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The Influence of Substituents on 4-Amino-1,2,4-Triazole Luminescence: A Combined Crystallographic and Spectroscopic Study.

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Title: The Influence of Substituents on 4-Amino-1,2,4-Triazole Luminescence: A Combined Crystallographic and Spectroscopic Study.
Authors: Shi, Jia-Yi1 (AUTHOR) 1470219399@qq.com, Shi, Ye1 (AUTHOR) 446657113@qq.com, Ya, Meng-Yu1 (AUTHOR) 2294138345@qq.com, Tang, Gui-Mei1 (AUTHOR) tgm@qlu.edu.cn, Wang, Yong-Tao2 (AUTHOR) ceswyt@qlu.edu.cn
Source: Journal of Fluorescence. Mar2026, Vol. 36 Issue 3, p2291-2307. 17p.
Subjects: Luminescence, Stacking interactions, Optical properties, Crystallography, Fluorescence yield, Triazole derivatives, Intermolecular interactions, Spectrometry
Abstract: To explore new luminescent materials, two novel luminescent salts, [HAD]⁺BSA⁻∙methanol (1) and [HAD]⁺TSA⁻∙methanol (2), incorporating the 4-amino-1,2,4-triazole functional moiety (AD = 4,4'-(4-amino-4H-1,2,4-triazole-3,5-diyl)dianiline), were successfully synthesized through reactions with benzenesulfonic acid and p-toluenesulfonic acid, respectively. Comprehensive characterization via single-crystal X-ray diffraction, FT-IR, UV–Vis, and PXRD revealed distinct photophysical properties governed by their supramolecular architectures. Solid-state emission studies demonstrated blue-shifted maxima at 443 nm for salt 1 and 449 nm for salt 2 compared to the free AD ligand (457 nm), corresponding to shifts of 14 nm and 8 nm, respectively. This emission modulation directly correlates with π∙∙∙π stacking interactions, where shorter stacking distances in salt 1 (3.878 Å) versus salt 2 (4.406 Å) enhance intermolecular electronic coupling. Hirshfeld surface analysis confirmed stronger C∙∙∙H contacts in salt 1, consistent with its more pronounced stacking interactions and shorter emission wavelength. The lifetimes can be observed to 1.41, 0.96 and 0.90 ns, while the quantum yields of compounds can be found to be 0.20, 0.26 and 0.38 for AD, 1 and 2, respectively. The study establishes definitive structure–property relationships, demonstrating that strategic manipulation of weak intermolecular forces provides an effective pathway for engineering luminescent properties in triazole-based materials through crystal engineering. Highlights: • Two new salts containing 4-amino-1,2,4-triazole group have been obtained. • The luminescent properties can be affected by the substituents. • The O∙∙∙H/H∙∙∙O and N∙∙∙H/H∙∙∙N close contacts can account for the melting points of compounds. • The emission maxima and the quantum yields are proportional to the C∙∙∙H close contacts. The proposed artwork would conceptually illustrate the synthesis of two novel 4-amino-1,2,4-triazole salts (1 and 2) from the AD ligand and their respective sulfonic acids, then clearly depict their distinct crystal packing arrangements with emphasis on the key π-π stacking distances (3.878 Å for 1 and 4.406 Å for 2). This structural analysis should be directly linked to Hirshfeld surface data, highlighting the differing C/N/O∙∙∙H contact percentages, which subsequently correlate to the measured photophysical outcomes: the blue-shifted solid-state emission maxima (443 nm for 1 and 449 nm for 2, versus 457 nm for the free ligand), the shorter fluorescence lifetimes (0.96 ns and 0.90 ns for the salts, versus 1.41 ns for the ligand), and the higher quantum yields (0.38 and 0.26 for the salts, versus 0.20 for the ligand). The visual narrative would thus effectively convey how deliberate modification of intermolecular interactions serves as a powerful strategy for tuning the luminescent properties of these crystalline materials. [ABSTRACT FROM AUTHOR]
Copyright of Journal of Fluorescence 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.)
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DbLabel: Engineering Source
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  Data: The Influence of Substituents on 4-Amino-1,2,4-Triazole Luminescence: A Combined Crystallographic and Spectroscopic Study.
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  Data: <searchLink fieldCode="AR" term="%22Shi%2C+Jia-Yi%22">Shi, Jia-Yi</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> 1470219399@qq.com</i><br /><searchLink fieldCode="AR" term="%22Shi%2C+Ye%22">Shi, Ye</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> 446657113@qq.com</i><br /><searchLink fieldCode="AR" term="%22Ya%2C+Meng-Yu%22">Ya, Meng-Yu</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> 2294138345@qq.com</i><br /><searchLink fieldCode="AR" term="%22Tang%2C+Gui-Mei%22">Tang, Gui-Mei</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> tgm@qlu.edu.cn</i><br /><searchLink fieldCode="AR" term="%22Wang%2C+Yong-Tao%22">Wang, Yong-Tao</searchLink><relatesTo>2</relatesTo> (AUTHOR)<i> ceswyt@qlu.edu.cn</i>
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  Data: <searchLink fieldCode="JN" term="%22Journal+of+Fluorescence%22">Journal of Fluorescence</searchLink>. Mar2026, Vol. 36 Issue 3, p2291-2307. 17p.
