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. 2023 Jun 13;24(12):10084.
doi: 10.3390/ijms241210084.

Polyaromatic Hydrocarbon (PAH)-Based Aza-POPOPs: Synthesis, Photophysical Studies, and Nitroanalyte Sensing Abilities

Mohammed S Mohammed  1 , Igor S Kovalev  1 , Natalya V Slovesnova  1   2 , Leila K Sadieva  1   3 , Vadim A Platonov  1 , Alexander S Novikov  4   5 , Sougata Santra  1 , Julia E Morozova  6 , Grigory V Zyryanov  1   3 , Valery N Charushin  1   3 , Brindaban C Ranu  1   7
Affiliations

Polyaromatic Hydrocarbon (PAH)-Based Aza-POPOPs: Synthesis, Photophysical Studies, and Nitroanalyte Sensing Abilities

Mohammed S Mohammed et al. Int J Mol Sci. .

Abstract

1,4-Bis(5-phenyl-2-oxazolyl)benzene (POPOP) is a common scintillation fluorescent laser dye. In this manuscript, the synthesis of 2-Ar-5-(4-(4-Ar'-1H-1,2,3-triazol-1-yl)phenyl)-1,3,4-oxadiazoles (Ar, Ar' = Ph, naphtalenyl-2, pyrenyl-1, triphenilenyl-2), as PAH-based aza-analogues of POPOP, by means of Cu-catalyzed click reaction between 2-(4-azidophenyl)-5-Ar-1,3,4-oxadiazole and terminal ethynyl-substituted PAHs is reported. An investigation of the photophysical properties of the obtained products was carried out, and their sensory response to nitroanalytes was evaluated. In the case of pyrenyl-1-substituted aza-POPOP, dramatic fluorescence quenching by nitroanalytes was observed.

Keywords: 1,4-bis(5-phenyl-2-oxazolyl)benzene analogues; aza-POPOPs; chemosensors; click reactions; fluorescence quenching; nitro-explosives; photophysical studies.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
POPOP and its aza-analog core. POPOP = 1,4-Bis(5-phenyl-2-oxazolyl)benzene.
Scheme 1
Scheme 1
Synthesis of the azido components 2a,b. PTSA = p-Toluenesulfonic acid.
Scheme 2
Scheme 2
Synthesis of the POPOP analogues 3.
Figure 2
Figure 2
Absorption (A) and emission (B) spectra of POPOP and its aza-analogues 3 in CH2Cl2 (10−5 M). POPOP = 1,4-Bis(5-phenyl-2-oxazolyl)benzene.
Figure 3
Figure 3
Stern–Volmer plot (A) and overlayed graph (B) of the chemosensor 3g fluorescence quenching by PETN. PETN = Pentaerythritol tetranitrate.
Figure 4
Figure 4
Energy diagram of the PET quenching process. PET = photon-induced electron transfer; PETN = Pentaerythritol tetranitrate.
Figure 5
Figure 5
Normalized emission spectra of aza analogues POPOP. POPOP = 1,4-Bis(5-phenyl-2-oxazolyl)benzene.
Figure 6
Figure 6
Fluorescence quenching of chemosensor 3g by TNT. TNT = 2,4,6-Trinitrotoluene.
Figure 7
Figure 7
Fluorescence quenching of chemosensor 3g by DNT. DNT = 2,4-Dinitrotoluene.
Figure 8
Figure 8
Fluorescence quenching of chemosensor 3g by PETN. PETN = Pentaerythritol tetranitrate.
Figure 9
Figure 9
Overlayed graph of the chemosensor 3g quenching by DNT (UV-Vis). DNT = 2,4-Dinitrotoluene.
Figure 10
Figure 10
Overlayed graph of the chemosensor 3g quenching by DNT (Emission). DNT = 2,4-Dinitrotoluene.
Figure 11
Figure 11
Overlayed graph of the chemosensor 3g quenching by TNT (UV-Vis). TNT = 2,4,6-Trinitrotoluene.
Figure 12
Figure 12
Overlayed graph of the chemosensor 3g quenching by TNT (Emission). TNT = 2,4,6-Trinitrotoluene.
Figure 13
Figure 13
Overlayed graph of the chemosensor 3g quenching by PETN (UV-Vis). PETN = Pentaerythritol tetranitrate.
Figure 14
Figure 14
Overlayed graph of the chemosensor 3g quenching by PETN (Emission). PETN = Pentaerythritol tetranitrate.
Figure 15
Figure 15
Normalized emission and absorption spectra 3a.
Figure 16
Figure 16
Normalized emission and absorption spectra 3b.
Figure 17
Figure 17
Normalized emission and absorption spectra 3c.
Figure 18
Figure 18
Normalized emission and absorption spectra 3d.
Figure 19
Figure 19
Normalized emission and absorption spectra 3e.
Figure 20
Figure 20
Normalized emission and absorption spectra 3f.
Figure 21
Figure 21
Normalized emission and absorption spectra 3g.
Figure 22
Figure 22
Excitation spectrum 3a.
Figure 23
Figure 23
Excitation spectrum 3b.
Figure 24
Figure 24
Excitation spectrum 3c.
Figure 25
Figure 25
Excitation spectrum 3d.
Figure 26
Figure 26
Excitation spectrum 3e.
Figure 27
Figure 27
Excitation spectrum 3f.
Figure 28
Figure 28
Excitation spectrum 3g.
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