Naslov
Benzimidazole as a structural unit in optical chemical sensors: the hidden properties of a biologically privileged heterocyclic scaffold

Autori
Horak, Ema ; Hranjec, Marijana ; Vianello, Robert ; Perin, Nataša ; Murković Steinberg, Ivana

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
12th International Symposium on Macrocyclic and Supramolecular Chemistry in conjunction with ISACS: Book of Abstracts, Cambridge, 02.-06.07.2017. / - , 2017

Skup
12th International Symposium on Macrocyclic and Supramolecular Chemistry in conjunction with ISACS

Mjesto i datum
Cambridge, Ujedinjeno Kraljevstvo, 02.07.2017. - 06.07.2017

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
benzimidazol ; senzori
(benzimidazole ; sensors)

Sažetak
Benzimidazole (BI) derivatives are structurally similar to naturally occurring nucleotides, a fact that enables their use as scaffolds in biologically active organic synthetic compounds. The BI moiety is therapeutically active and is widely used in drug discovery and medicinal research [1]. Its many structure- related properties such as electron accepting ability, π bridging, chromogenic pH sensitivity/switching, and metal-ion chelating properties also make BI an exceptional structural candidate for optical chemical sensors. BI can serve as a multifunctional unit in heteroaromatic molecular systems for optoelectronics and non-linear optics (NLO), photovoltaics, and in sensing and bioimaging. Here, several classes of D-π-A chemo-sensing molecules based on BI have been studied in order to create a library of structure-property relationships, and to evaluate the potential application of these molecules in optical sensing. BI based acrylonitrile dyes [2], benzimidazo[1, 2-a]quinolines [3] and Schiff bases are presented as candidate pH sensitive probes and sensors for metal ions. The examined compounds show excellent optical properties, including strong fluorescence in the visible region, and protonation-deprotonation equilibria associated with drastic changes in photophysical properties due to charge-transfer reactions in the excited state. These findings have been leveraged in the development of novel functional materials including thin polymer films for optical sensing. Several of the compounds formed self-assembled organic nanostructures, and exhibited aggregation induced emission (AIE). The AIE phenomenon is successfully demonstrated as a mechanism for the reversible optical sensing of pH.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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