Theoretical Study on the Atom-Substituted Quinazoline Derivatives with Faint Emission as Potential Sunscreens

Zhang, Yajie; Ma, Min; Shang, Changjiao; Cao, Yunjian; Sun, Chaofan

doi:10.1021/acsomega.2c00316

Cited by 8 publications

(6 citation statements)

References 61 publications

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“…The hydrogel, ChCrQ, shows stimulating photophysical properties for their significant keto–enol tautomerization involved in CrQ moieties. , This process, known as excited state intramolecular proton transfer (ESIPT), can be influenced by the hydrogel network’s chemical and physical environment due to functional group variations. In water, ChCrQ shows distinct absorption bands.…”

Section: Resultsmentioning

confidence: 99%

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An Integrated Polysaccharide Hydrogel with Versatile Fluorescence Responses through Noncovalent Reformation of Gel Aggregation and for Bioimaging

Ghorai,

Dasgupta,

Mukherjee

et al. 2024

ACS Appl. Bio Mater.

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Functionalized hydrogels, with their unique and adaptable structures, have attracted significant attention in materials and biomaterials research. Fluorescent hydrogels are particularly noteworthy for their sensing capabilities and ability to mimic cellular matrices, facilitating cell infiltration and tracking of drug delivery. Structural elucidation of hydrogels is crucial for understanding their responses to stimuli such as the pH, temperature, and solvents. This study developed a fluorescent hydrogel by functionalizing chitosan with p-cresol-based quinazolinone aldehyde. Confocal microscopy revealed the hydrogel's intriguing fluorogenic properties. The hydrogel exhibited enhanced fluorescence and a tunable network morphology, influenced by the THF−water ratio. The study investigated the control of gel network reformation in different media and analyzed the fluorescence responses and structural changes of the sugar backbone and fluorophore. Proper selection of mixed solvents is essential for optimizing the hydrogel as a fluorescence probe for bioimaging. This hydrogel demonstrated greater swelling properties, making it highly suitable for drug delivery applications.

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Section: Resultsmentioning

confidence: 99%

“…Conversely, the surrounding oxygen atoms are yellow, reflecting a negative potential due to the presence of lone pairs. 1,39 Figure 7c depicts the various intermolecular interactions among ChCrQ molecules. These interactions 52 include the steric effect (red), van der Waals interactions (green), and H-bonding (blue).…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

An Integrated Polysaccharide Hydrogel with Versatile Fluorescence Responses through Noncovalent Reformation of Gel Aggregation and for Bioimaging

Ghorai,

Dasgupta,

Mukherjee

et al. 2024

ACS Appl. Bio Mater.

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“…The authors have cited additional references within the Supporting Information. [53][54][55][56][57][58][59][60][61][62][63][64][65][66][67][68][69][70]…”

Section: Supporting Informationmentioning

confidence: 99%

Photoisomerization of “Partially Embedded Dihydropyridazine” with a Helical Structure

Usui,

Amano,

Murayama

et al. 2023

Chemistry A European J

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Herein, we report the synthesis of two “partiallyembedded fused‐dihydropyridazine N‐aryl aza[5]helicene derivatives” (PDH) and the demonstration of their intrinsic photo‐triggered multi‐functional properties based on a Kekulé biradical structure. Introducing bulky electron‐withdrawing trifluoromethyl or pentafluoroethyl groups into the aza[5]helicene framework (PDH‐CF3 and ‐C2F5) gives PDH axial chirality based on the helicity of the P and M forms, even at room temperature. Upon photo‐irradiation of PDH‐CF3 in a frozen solution, an ESR signal from the triplet biradical with zero‐field splitting values, generated by N–N bond dissociation, was observed. However, when the irradiation was turned off, the ESR signal became silent, indicating the existence of two equilibriums, between the biradical and quinoidal forms based on the Kekulé structure, and between N–N bond cleavage and recombination. The observed photo‐ and thermally induced behaviors indicate that T‐type photochromic molecules are involved in the photoisomerization mechanism involving the two equilibriums. Inspired by the photoisomerization, chirality control of PDH by photoracemization was achieved. Multiple functionalities, such as T‐type photochromism, photo‐excitation‐mediated triplet biradical formation, and photoracemization, which are attributed to the “partiallyembedded dihydropyridazine” structure, are demonstrated.

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“…Song et al [39] reported that the ESIPT process was easy to occur when the PA in its structure has heavier sulfur atom. Zhang et al [40] designed two new ESIPT compounds on the basis of 2‐(2‐hydroxy‐3‐ethoxyphenyl)‐3 H ‐quinazolin‐4‐one (HQ) by S and Se atoms substitution. They found that the S‐substituted and Se‐substituted compounds can absorb UV light strongly.…”

Section: Introductionmentioning

confidence: 99%

Regulating excited‐state intramolecular proton transfer behavior and fluorescent property of 3‐thiolflavone by electron‐donating ability: A time‐dependent density functional theory study

Zhang

Fang

2023

J Chinese Chemical Soc

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BackgroundSince the excited‐state intramolecular proton transfer (ESIPT) process involving sulfur is extremely fast, its mechanism is still unclear, and its derivatives are rarely studied, we have performed a theoretical study the ESIPT process of 3‐thiolflavone (3TF) and its derivatives.ObjectiveThe ESIPT mechanism and photophysicalproperties of 3‐thiolflavone (3TF) and its derivatives 3NTF, 3ATF and 3OTF modified by ‐N(C2H5)2, ‐NH2 and ‐OCH3 groups were studied theoretically.MethodsDensity functional theory (DFT) and time‐dependent density functional theory (TD‐DFT) with PBE0 functional and 6‐31G(d, p) basis set.ResultsFor 3TF, 3NTF, 3ATF and 3OTF, the ESIPT processes are barrier‐less, and the barrier of ground‐state intramolecular proton transfer (GSIPT) reduces in the order of 3TF > 3OTF > 3ATF > 3NTF, as the electron‐donating ability of the substituent increases. When the electron‐donating groups are introduced, the absorption and fluorescence wavelengths of 3TF red‐shift and blue‐shift, respectively.ConclusionSubstituents with electron‐donating ability can regulate the ground‐state intramolecular proton transfer process and photophysical properties of 3TF.

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Theoretical Study on the Atom-Substituted Quinazoline Derivatives with Faint Emission as Potential Sunscreens

Cited by 8 publications

References 61 publications

An Integrated Polysaccharide Hydrogel with Versatile Fluorescence Responses through Noncovalent Reformation of Gel Aggregation and for Bioimaging

An Integrated Polysaccharide Hydrogel with Versatile Fluorescence Responses through Noncovalent Reformation of Gel Aggregation and for Bioimaging

Photoisomerization of “Partially Embedded Dihydropyridazine” with a Helical Structure

Regulating excited‐state intramolecular proton transfer behavior and fluorescent property of 3‐thiolflavone by electron‐donating ability: A time‐dependent density functional theory study

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