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

Mohammed S Mohammed; Igor S Kovalev; Natalya V Slovesnova; Leila K Sadieva; Vadim A Platonov; Alexander S Novikov; Sougata Santra; Julia E Morozova; Grigory V Zyryanov; Valery N Charushin; Brindaban C Ranu

doi:10.3390/ijms241210084

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

Int J Mol Sci. 2023 Jun 13;24(12):10084. doi: 10.3390/ijms241210084.

Authors

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

2}, Leila K Sadieva^{1

3}, Vadim A Platonov¹, Alexander S Novikov^{4

5}, Sougata Santra¹, Julia E Morozova⁶, Grigory V Zyryanov^{1

3}, Valery N Charushin^{1

3}, Brindaban C Ranu^{1

7}

Affiliations

¹ Department of Organic and Biomolecular Chemistry, 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 Chemistry, Saint Petersburg State University, Universitetskaya Nab., 7/9, 199034 Saint Petersburg, Russia.
⁵ Research Institute of Chemistry, Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya St., 6, 117198 Moscow, Russia.
⁶ Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, Arbuzov Str. 8, 420088 Kazan, Russia.
⁷ School of Chemical Sciences, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700032, India.

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.

MeSH terms

Fluorescence
Hydrocarbons*

Substances

Hydrocarbons

Grants and funding

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