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Benzimidazole as a structural unit in optical chemical sensors: the hidden properties of a biologically privileged heterocyclic scaffold (CROSBI ID 650125)

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Horak, Ema ; Hranjec, Marijana ; Vianello, Robert ; Perin, Nataša ; Murković Steinberg, Ivana Benzimidazole as a structural unit in optical chemical sensors: the hidden properties of a biologically privileged heterocyclic scaffold // 12th International Symposium on Macrocyclic and Supramolecular Chemistry in conjunction with ISACS: Book of Abstracts, Cambridge, 02.-06.07.2017.. 2017. str. 301-x

Podaci o odgovornosti

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

engleski

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

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.

benzimidazole ; sensors

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Podaci o prilogu

301-x.

2017.

objavljeno

Podaci o matičnoj publikaciji

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

Podaci o skupu

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

poster

02.07.2017-06.07.2017

Cambridge, Ujedinjeno Kraljevstvo

Povezanost rada

Kemija