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

Author:

Mohammed Mohammed S.1,Kovalev Igor S.1ORCID,Slovesnova Natalya V.12,Sadieva Leila K.13ORCID,Platonov Vadim A.1,Novikov Alexander S.45ORCID,Santra Sougata1,Morozova Julia E.6,Zyryanov Grigory V.13,Charushin Valery N.13ORCID,Ranu Brindaban C.17

Affiliation:

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.

Funder

Ministry of Science and Higher Education of the Russian Federation

Publisher

MDPI AG

Subject

Inorganic Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Computer Science Applications,Spectroscopy,Molecular Biology,General Medicine,Catalysis

Reference76 articles.

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