Highly conjugated D-π-A-π-D form of novel benzo[b]thiophene substituted 1,3,4‑oxadiazole derivatives; Thermal, optical properties, solvatochromism and DFT studies

Najare, Mahesh S.; Patil, Mallikarjun K.; Mantur, Shivaraj; Nadaf, AfraQuasar A.; Inamdar, Sanjeev R.; Khazi, Imtiyaz Ahmed M.

doi:10.1016/j.molliq.2018.09.094

Cited by 19 publications

(4 citation statements)

References 39 publications

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“…Chemistry N-9 substituted 6-morpholino-9H-purine derivatives are synthesized using the standard protocol as outlined in Scheme 1. [38][39][40] The present work involves the nucleophilic substitution of the commercially available 6-chloro purine and subsequent further reactions to obtain the target compounds PP (1-6) and PO (1-6) which were purified by column chromatography. Spectroscopic data of the synthesized compounds confirmed their structures.…”

Section: Resultsmentioning

confidence: 99%

Novel 6‐Morpholino‐9H‐purine Derivatives: Synthesis, Pharmacological and In Silico Evaluation

et al. 2020

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A series of novel N‐9 substituted 6‐morpholino‐9H‐purine derivatives (PP 1–6; PO 1–6) were designed and synthesized via a multi‐step synthetic pathway. Spectroscopic techniques confirmed their chemical structures. The synthesized compounds were screened for in vitro antimicrobial, antioxidant and anti‐inflammatory activities. PP‐3, PP‐5, PP‐6, PO‐2 and PO‐5 have exhibited good activity against all the bacterial strains with MIC 4–8 μg/mL whereas PO‐5 and PO‐6 exhibited strong inhibition of fungal strains (MIC: 2–4 μg/mL). PP‐5 has strongly inhibited C. albicans with MIC 2 μg/mL which is similar to that of Fluconazole standard. The in silico studies performed on C. albicans indicated that their mode of action is by the inhibition of dihydrofolate reductase enzyme. The anti‐inflammatory and antioxidant assays have shown that the halogen substituted derivatives have good anti‐inflammatory properties while the non halogen substituted derivatives exhibited good antioxidant profile.

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Section: Resultsmentioning

confidence: 99%

Novel 6‐Morpholino‐9H‐purine Derivatives: Synthesis, Pharmacological and In Silico Evaluation

et al. 2020

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“…The results are summarized in Table 2 and displayed in Figures 3 and 4. The small change in spectral shifts, both in excitation and emission maxima, is observed in solvents from methanol to toluene for the probes PTZ-6(a-e) which is caused by the change in the polarity of the solvents along with the specific solvent-solute interaction between -OH of substituted aldehydes and imine of Schiff base with solvents [62,63]. The synthesized molecules PTZ-6(a-e) have shown both bathochromic shifts in polar/weakly polar protic solvents, which implies that the probes are stabilized by solvents in the ground state (S0), and hypsochromic shifts in polar aprotic solvents, which confirm that the dye is stabilized in the S0 or S1 state depending on the solvent interacted with the solute molecules [64].…”

Section: Solvatochromismmentioning

confidence: 99%

Orange to red emissive aldehyde substituted donor-π-acceptor phenothiazine derivatives: Optoelectronic, DFT and thermal studies

et al. 2023

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A new class of probes was synthesized using a simple and efficient synthetic protocol. These compounds (PTZ-6(a-e)) have the phenothiazine (PTZ) moiety as the electron donor (D) and substituted aldehydes along with the acrylonitrile group, which acts as the electron acceptor (A), thus making D-π-A push-pull system. The structures of the newly synthesized series of small organic target molecules PTZ-6(a-e) were investigated and confirmed by spectros-copic techniques. The optical/solvatochromic properties were studied in detail by UV-vis absorption and fluorescence spectroscopy, because the molecules have shown good solubility in organic solvents. The density functional theory (DFT) model with the CAM-B3LYP function is utilized to study the photophysical properties of the probes, as these probes exhibited orange-to-red emission. Optical band gap values ranged from 2.32 to 2.50 eV, and these probes exhibited good thermal stability with a melting temperature of 136 to 198 °C and a T5d temperature range from 335 to 354 °C. The cyclic voltammetry study confirms that the Eoxonset values of the target compounds are 0.80 eV. The quantum yields (Φ) of the probes are measured experimentally in ethanol and the Stokes shifts are observed to be in the range of 4846-9430 cm-1. The results displayed that novel (D-A-D) chromophores could play an important role in organic optoelectronics.

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“…A detailed study dedicated to the biological importance of 1,3,4-oxadiazoles and their application in medicine and agriculture was published recently by Luczynski and Kudelko [26]. The electron-deficient oxadiazole ring, in combination with other aromatic groups, is responsible for the unique electronic properties of such compounds, which are responsible for their applications in material engineering [27][28][29][30][31] and optoelectronics [32][33][34][35][36][37].…”

Section: Synthesis Of 134-oxadiazole Precursorsmentioning

confidence: 99%

Arylation Reactions in the Synthesis of Biologically Important 2,5-Diaryl-1,3,4-Oxadiazoles

Olesiejuk

Kudelko

2022

Applied Sciences

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Apart from carbon atoms, some cyclic molecules contain other elements and play an extraordinary role in human life. Among these systems, 1,3,4-oxadiazole derivatives deserve special attention due to their biological properties such as antibacterial, antifungal, antitumor, and anti-inflammatory properties. They are commonly used in pharmacology, as well as in fungicidal, herbicidal, and insecticidal agricultural applications. The 1,3,4-oxadiazole fragment is connected directly to other aromatic systems and can be found in the structure of some commercially available drugs, or in potential drug candidates in the final pharmacological testing phase. Therefore, scientists are looking for new hybrid materials based on 1,3,4-oxadiazoles and other biologically active molecules. The most popular methods for constructing new carbon–carbon bonds between two aromatic species include direct arylation, condensation, and cross-coupling reactions. This review article, comprising the literature from 2009 to 2022, discusses a number of arylation reactions in the synthesis of 2,5-diaryl-1,3,4-oxadiazole derivatives.

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Highly conjugated D-π-A-π-D form of novel benzo[b]thiophene substituted 1,3,4‑oxadiazole derivatives; Thermal, optical properties, solvatochromism and DFT studies

Cited by 19 publications

References 39 publications

Novel 6‐Morpholino‐9H‐purine Derivatives: Synthesis, Pharmacological and In Silico Evaluation

Novel 6‐Morpholino‐9H‐purine Derivatives: Synthesis, Pharmacological and In Silico Evaluation

Orange to red emissive aldehyde substituted donor-π-acceptor phenothiazine derivatives: Optoelectronic, DFT and thermal studies

Arylation Reactions in the Synthesis of Biologically Important 2,5-Diaryl-1,3,4-Oxadiazoles

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