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Issue 39, 2019
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Far-red/near-infrared emitting, two-photon absorbing, and bio-stable amino-Si-pyronin dyes

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Abstract

Organic fluorophores emitting in the far-red/near-infrared (NIR) wavelength region are in great demand for minimal autofluorescence and reduced light scattering in deep tissue or whole body imaging. Currently, only a few classes of far-red/NIR fluorophores are available including widely used cyanine dyes, which are susceptible to photobleaching and form nonfluorescent aggregates. Even rare are those far-red/NIR emitting dyes that have two-photon imaging capability. Here we report a new class of far-red/NIR-emitting dyes that are photo-stable, very bright, biocompatible, and also two-photon absorbing. The introduction of an electron-withdrawing group such as N-acyl or N-alkoxycarbonyl groups on the C-10-amino substituent of the new julolidine-derived amino-Si-pyronin dyes (ASiPj), which emit in the far-red region, causes large bathochromic shifts, leading to NIR-emitting amino-Si-pyronin dyes (NIR-ASiPj) having high cellular stability. Furthermore, the ASiPj–NIR-ASiPj couple offers a novel ratiometric bioimaging platform with a large spectral gap, as demonstrated here with a boronate-containing NIR-ASiPj derivative that is converted to the corresponding ASiPj dye upon reaction with hydrogen peroxide.

Graphical abstract: Far-red/near-infrared emitting, two-photon absorbing, and bio-stable amino-Si-pyronin dyes

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Supplementary files

Article information


Submitted
10 May 2019
Accepted
03 Aug 2019
First published
06 Aug 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 9028-9037
Article type
Edge Article

Far-red/near-infrared emitting, two-photon absorbing, and bio-stable amino-Si-pyronin dyes

K. H. Kim, S. Singha, Y. W. Jun, Y. J. Reo, H. R. Kim, H. G. Ryu, S. Bhunia and K. H. Ahn, Chem. Sci., 2019, 10, 9028
DOI: 10.1039/C9SC02287B

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