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Article

Carbazole-Based Colorimetric Anion Sensors †

Biological and Chemical Research Centre, Faculty of Chemistry, University of Warsaw, Żwirki i Wigury 101, 02-089 Warsaw, Poland
*
Author to whom correspondence should be addressed.
Dedicated to Professor Janusz Jurczak on the occasion of his 80th birthday.
Academic Editors: Marek Chmielewski, Patryk Niedbala and Maciej Majdecki
Molecules 2021, 26(11), 3205; https://doi.org/10.3390/molecules26113205
Received: 26 April 2021 / Revised: 18 May 2021 / Accepted: 24 May 2021 / Published: 27 May 2021
(This article belongs to the Special Issue In Honor of the 80th Birthday of Professor Janusz Jurczak)
Owing to their strong carbazole chromophore and fluorophore, as well as to their powerful and convergent hydrogen bond donors, 1,8-diaminocarbazoles are amongst the most attractive and synthetically versatile building blocks for the construction of anion receptors, sensors, and transporters. Aiming to develop carbazole-based colorimetric anion sensors, herein we describe the synthesis of 1,8-diaminocarbazoles substituted with strongly electron-withdrawing substituents, i.e., 3,6-dicyano and 3,6-dinitro. Both of these precursors were subsequently converted into model diamide receptors. Anion binding studies revealed that the new receptors exhibited significantly enhanced anion affinities, but also significantly increased acidities. We also found that rear substitution of 1,8-diamidocarbazole with two nitro groups shifted its absorption spectrum into the visible region and converted the receptor into a colorimetric anion sensor. The new sensor displayed vivid color and fluorescence changes upon addition of basic anions in wet dimethyl sulfoxide, but it was poorly selective; because of its enhanced acidity, the dominant receptor-anion interaction for most anions was proton transfer and, accordingly, similar changes in color were observed for all basic anions. The highly acidic and strongly binding receptors developed in this study may be applicable in organocatalysis or in pH-switchable anion transport through lipophilic membranes. View Full-Text
Keywords: supramolecular chemistry; anion recognition; anion receptors; anion sensors; colorimetric sensors supramolecular chemistry; anion recognition; anion receptors; anion sensors; colorimetric sensors
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MDPI and ACS Style

Maslowska-Jarzyna, K.; Korczak, M.L.; Wagner, J.A.; Chmielewski, M.J. Carbazole-Based Colorimetric Anion Sensors. Molecules 2021, 26, 3205. https://doi.org/10.3390/molecules26113205

AMA Style

Maslowska-Jarzyna K, Korczak ML, Wagner JA, Chmielewski MJ. Carbazole-Based Colorimetric Anion Sensors. Molecules. 2021; 26(11):3205. https://doi.org/10.3390/molecules26113205

Chicago/Turabian Style

Maslowska-Jarzyna, Krystyna, Maria L. Korczak, Jakub A. Wagner, and Michał J. Chmielewski. 2021. "Carbazole-Based Colorimetric Anion Sensors" Molecules 26, no. 11: 3205. https://doi.org/10.3390/molecules26113205

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