Jump to main content
Jump to site search

Issue 20, 2019
Previous Article Next Article

Rhodols – synthesis, photophysical properties and applications as fluorescent probes

Author affiliations

Abstract

The formal replacement of one dialkylamino group in rhodamines with a hydroxyl group transforms them into rhodols. This apparently minor difference is not as small as one may think; rhodamines belong to the cyanine family whereas rhodols belong to merocyanines. Discovered in the late 19th century, rhodols have only very recently begun to gain momentum in the field of advanced fluorescence imaging. This is in part due to the increased understanding of their photophysical properties, and new methods of synthesis. Rationalization of how the nature and arrangement of polar substituents around the core affect the photophysical properties of rhodols is now possible. The emergence of so-called π-expanded and heteroatom-modified rhodols has also allowed their fluorescence to be bathochromically shifted into regions applicable for biological imaging. This review serves to outline applicable synthetic strategies for the synthesis of rhodols, and to highlight important structure–property relationships. In the first part of this Review, various synthetic methods leading to rhodols are presented, followed by structural considerations and an overview of photophysical properties. The second part of this review is entirely devoted to the applications of rhodols as fluorescent reporters in biological imaging.

Graphical abstract: Rhodols – synthesis, photophysical properties and applications as fluorescent probes

Back to tab navigation

Supplementary files

Publication details

The article was received on 28 Feb 2019 and first published on 24 Sep 2019


Article type: Review Article
DOI: 10.1039/C9CS00166B
Chem. Soc. Rev., 2019,48, 5242-5265

  •   Request permissions

    Rhodols – synthesis, photophysical properties and applications as fluorescent probes

    Y. M. Poronik, K. V. Vygranenko, D. Gryko and D. T. Gryko, Chem. Soc. Rev., 2019, 48, 5242
    DOI: 10.1039/C9CS00166B

Search articles by author

Spotlight

Advertisements