalized 2-pyridone derivative in a crystal engineering perspective

Visual pH Sensors: From a Chemical Perspective to New Bioengineered Materials

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