Issue 11, 2021

Red-to-NIR emissive radical cations derived from simple pyrroles

Abstract

Red-to-near-infrared (NIR) fluorophores are highly desirable in bio-imaging studies with advantages of high tissue penetration ability and less interference from auto-fluorescence. However, their preparation usually requires tedious synthetic procedures, which seriously restrict their applications. Thus, the direct preparation of red-to-NIR fluorophores from easily available substrates is highly desirable. Compared with the conventional closed-shell fluorophores, radical cations feature a large red-shift absorption, but only very few of them are fluorescent and they suffer from high instability. Herein, we proposed a convenient strategy for the preparation of red-to-NIR fluorophores through air oxidation of electron-rich 2,5-dimethylpyrroles to in situ generate red-to-NIR emissive radical cations, which can be stabilized by adsorption on silica gel-coated thin layer chromatography (TLC) plates or encapsulated in cucurbit[7]uril (CB[7]). The radical cations derived from pyrroles were verified using electron paramagnetic resonance (EPR) spectroscopy, theoretical calculations and one-electron oxidation experiments. Moreover, the pyrrole-derived radical cations encapsulated in CB[7] can be used for mitochondrial imaging in living cells with high specificity and in vivo imaging with long-term stability. The easily available pyrrole-derived radical cations with red-to-NIR emission are thus promising for biomedical applications.

Graphical abstract: Red-to-NIR emissive radical cations derived from simple pyrroles

Supplementary files

Article information

Article type
Communication
Submitted
15 Jul 2021
Accepted
01 Sep 2021
First published
01 Sep 2021

Mater. Horiz., 2021,8, 3082-3087

Red-to-NIR emissive radical cations derived from simple pyrroles

L. Zheng, W. Zhu, Z. Zhou, K. Liu, M. Gao and B. Z. Tang, Mater. Horiz., 2021, 8, 3082 DOI: 10.1039/D1MH01121A

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