Highly fluorescent sensing of nitroaromatic explosives in aqueous media using pyrene-linked PBEMA microspheres

Hamza Turhan; Ece Tukenmez; Bunyamin Karagoz; Niyazi Bicak

doi:10.1016/j.talanta.2017.10.061

Highly fluorescent sensing of nitroaromatic explosives in aqueous media using pyrene-linked PBEMA microspheres

Hamza Turhan, Ece Tukenmez, Bunyamin Karagoz^*, Niyazi Bicak

^*Corresponding author for this work

Department of Chemistry

Istanbul Technical University

Research output: Contribution to journal › Article › peer-review

40 Citations (Scopus)

Abstract

Crosslinked 2-bromoethyl methacrylate polymer (PBEMA) was prepared in micro-spherical form (2–5 µm) by precipitation polymerization methodology. The bromide substituent was substituted with an azide group, which was then coupled with 1-[(2-Propynyloxy)methyl]pyrene] via alkyne-azide click chemistry. The pyrene-linked microspheres showed an intense green-blue excimer emission with a maximum at 480 nm, implying π−π stacking between the pyrene moieties on the microsphere surfaces. This fluorescence emission is extremely sensitive to the aromatic nitro compounds. So that the green-blue light fades immediately upon addition of trace amounts of 2,4,6-trinitrotoluene (TNT), 2,4-dinitrotoluene (DNT) and 2,4,6-trinitro phenol (TNP) in 100% aqueous media. Stern-Volmer plots were employed for comparison of their fluorescence quenching effects. The plots revealed Stern-Volmer constants of 1.33 × 10⁵, 2.451 × 10⁵ and 1.076 × 10⁵ M⁻¹ for TNT, TNP and DNT, respectively. Furthermore, it has been observed that, the microspheres can be reused several times, without losing excimer emission properties.

Original language	English
Pages (from-to)	107-114
Number of pages	8
Journal	Talanta
Volume	179
DOIs	https://doi.org/10.1016/j.talanta.2017.10.061
Publication status	Published - 1 Mar 2018

Bibliographical note

Publisher Copyright:
© 2017 Elsevier B.V.

Funding

The authors are thankful to Istanbul Technical University Graduate School of Science Engineering and Technology ( 39920 ) for the financial support. We are also grateful to Prof. Dr. Ismail Yilmaz for his helps in taking fluorescence spectra. We are also thankful to YTU Department of Chemistry for fluorescence lifetime measurement.

Funders	Funder number
Istanbul Technical University Graduate School of Science Engineering and Technology	39920

Keywords

2-Bromoethyl methacrylate (BEMA)
Aqueous phase
Click chemistry
Fluorescence quenching
Nitroaromatic detection
Pyrene

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title = "Highly fluorescent sensing of nitroaromatic explosives in aqueous media using pyrene-linked PBEMA microspheres",

abstract = "Crosslinked 2-bromoethyl methacrylate polymer (PBEMA) was prepared in micro-spherical form (2–5 µm) by precipitation polymerization methodology. The bromide substituent was substituted with an azide group, which was then coupled with 1-[(2-Propynyloxy)methyl]pyrene] via alkyne-azide click chemistry. The pyrene-linked microspheres showed an intense green-blue excimer emission with a maximum at 480 nm, implying π−π stacking between the pyrene moieties on the microsphere surfaces. This fluorescence emission is extremely sensitive to the aromatic nitro compounds. So that the green-blue light fades immediately upon addition of trace amounts of 2,4,6-trinitrotoluene (TNT), 2,4-dinitrotoluene (DNT) and 2,4,6-trinitro phenol (TNP) in 100% aqueous media. Stern-Volmer plots were employed for comparison of their fluorescence quenching effects. The plots revealed Stern-Volmer constants of 1.33 × 105, 2.451 × 105 and 1.076 × 105 M−1 for TNT, TNP and DNT, respectively. Furthermore, it has been observed that, the microspheres can be reused several times, without losing excimer emission properties.",

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author = "Hamza Turhan and Ece Tukenmez and Bunyamin Karagoz and Niyazi Bicak",

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AU - Turhan, Hamza

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AU - Bicak, Niyazi

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N2 - Crosslinked 2-bromoethyl methacrylate polymer (PBEMA) was prepared in micro-spherical form (2–5 µm) by precipitation polymerization methodology. The bromide substituent was substituted with an azide group, which was then coupled with 1-[(2-Propynyloxy)methyl]pyrene] via alkyne-azide click chemistry. The pyrene-linked microspheres showed an intense green-blue excimer emission with a maximum at 480 nm, implying π−π stacking between the pyrene moieties on the microsphere surfaces. This fluorescence emission is extremely sensitive to the aromatic nitro compounds. So that the green-blue light fades immediately upon addition of trace amounts of 2,4,6-trinitrotoluene (TNT), 2,4-dinitrotoluene (DNT) and 2,4,6-trinitro phenol (TNP) in 100% aqueous media. Stern-Volmer plots were employed for comparison of their fluorescence quenching effects. The plots revealed Stern-Volmer constants of 1.33 × 105, 2.451 × 105 and 1.076 × 105 M−1 for TNT, TNP and DNT, respectively. Furthermore, it has been observed that, the microspheres can be reused several times, without losing excimer emission properties.

AB - Crosslinked 2-bromoethyl methacrylate polymer (PBEMA) was prepared in micro-spherical form (2–5 µm) by precipitation polymerization methodology. The bromide substituent was substituted with an azide group, which was then coupled with 1-[(2-Propynyloxy)methyl]pyrene] via alkyne-azide click chemistry. The pyrene-linked microspheres showed an intense green-blue excimer emission with a maximum at 480 nm, implying π−π stacking between the pyrene moieties on the microsphere surfaces. This fluorescence emission is extremely sensitive to the aromatic nitro compounds. So that the green-blue light fades immediately upon addition of trace amounts of 2,4,6-trinitrotoluene (TNT), 2,4-dinitrotoluene (DNT) and 2,4,6-trinitro phenol (TNP) in 100% aqueous media. Stern-Volmer plots were employed for comparison of their fluorescence quenching effects. The plots revealed Stern-Volmer constants of 1.33 × 105, 2.451 × 105 and 1.076 × 105 M−1 for TNT, TNP and DNT, respectively. Furthermore, it has been observed that, the microspheres can be reused several times, without losing excimer emission properties.

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KW - Aqueous phase

KW - Click chemistry

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KW - Nitroaromatic detection

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Highly fluorescent sensing of nitroaromatic explosives in aqueous media using pyrene-linked PBEMA microspheres

Abstract

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Keywords

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