Chemiluminescence properties of luminol related quinoxaline analogs: Experimental and DFT based approach to photophysical properties

Deshmukh, Mininath S.; Sekar, Nagaiyan

doi:10.1016/j.dyepig.2015.02.006

Cited by 6 publications

(5 citation statements)

References 30 publications

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“…Initially, dimethyl 1,3-diphenyl-1H-pyrazolo [3,4-b]pyridine-4,5-dicarboxylate 8 and diethyl 1,3-diphenyl-1H-pyrazolo [3,4-b]pyridine-4,5-dicarboxylate 9 were prepared by following our previously reported literature [24] from N,N-diisopropylamidinyl pyrazolylimine and chosen as the model substrate for this investigation on the construction of pyrazolopyridopyridazine diones 6a (Scheme 1). Compounds 8 and 9 were reacted with hydrazine hydrate at reflux in methanol or ethanol solution under the basic condition for 24-36 h [25,26]. However, all the efforts for the predominant formation of 6a were unsuccessful.…”

Section: Resultsmentioning

confidence: 99%

“…The crude desired products 6a-j were recrystallized in acetone/THF (1/4) solution to obtain the pure pyrazolopyridopyridazine diones 6a-j in 11-84% yields. The low solubility of the compounds 6a-j made the 13 C-NMR characterization of quaternary and carbonyl carbons of these substrates unclear [25,26].…”

Section: Standard Procedures For Synthesis Of Pyrazolopyridopyridazine Diones 6a-jmentioning

confidence: 99%

“…Molecules 2020, 25, x 2 of 16 presumptive test agents for latent blood detection [6][7][8][9], high-performance liquid chromatography (HPLC) [10,11], DNA, immunoassay, and cancer screening detection [12,13]. Since now, many newly designed luminol structures have been enthusiastically investigated to increase the chemiluminescence efficiency, intensity, sensitivity, quantum yield, or the recognition ability of the resulting chemiluminogens (Figure 1) [14][15][16][17][18][19].…”

Section: Introductionmentioning

confidence: 99%

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Selective Synthesis and Photoluminescence Study of Pyrazolopyridopyridazine Diones and N-Aminopyrazolopyrrolopyridine Diones

et al. 2020

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The newly designed luminol structures of pyrazolopyridopyridazine diones and N-aminopyrazolopyrrolopyridine diones were synthesized from versatile 1,3-diaryfuropyrazolopyridine-6,8-diones, 1,3-diarylpyrazolopyrrolopyridine-6,8-diones, or 1,3-diaryl-7-methylpyrazolopyrrolopyridine-6,8-diones with hydrazine monohydrate. Photoluminescent and solvatofluorism properties containing UV–Vis absorption, emission spectra, and quantum yield (Φf) study of pyrazolopyridopyridazine diones and N-aminopyrazolopyrrolopyridine diones were also studied. Generally, most of pyrazolopyrrolopyridine-6,8-diones 6 exhibited the significant fluorescence intensity and the substituent effect when compared with N-aminopyrazolopyrrolopyridine diones, particularly for 6c and 6j with a m-chloro group. Additionally, the fluorescence intensity of 6j was significantly promoted due to the suitable conjugation conformation. Based on the quantum yield (Φf) study, the value of compound 6j (0.140) with planar structural skeletal was similar to that of standard luminol (1, 0.175).

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Section: Resultsmentioning

confidence: 99%

Section: Standard Procedures For Synthesis Of Pyrazolopyridopyridazine Diones 6a-jmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Selective Synthesis and Photoluminescence Study of Pyrazolopyridopyridazine Diones and N-Aminopyrazolopyrrolopyridine Diones

et al. 2020

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“…This reveals that the charge transfer interaction may be taking place within the molecule through the π-conjugated bridge. [28][29][30][31] Scheme 3. Probable CL mechanism of 2 like molecule of luminol bridged by azo link has been prepared.…”

Section: Density Functional Theory Studiesmentioning

confidence: 99%

Green Chemiluminescence of Highly Fluorescent Symmetrical Azo-Based Luminol Derivative

Deepa¹,

Reddy²,

Rajendrakumar³

2018

Orient. J. Chem

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A symmetrical azo-based Luminol derivative 2 was synthesized using catalytic dehydrogenative coupling reaction procedure. This symmetrical molecule shows blue fluorescence in polar aprotic solvents (λ max = 450 nm). With an increase in aqueous content 2 was exhibiting aggregation caused fluorescence quenching (ACQ) with a red shift of 30 nm (λ max = 480 nm). Distinct emission features were observed for this molecule with a variation in the pH range. In basic medium, deprotonated form of 2 shows fluorescence quenching followed by enhancement of green chemiluminescence (λ max = 490 nm) with H 2 O 2 /Fe 3+ catalytic system. The fluorescence and chemiluminescent (CL) properties of 2 were compared with its parent luminol 1, The CL emission intensity of 2 was found to be about 16 times higher than that of 1. In addition, HOMO-LUMO energy gap for 2 was also calculated using density functional theory (DFT) studies.

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“…Various representative chemiluminescent compounds such as luminol, [1][2][3][4] indole, [5,6] acridinium ester [7][8][9][10] and lophine derivatives [11,12] were developed and the chemiluminescence (CL) properties of each were studied. However, these representative chemiluminescent compounds require strongly alkaline conditions to obtain strong CL intensity.…”

Section: Introductionmentioning

confidence: 99%

Enhancement effect on the chemiluminescence of acridinium esters under neutral conditions

Nakazono

Nanbu

2017

Luminescence

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Enhancement effect on the chemiluminescence of acridinium ester derivatives under neutral conditions was investigated. Additions of phenols did not enhance the chemiluminescence intensities of acridinium ester derivatives in the presence of horseradish peroxidase and hydrogen peroxide. Additions of cetyltrimethylammonium bromide apparently enhanced the chemiluminescence intensities of phenyl 10-methyl-10λ -acridine-9-carboxylate derivatives with electron-withdrawing groups at the 4-position of the phenyl group. In particular, the chemiluminescence intensity of 4-(trifluoromethyl)phenyl 10-methyl-10λ -acridine-9-carboxylate trifluoromethanesulfonate salt was 5.5 times stronger in the presence of cetyltrimethylammonium bromide than in its absence at pH 7. The chemiluminescence intensity of 3,4-dicyano-phenyl 10-methyl-10λ -acridine-9-carboxylate trifluoromethanesulfonate salt was 46 times stronger in the presence of cetyltrimethylammonium bromide at pH 7 than in its absence at pH 10.

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Chemiluminescence properties of luminol related quinoxaline analogs: Experimental and DFT based approach to photophysical properties

Cited by 6 publications

References 30 publications

Selective Synthesis and Photoluminescence Study of Pyrazolopyridopyridazine Diones and N-Aminopyrazolopyrrolopyridine Diones

Selective Synthesis and Photoluminescence Study of Pyrazolopyridopyridazine Diones and N-Aminopyrazolopyrrolopyridine Diones

Green Chemiluminescence of Highly Fluorescent Symmetrical Azo-Based Luminol Derivative

Enhancement effect on the chemiluminescence of acridinium esters under neutral conditions

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