Influence of nitro group on solvatochromism, nonlinear optical properties of 3-morpholinobenzanthrone: Experimental and theoretical study

Thomas, Anup; Kirilova, Elena; Nagesh, B.V.; Chaitanya, G. Krishna; Philip, Reji; Manohara, S.R.; Sudeeksha, H.C.; Siddlingeshwar, B.

doi:10.1016/j.jphotochem.2022.114434

Cited by 4 publications

(4 citation statements)

References 49 publications

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“…The first representative of benzanthrone derivatives with a nitro group and a substituted amino group (morpholine residue) was previously synthesized and showed interesting optical properties [ 34 ]. Therefore, we continued the study of such substances using a similar synthesis technique to obtain them.…”

Section: Resultsmentioning

confidence: 99%

“…The obtained spectral data are summarized in Table 2 , Table 3 and Table 4 in comparison with the characteristics of the previously studied unnitrated 3-piperidinobenzanthrone ( 6 ) and 3-pyrrolidinobenzanthrone ( 7 ) (see Scheme 2 ). The photophysical properties of morpholine derivatives have been analyzed in a recent study [ 34 ].…”

Section: Resultsmentioning

confidence: 99%

“…The obtained spectral data are summarized in Tables 2-4 in comparison with the characteristics of the previously studied unnitrated 3-piperidinobenzanthrone ( 6) and 3pyrrolidinobenzanthrone (7) (see Scheme 2). The photophysical properties of morpholine derivatives have been analyzed in a recent study [34]. Amines 4 and 5 absorb light at 450-480 nm, while derivative 3 with a pyrrolidine fragment has a longer wavelength absorption band at 525-560 nm and also exhibits a larger bathochromic shift from nonpolar benzene to polar DMSO (33 nm) than derivatives 4 and 5 (18-19 nm).…”

Section: Spectroscopic Propertiesmentioning

confidence: 99%

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Synthesis and Properties of New 3-Heterylamino-Substituted 9-Nitrobenzanthrone Derivatives

Maļeckis,

Cvetinska,

Puckins

et al. 2023

Molecules

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In the present study, new fluorophores based on disubstituted benzanthrone derivatives were designed starting from 9-nitro-3-bromobenzanthrone with nucleophilic substitution of the bromine atom with some secondary cyclic amines. It has been found that this reaction is positively affected by the presence of a nitro group in comparison with 3-bromobenzanthrone. The new compounds exhibit intense absorption and pronounced luminescent properties in various organic solvents. In this regard, their photophysical properties were evaluated with an experimental study of the solvatochromic behavior of the obtained compounds in various solvents. It has recently been found that the addition of an electron-withdrawing nitro group to the benzanthrone core increases its first- and second-order hyperpolarizability. Such dyes can be used in the fabrication of optical limiter devices. Therefore, the developed fluorescent molecules have a potential prospect for extensive application in optoelectronics.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Spectroscopic Propertiesmentioning

confidence: 99%

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Synthesis and Properties of New 3-Heterylamino-Substituted 9-Nitrobenzanthrone Derivatives

Maļeckis,

Cvetinska,

Puckins

et al. 2023

Molecules

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“…The most important among them is the acceleration of intersystem crossing (ISC) with population of triplet states [34], which are non-luminescent in fluid solutions. Another possible quenching mechanism includes charge transfer to the electron withdrawing nitro group, for example, see [32,35]. In the case of the aminoderivative, the hydrogen bonds with water molecules quench the emission, whereas in DMSO and other non-hydrogen bond donor solvents, the COO − group is poorly solvated, and this favors fluorescence [32].…”

Section: Atommentioning

confidence: 99%

3′-Nitro- and 3′-Aminofluoresceins: Appearance of Previously Missing Dyes

Shekhovtsov,

Omelchenko,

Shishkina

et al. 2023

Colorants

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Contrary to the 4′- and 5′-nitro- and aminofluoresceins, the corresponding 3′-derivatives are practically unexplored. In this paper, we describe the synthesis and spectral properties of 3′-nitrofluorescein and 3′-aminofluorescein, as well as their methyl esters. Among other methods, X-ray analysis, 13C NMR spectroscopy, and ESI mass spectrometry made it possible to establish the molecular structure of the target compounds as well as intermediates and by-products. Some unexpected products, though in small amounts, were revealed within the course of study. Whereas the fluorescence of the double-charged R2− ion of 3′-nitrofluorescein in both aqueous and organic solvents is weak, the R2− anion of 3′-aminofluorescein in a non-hydrogen bonding donor solvent, but not in water, exhibits intensive fluorescence, analogous to the case of 4′- and 5′-aminofluoresceins. Interestingly, the λmax values in water of the R2− ions bearing an NO2 group in the 3′- and 6′-positions are 7 to 10 nm higher than those of the 4′- and 5′-nitro derivatives. The difference was also observed in dimethyl sulfoxide. This correlates with the angles between the xanthene and phthalic planes of the dyes. The dye 3′-aminofluorescein could be used as a fluorescent indicator sensitive to hydrogen bonding ability of the solvent. It could also serve as a platform for synthesizing fluorescent molecular probes for biochemical research, analogous to the very popular application of 4′- and 5′-amino derivatives.

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Synthesis and performance of novel n-type EC/AIE energy storage electrode materials containing triphenylamine and quinazolin groups

Wang,

Zheng,

Lin

2024

J Solid State Electrochem

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Influence of nitro group on solvatochromism, nonlinear optical properties of 3-morpholinobenzanthrone: Experimental and theoretical study

Cited by 4 publications

References 49 publications

Synthesis and Properties of New 3-Heterylamino-Substituted 9-Nitrobenzanthrone Derivatives

Synthesis and Properties of New 3-Heterylamino-Substituted 9-Nitrobenzanthrone Derivatives

3′-Nitro- and 3′-Aminofluoresceins: Appearance of Previously Missing Dyes

Synthesis and performance of novel n-type EC/AIE energy storage electrode materials containing triphenylamine and quinazolin groups

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