Synthesis, optical and electrochemical properties of new cyanopyridine derivatives

Mruthunjayappa, Manohara Halanur; Devaiah, C. Trupthi; Hemavathi, B.; Ahipa, T.N.

doi:10.1016/j.jlumin.2018.10.070

Cited by 17 publications

(8 citation statements)

References 23 publications

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“…In the literature, few polycyclic scaffolds cored with electron-donating and withdrawing functionalities have been frequently used for the solvatochromic studies. [51][52][53] Based on the spectral behavior of the synthesized terphenyls in different solvents, it was observed that the compound 7 c exhibits slight red shift in DMSO, DMF and chloroform while slight blue shift in acetonitrile, cyclohexane and 1,4-dioxane (Figure 2a, Supporting Information, Table 2). Additionally, the compound 9 a (Figure 2b, Supporting Information, Table 2) and 11 a showed slight red shift in DMSO, DMF and cyclohexane while the blue shift was observed in acetonitrile and 1,4dioxane ( Figure 2c, Supporting Information, Table 2).…”

Section: Photo-physical Studiesmentioning

confidence: 99%

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Metal‐Free Synthesis of Thermally Stable Fluorescent p‐Terphenyls by Ring Transformation of 2H‐Pyran‐2‐ones

Chandrasekar

Singh

2020

ChemistrySelect

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A metal-free approach for the synthesis of p-terphenyls 7 a-i and cyclic p-terphenyls 9 ad and 11 ad is described via carbanion induced ring transformation reaction of 6-biphenyl-2H-pyran-2-ones 5 with malononitrile 6, cyclohexanone 8 and 1,4-cyclohexanedione monoethylene ketal 10 respectively. Additionally, the base-mediated ring transformation reactions were working smoothly under mild reaction conditions and ring transformation products 7, 9 and 11 were isolated in good to excellent yields. The synthetic approach provides the flexibility of introducing of both electron-withdrawing and-donating functionalities in p-terphenyl architecture. Moreover, the photo physical properties of compounds 7, 9 and 11 were analyzed using UV-visible and Fluorescence Spectroscopy. p-Terphenyls 7 c showed cyan fluorescence in chloroform (λ max (em): 508 nm) and acetonitrile (λ max (em): 420 nm) while cyclic p-terphenyl 9 a showed blue fluorescence in chloroform and 1,4-dioxane (λ max (em): 470 nm). Similarly, compound 11 a showed blue fluorescence in chloroform (λ max (em): 468 nm) and 1,4-dioxane (λ max (em): 473 nm). Additionally, the thermal stability of synthesized cyclic p-terphenyls 11 a, 11 c and 11 d were also studied using TG and DTA techniques.

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Section: Photo-physical Studiesmentioning

confidence: 99%

“…The additional peak is probably corresponds to n‐π* transition which arises due to the presence of tertiary amino group in the products. In the literature, few polycyclic scaffolds cored with electron‐donating and withdrawing functionalities have been frequently used for the solvatochromic studies …”

Section: Photo‐physical Studiesmentioning

confidence: 99%

Metal‐Free Synthesis of Thermally Stable Fluorescent p‐Terphenyls by Ring Transformation of 2H‐Pyran‐2‐ones

Chandrasekar

Singh

2020

ChemistrySelect

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“…The observed data also corroborates an assumption about the essential role of the cyano group in the pyridine ring causing the high uorescence of the pyridine derivatives and allows it to act as an excellent uorescent core with good electron-transporting properties. [46][47][48][49][50][51][52] It can be easily observed from the study that our nicotinonitrile-based uorescent type molecules containing pyrene and/or uorene moieties have been proven to be promising uorophores for application as chemo-and biosensors. Moreover, this type of structure with a highly electron decient system could be of interest to many researchers working on the development of n-type organic semiconductors and for the design of new liquid crystal materials.…”

Section: Substituent Effect On Absorption and Emission Spectra Of Thementioning

confidence: 99%

Exploiting a multicomponent domino reaction strategy for the tailoring of versatile environmentally sensitive fluorophore-based nicotinonitriles incorporating pyrene and fluorene moieties

2019

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“…Attributes like absorption and emission characteristics play pivotal roles in applications such as sensors, light emitting diodes, and photovoltaic devices. Simultaneously, the optical properties of pyridine-derived compounds have gained prominence in optoelectronics due to their intriguing photophysical characteristics, which encompass their response to light, including absorption and emission behavior. ,− These compounds have found wide-ranging applications in various fields, including their pivotal role in the development of light-emitting devices, their utility as nonlinear optical materials for advanced technologies, and their multifaceted contributions in diverse areas. , Among these substituted pyridines, halogen-substituted phenylpyridines are known to have fluorescence properties, − which make them remarkable candidates for applications in fluorescent probes and sensors, as well as in the field of molecular imaging. These substituted pyridines are sensitive to their structural modifications.…”

Section: Introductionmentioning

confidence: 99%

From Molecules to Devices: Insights into Electronic and Optical Properties of Pyridine-Derived Compounds Using Density Functional Theory Calculations

Mahmood,

Akram,

Chen

et al. 2024

J. Phys. Chem. A

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In this study, we delve into the electronic structure, spectroscopic, and optical properties of five benzo derivatives of pyridine, namely, 5-(4-chlorophenyl)-2fluoropyridine (1), 2-fluoro-5-(4-fluorophenyl)pyridine (2), 4-(2-fluoropyridin-5-yl)phenol (3), 5-(2,3-dichlorophenyl)-2-fluoropyridine (4), and 5-(5-bromo-2-methoxyphenyl)-2-fluoropyridine (5). Utilizing quantum chemical density functional theory calculations at the B3LYP and Perdew−Burke−Ernzerhof levels of theory combined with the 6-311G(d,p) and 6-311++G(d,p) basis sets, we investigated the electronic and optical characteristics of these compounds. Band structure calculations were conducted for their crystalline structures, revealing a direct band gap varying from 3.018 to 3.558 eV, with the valence band maximum and conduction band minimum located at the G point in the Brillouin zone. The optical properties were analyzed, including the dielectric functions, reflectivity, and refractive index. Notably, reflectivity was found to be minimal in the photon energy range of 0.0−3.0 eV, and the static refractive index, n(0), ranged from 1.55 to 1.70. The research also involved assessing the reactivity of the compounds through calculation of the frontier orbital energy gaps (ΔE), indicating a significant charge transfer and high reactivity. Additionally, we performed frequency analysis to unveil the Fouriertransform infrared spectra of compounds 1−5 at room temperature. Molecular electrostatic potential surfaces of the optimized structures were employed to map the electrophilic and nucleophilic regions of the compounds. This investigation provides a comprehensive understanding of the electronic and optical properties of these pyridine derivatives, shedding light on their potential applications in optoelectronics.

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Synthesis, optical and electrochemical properties of new cyanopyridine derivatives

Cited by 17 publications

References 23 publications

Metal‐Free Synthesis of Thermally Stable Fluorescent p‐Terphenyls by Ring Transformation of 2H‐Pyran‐2‐ones

Metal‐Free Synthesis of Thermally Stable Fluorescent p‐Terphenyls by Ring Transformation of 2H‐Pyran‐2‐ones

Exploiting a multicomponent domino reaction strategy for the tailoring of versatile environmentally sensitive fluorophore-based nicotinonitriles incorporating pyrene and fluorene moieties

From Molecules to Devices: Insights into Electronic and Optical Properties of Pyridine-Derived Compounds Using Density Functional Theory Calculations

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