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A molecular design for a turn-off NIR fluoride chemosensor

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Abstract

We designed a turn-off near-infrared fluorescent fluoride chemosensor NIR-BODIPY-Si through the density functional theory/time-dependent functional theory calculations. In the designed sensor, the tert-butyldimethylsilyloxy moiety responses to the fluoride-triggered desilylation process, and the BODIPY dye serves as fluorophore. The molecular design firstly showed that the possibility of photoinduced electron transfer is low/high in NIR-BODIPY-Si/NIR-BODIPY-O (the desilylation product), thus referring that the fluorescence sensing mechanism is a photoinduced electron transfer mechanism that quenched the sensor’s fluorescence after detection of fluoride anions. Absorption and emission spectra further demonstrated that the designed sensor is a near-infrared chemosensor. The largest binding energy between NIR-BODIPY-Si and F− suggests that the sensor has an excellent selectivity to F− and the low barrier of the desilylation reaction accounts for the sensor’s rapid response speed to F−. We also provided the synthetic routine for the molecule sensor, with the expectation that this molecular design can shed some light on the experimentally based design procedure.

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The research leading to these results received funding from the National Natural Science Foundation of China under Grant Agreement No. 10874096 and the Shandong Provincial Natural Science Foundation, China, under the Grant Agreement No. ZR2014AM025.

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  1. Institute of Molecular Sciences and Engineering, Shandong University, Qingdao, 266235, People’s Republic of China

    Xiaochen Wang & Tianxin Bai

  2. School of Physics, Qingdao University, Qingdao, 266071, People’s Republic of China

    Tianshu Chu

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  1. Xiaochen Wang
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Xiaochen Wang: Conceptualization, Methodology, Writing—Original draft preparation. Tianxin Bai: Conceptualization, Methodology, Software, Visualization, Validation. Tianshu Chu: Conceptualization, Supervision, Funding acquisition, Writing—Reviewing and Editing.

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Wang, X., Bai, T. & Chu, T. A molecular design for a turn-off NIR fluoride chemosensor. J Mol Model 27, 104 (2021). https://doi.org/10.1007/s00894-021-04716-1

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