Near-infrared benzodiazoles as small molecule environmentally-sensitive fluorophores

Fabio de Moliner, Ina Biazruchka, Karolina Konsewicz, Sam Benson, Suraj Singh, Jun-Seok Lee, Marc Vendrell

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Front. Chem. Sci. Eng. ›› 2022, Vol. 16 ›› Issue (1) : 128-135. DOI: 10.1007/s11705-021-2080-8
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Near-infrared benzodiazoles as small molecule environmentally-sensitive fluorophores

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Abstract

The development of fluorophores emitting in the near-infrared spectral window has gained increased attention given their suitable features for biological imaging. In this work, we have optimised a general and straightforward synthetic approach to prepare a small library of near-infrared-emitting C-bridged nitrobenzodiazoles using commercial precursors. C-bridged benzodiazoles have low molecular weight and neutral character as important features that are not common in most near-infrared dyes. We have investigated their fluorescence response in the presence of a wide array of 60 different biomolecules and identified compound 3i as a potential chemosensor to discriminate between Fe2+ and Fe3+ ions in aqueous media.

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Keywords

fluorescence / probes / iron / screening / library

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Fabio de Moliner, Ina Biazruchka, Karolina Konsewicz, Sam Benson, Suraj Singh, Jun-Seok Lee, Marc Vendrell. Near-infrared benzodiazoles as small molecule environmentally-sensitive fluorophores. Front. Chem. Sci. Eng., 2022, 16(1): 128‒135 https://doi.org/10.1007/s11705-021-2080-8

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Acknowledgments

The authors acknowledge funding from Medical Research Scotland (Sam Benson: 879-2015) and an ERC Consolidator Grant (DYNAFLUORS, Marc Vendrell: 771443). This work was also supported by National Research Foundation funded by the Ministry of Science, ICT & Future Planning, South Korea (Jun-Seok Lee: NRF- 2018M3A9H4079286, NRF-2020R1A2C2004422).

Electronic Supplementary Material

Supplementary material is available in the online version of this article at https://dx.doi.org/10.1007/s11705-021-2080-8 and is accessible for authorized users.

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2021 The Author(s) 2021. This article is published with open access at link.springer.com and journal.hep.com.cn
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