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Bola-type PAH-based fluorophores/chemosensors: Synthesis via an unusual clemmensen reduction and photophysical studies

2021; Elsevier BV; Volume: 420; Linguagem: Inglês

10.1016/j.jphotochem.2021.113466

1873-2666

Igor S. Коvalev, Olga S. Taniya, Leila К. Sadieva, Natalia N. Volkova, Артем С. Минин, K. V. Grzhegorzhevskii, Evgeny B. Gorbunov, Grigory V. Zyryanov, О. Н. Чупахин, Valery N. Charushin, Mikhail V. Tsurkan,

Supramolecular Chemistry and Complexes

Bola-type organic scaffolds are of key importance for application in a wide variety of fields. In this manuscript we wish to report our results on construction of polycyclic aromatic hydrocarbon (PAH, PAH = 9-antracenyl, 1-pyrenyl)-based bola-type fluorophores/chemosensors via an unusual Clemmensen reduction of the corresponding penta-1,4-dien-3-ones. In aqueous solutions the thus obtained bola-type molecules demonstrate intensive excimer emission at 500 nm, as well as well-pronounced "turn-off" fluorescence response towards common nitro-explosive components, such as 2,4-dinitrotoluene (DNT) and 2,4,6-trinitrotoluene (TNT), as well as, hard-to-detect pentaerythritol tetranitrate (PETN).