(1-(4-(5-Phenyl-1,3,4-oxadiazol-2-yl)phenyl)-1 H-1,2,3-triazol-4-yl)-methylenyls α,ω-Bisfunctionalized 3- and 4-PEG: Synthesis and Photophysical Studies

Mohammed S Mohammed; Igor S Kovalev; Natalya V Slovesnova; Leila K Sadieva; Vadim A Platonov; Grigory A Kim; Rammohan Aluru; Alexander S Novikov; Olga S Taniya; Valery N Charushin

doi:10.3390/molecules28135256

(1-(4-(5-Phenyl-1,3,4-oxadiazol-2-yl)phenyl)-1 H-1,2,3-triazol-4-yl)-methylenyls α,ω-Bisfunctionalized 3- and 4-PEG: Synthesis and Photophysical Studies

Molecules. 2023 Jul 6;28(13):5256. doi: 10.3390/molecules28135256.

Authors

Mohammed S Mohammed¹, Igor S Kovalev¹, Natalya V Slovesnova^{1

2}, Leila K Sadieva¹, Vadim A Platonov¹, Grigory A Kim^{3

4}, Rammohan Aluru¹, Alexander S Novikov^{5

6}, Olga S Taniya¹, Valery N Charushin^{1

3}

Affiliations

¹ Chemical Engineering Institute, Ural Federal University, 19 Mira St., 620002 Yekaterinburg, Russia.
² Department of Pharmacy and Chemistry, Ural Medical University, 3 Repina St., 620028 Yekaterinburg, Russia.
³ I. Ya. Postovsky Institute of Organic Synthesis of RAS (Ural Division), 22/20 S. Kovalevskoy/Akademicheskaya St., 620137 Yekaterinburg, Russia.
⁴ Institute of Natural Sciences and Mathematics, Ural Federal University, 19 Mira St., 620002 Yekaterinburg, Russia.
⁵ Institute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya Nab., 199034 Saint Petersburg, Russia.
⁶ Research Institute of Chemistry, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya Street, 117198 Moscow, Russia.

Abstract

Two new azaheterocycle-based bolas, such as (1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)-1H-1,2,3-triazol-4-yl)-methylenyls α,ω-bisfunctionalized PEGs, were prepared via Cu-catalyzed click reaction between 2-(4-azidophenyl)-5-(aryl)-oxadiazole-1,3,4 and terminal ethynyls derived from PEG-3 and PEG-4. Due to the presence of two heteroaromatic cores and a PEG linker, these bola molecules are considered as promising fluorescent chemosensors for electron-deficient species. As a result of a well-pronounced "turn-off" fluorescence response towards common nitro-explosive components, such as 2,4-dinitrotoluene (DNT) and 2,4,6-trinitrotoluene (TNT), hard-to-detect pentaerythritol tetranitrate (PETN), as well as Hg²⁺ cation was observed.

Keywords: Hg2+; PEGs; bola molecules; fluorescence; fluorescence quenching; nitro-explosive components; oxadiazole; pentaerythritol tetranitrate; sensor; “click” reactions.

MeSH terms

Explosive Agents*
Trinitrotoluene*

Substances

Explosive Agents
Trinitrotoluene

Grants and funding

075-15-2022-1118/Ministry of Science and Higher Education of the Russian Federation