Fluorescence quenching and electronic interaction of (S)-5-(dimethylamino)-N-(1-phenylethyl)naphthalene-1-sulfonamide for selective nitroaromatic detection and DFT study.
Saved in:
| Title: | Fluorescence quenching and electronic interaction of (S)-5-(dimethylamino)-N-(1-phenylethyl)naphthalene-1-sulfonamide for selective nitroaromatic detection and DFT study. |
|---|---|
| Authors: | Muhammad, Imran1 (AUTHOR) imrantotkay@gmail.com, Han, Rong2 (AUTHOR), Ren, Tie Zhen1 (AUTHOR) rtz@xju.edu.cn, Zha, Chun-Mei1 (AUTHOR), Shahzad, Adnan3 (AUTHOR), Ullah, Ihsan3 (AUTHOR) |
| Source: | Structural Chemistry. Jun2026, Vol. 37 Issue 3, p1265-1279. 15p. |
| Subjects: | Fluorescence quenching, Nitroaromatic compounds, Photoinduced electron transfer, Density functional theory, Fluorophores, Hydrogen bonding, Solvatochromism |
| Abstract: | The development of selective and sensitive sensing systems for nitroaromatics (NACs) is critical for environmental monitoring. In this study, we investigate the structural and electronic properties of (S)-5-(Dimethylamino)-N-(1-phenylethyl)naphthalene-1-sulfonamide (D) using density functional theory (DFT) and fluorescence spectroscopy. D exhibits strong non-covalent interactions primarily hydrogen bonding with NACs, including metronidazole (MNZ), 4-nitrophenol (4NP), 2-nitrophenol (2NP), picric acid (PA), chloro-nitrobenzene (ClNB), and nitrobenzene (NB). Frontier molecular orbital, TDOS/PDOS, and electrostatic potential analyses reveal that electron-rich sulfonyl oxygens (O-p) in D preferentially engage in hydrogen bonding with analyte protons (H–s). This interaction significantly reduces the HOMO–LUMO gap (4.15 to 3.25 eV for D–MNZ) and increases electrophilicity (up to 5.06 eV for D–MNZ), supporting enhanced electron-accepting ability. Complexation energies further confirm strong binding, especially with MNZ (− 2.57 eV). Experimentally, D exhibits pronounced solvatochromism, with emission maxima shifting from 477 nm in n-hexane to 553 nm in water, and fluorescence intensity peaking at 369 a.u. in DMF; notably, low fluorescence intensity in water and irregular responses in n-hexane and cyclohexane. To understand these observations at the molecular level, TDDFT calculations were performed using the COSMO solvation model. Simulations confirm solvent influence and reveal that complexation with NACs in acetonitrile induces a red shift in emission (~ 480 nm) alongside substantial fluorescence quenching. This effect is most pronounced for MNZ (3.99 × 10−⁶), 4NP (2.19 × 10−5), 2NP (1.36 × 10−4), and PA (1.37 × 10−4), consistent with strong hydrogen bonding and photoinduced electron transfer. Together, these experimental and theoretical findings underscore the high selectivity and environmental responsiveness of D as a fluorophore for the detection of electron-deficient NACs analytes. [ABSTRACT FROM AUTHOR] |
| Copyright of Structural Chemistry is the property of Springer Nature and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.) | |
| Database: | Engineering Source |
| FullText | Text: Availability: 0 |
|---|---|
| Header | DbId: egs DbLabel: Engineering Source An: 193807131 AccessLevel: 6 PubType: Academic Journal PubTypeId: academicJournal PreciseRelevancyScore: 0 |
| IllustrationInfo | |
| Items | – Name: Title Label: Title Group: Ti Data: Fluorescence quenching and electronic interaction of (S)-5-(dimethylamino)-N-(1-phenylethyl)naphthalene-1-sulfonamide for selective nitroaromatic detection and DFT study. – Name: Author Label: Authors Group: Au Data: <searchLink fieldCode="AR" term="%22Muhammad%2C+Imran%22">Muhammad, Imran</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> imrantotkay@gmail.com</i><br /><searchLink fieldCode="AR" term="%22Han%2C+Rong%22">Han, Rong</searchLink><relatesTo>2</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Ren%2C+Tie+Zhen%22">Ren, Tie Zhen</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> rtz@xju.edu.cn</i><br /><searchLink fieldCode="AR" term="%22Zha%2C+Chun-Mei%22">Zha, Chun-Mei</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Shahzad%2C+Adnan%22">Shahzad, Adnan</searchLink><relatesTo>3</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Ullah%2C+Ihsan%22">Ullah, Ihsan</searchLink><relatesTo>3</relatesTo> (AUTHOR) – Name: TitleSource Label: Source Group: Src Data: <searchLink fieldCode="JN" term="%22Structural+Chemistry%22">Structural Chemistry</searchLink>. Jun2026, Vol. 37 Issue 3, p1265-1279. 