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  Data: <searchLink fieldCode="DE" term="%22Luminescence%22">Luminescence</searchLink><br /><searchLink fieldCode="DE" term="%22Stacking+interactions%22">Stacking interactions</searchLink><br /><searchLink fieldCode="DE" term="%22Optical+properties%22">Optical properties</searchLink><br /><searchLink fieldCode="DE" term="%22Crystallography%22">Crystallography</searchLink><br /><searchLink fieldCode="DE" term="%22Fluorescence+yield%22">Fluorescence yield</searchLink><br /><searchLink fieldCode="DE" term="%22Triazole+derivatives%22">Triazole derivatives</searchLink><br /><searchLink fieldCode="DE" term="%22Intermolecular+interactions%22">Intermolecular interactions</searchLink><br /><searchLink fieldCode="DE" term="%22Spectrometry%22">Spectrometry</searchLink>
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  Label: Abstract
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  Data: To explore new luminescent materials, two novel luminescent salts, [HAD]⁺BSA⁻∙methanol (1) and [HAD]⁺TSA⁻∙methanol (2), incorporating the 4-amino-1,2,4-triazole functional moiety (AD = 4,4'-(4-amino-4H-1,2,4-triazole-3,5-diyl)dianiline), were successfully synthesized through reactions with benzenesulfonic acid and p-toluenesulfonic acid, respectively. Comprehensive characterization via single-crystal X-ray diffraction, FT-IR, UV–Vis, and PXRD revealed distinct photophysical properties governed by their supramolecular architectures. Solid-state emission studies demonstrated blue-shifted maxima at 443 nm for salt 1 and 449 nm for salt 2 compared to the free AD ligand (457 nm), corresponding to shifts of 14 nm and 8 nm, respectively. This emission modulation directly correlates with π∙∙∙π stacking interactions, where shorter stacking distances in salt 1 (3.878 Å) versus salt 2 (4.406 Å) enhance intermolecular electronic coupling. Hirshfeld surface analysis confirmed stronger C∙∙∙H contacts in salt 1, consistent with its more pronounced stacking interactions and shorter emission wavelength. The lifetimes can be observed to 1.41, 0.96 and 0.90 ns, while the quantum yields of compounds can be found to be 0.20, 0.26 and 0.38 for AD, 1 and 2, respectively. The study establishes definitive structure–property relationships, demonstrating that strategic manipulation of weak intermolecular forces provides an effective pathway for engineering luminescent properties in triazole-based materials through crystal engineering. Highlights: • Two new salts containing 4-amino-1,2,4-triazole group have been obtained. • The luminescent properties can be affected by the substituents. • The O∙∙∙H/H∙∙∙O and N∙∙∙H/H∙∙∙N close contacts can account for the melting points of compounds. • The emission maxima and the quantum yields are proportional to the C∙∙∙H close contacts. The proposed artwork would conceptually illustrate the synthesis of two novel 4-amino-1,2,4-triazole salts (1 and 2) from the AD ligand and their respective sulfonic acids, then clearly depict their distinct crystal packing arrangements with emphasis on the key π-π stacking distances (3.878 Å for 1 and 4.406 Å for 2). This structural analysis should be directly linked to Hirshfeld surface data, highlighting the differing C/N/O∙∙∙H contact percentages, which subsequently correlate to the measured photophysical outcomes: the blue-shifted solid-state emission maxima (443 nm for 1 and 449 nm for 2, versus 457 nm for the free ligand), the shorter fluorescence lifetimes (0.96 ns and 0.90 ns for the salts, versus 1.41 ns for the ligand), and the higher quantum yields (0.38 and 0.26 for the salts, versus 0.20 for the ligand). The visual narrative would thus effectively convey how deliberate modification of intermolecular interactions serves as a powerful strategy for tuning the luminescent properties of these crystalline materials. [ABSTRACT FROM AUTHOR]
– Name: AbstractSuppliedCopyright
  Label:
  Group: Ab
  Data: <i>Copyright of Journal of Fluorescence 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.)
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RecordInfo BibRecord:
  BibEntity:
    Identifiers:
      – Type: doi
        Value: 10.1007/s10895-025-04696-y
    Languages:
      – Code: eng
        Text: English
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      Pagination:
        PageCount: 17
        StartPage: 2291
    Subjects:
      – SubjectFull: Luminescence
        Type: general
      – SubjectFull: Stacking interactions
        Type: general
      – SubjectFull: Optical properties
        Type: general
      – SubjectFull: Crystallography
        Type: general
      – SubjectFull: Fluorescence yield
        Type: general
      – SubjectFull: Triazole derivatives
        Type: general
      – SubjectFull: Intermolecular interactions
        Type: general
      – SubjectFull: Spectrometry
        Type: general
    Titles:
      – TitleFull: The Influence of Substituents on 4-Amino-1,2,4-Triazole Luminescence: A Combined Crystallographic and Spectroscopic Study.
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            NameFull: Shi, Jia-Yi
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            NameFull: Shi, Ye
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              Text: Mar2026
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              Y: 2026
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