15p. – Name: Subject Label: Subjects Group: Su Data: <searchLink fieldCode="DE" term="%22Fluorescence+quenching%22">Fluorescence quenching</searchLink><br /><searchLink fieldCode="DE" term="%22Nitroaromatic+compounds%22">Nitroaromatic compounds</searchLink><br /><searchLink fieldCode="DE" term="%22Photoinduced+electron+transfer%22">Photoinduced electron transfer</searchLink><br /><searchLink fieldCode="DE" term="%22Density+functional+theory%22">Density functional theory</searchLink><br /><searchLink fieldCode="DE" term="%22Fluorophores%22">Fluorophores</searchLink><br /><searchLink fieldCode="DE" term="%22Hydrogen+bonding%22">Hydrogen bonding</searchLink><br /><searchLink fieldCode="DE" term="%22Solvatochromism%22">Solvatochromism</searchLink> – Name: Abstract Label: Abstract Group: Ab Data: The development of selective and sensitive sensing systems for nitroaromatics (NACs) is critical for environmental monitoring. In this study, we investigate the structural and electronic properties of (S)-5-(Dimethylamino)-N-(1-phenylethyl)naphthalene-1-sulfonamide (D) using density functional theory (DFT) and fluorescence spectroscopy. D exhibits strong non-covalent interactions primarily hydrogen bonding with NACs, including metronidazole (MNZ), 4-nitrophenol (4NP), 2-nitrophenol (2NP), picric acid (PA), chloro-nitrobenzene (ClNB), and nitrobenzene (NB). Frontier molecular orbital, TDOS/PDOS, and electrostatic potential analyses reveal that electron-rich sulfonyl oxygens (O-p) in D preferentially engage in hydrogen bonding with analyte protons (H–s). This interaction significantly reduces the HOMO–LUMO gap (4.15 to 3.25 eV for D–MNZ) and increases electrophilicity (up to 5.06 eV for D–MNZ), supporting enhanced electron-accepting ability. Complexation energies further confirm strong binding, especially with MNZ (− 2.57 eV). Experimentally, D exhibits pronounced solvatochromism, with emission maxima shifting from 477 nm in n-hexane to 553 nm in water, and fluorescence intensity peaking at 369 a.u. in DMF; notably, low fluorescence intensity in water and irregular responses in n-hexane and cyclohexane. To understand these observations at the molecular level, TDDFT calculations were performed using the COSMO solvation model. Simulations confirm solvent influence and reveal that complexation with NACs in acetonitrile induces a red shift in emission (~ 480 nm) alongside substantial fluorescence quenching. This effect is most pronounced for MNZ (3.99 × 10−⁶), 4NP (2.19 × 10−5), 2NP (1.36 × 10−4), and PA (1.37 × 10−4), consistent with strong hydrogen bonding and photoinduced electron transfer. Together, these experimental and theoretical findings underscore the high selectivity and environmental responsiveness of D as a fluorophore for the detection of electron-deficient NACs analytes. [ABSTRACT FROM AUTHOR] – Name: AbstractSuppliedCopyright Label: Group: Ab Data: <i>Copyright of Structural Chemistry is the property of Springer Nature and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.) |
| PLink | https://search.ebscohost.com/login.aspx?direct=true&site=eds-live&db=egs&AN=193807131 |
| RecordInfo | BibRecord: BibEntity: Identifiers: – Type: doi Value: 10.1007/s11224-025-02620-5 Languages: – Code: eng Text: English PhysicalDescription: Pagination: PageCount: 15 StartPage: 1265 Subjects: – SubjectFull: Fluorescence quenching Type: general – SubjectFull: Nitroaromatic compounds Type: general – SubjectFull: Photoinduced electron transfer Type: general – SubjectFull: Density functional theory Type: general – SubjectFull: Fluorophores Type: general – SubjectFull: Hydrogen bonding Type: general – SubjectFull: Solvatochromism Type: general Titles: – TitleFull: Fluorescence quenching and electronic interaction of (S)-5-(dimethylamino)-N-(1-phenylethyl)naphthalene-1-sulfonamide for selective nitroaromatic detection and DFT study. Type: main BibRelationships: HasContributorRelationships: – PersonEntity: Name: NameFull: Muhammad, Imran – PersonEntity: Name: NameFull: Han, Rong – PersonEntity: Name: NameFull: Ren, Tie Zhen – PersonEntity: Name: NameFull: Zha, Chun-Mei – PersonEntity: Name: NameFull: Shahzad, Adnan – PersonEntity: Name: NameFull: Ullah, Ihsan IsPartOfRelationships: – BibEntity: Dates: – D: 01 M: 06 Text: Jun2026 Type: published Y: 2026 Identifiers: – Type: issn-print Value: 10400400 Numbering: – Type: volume Value: 37 – Type: issue Value: 3 Titles: – TitleFull: Structural Chemistry Type: main |
| ResultId | 1 |
