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Synthesis and spectral properties of 6′-triazolyl-dihydroxanthene-hemicyanine fused near-infrared dyes

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Abstract

We describe the synthesis of a range of 6′-triazolyl-dihydroxanthene-hemicyanine (DHX-hemicyanine) fused dyes through an effective copper-catalyzed azide–alkyne cycloaddition (CuAAC) “click” reaction, with the aim of providing molecular diversity and evaluating the spectral properties of these near-infrared (NIR)-active materials. This was implemented by reacting 15 different aliphatic and aromatic azides with a terminal alkynyl-based DHX-hemicyanine hybrid scaffold prepared in four steps and 35% overall yield from 4-bromosalicylaldehyde. The resulting triazole derivatives have been fully characterized and their optical properties determined both in organic solvents and under simulated physiological conditions (phosphate buffered saline containing 5% of bovine serum albumin protein). This systematic study is a first important step towards the development of NIR-I fluorogenic “click-on” dyes or related photoactive agents for light-based diagnostic and/or therapeutic applications.

Graphical abstract: Synthesis and spectral properties of 6′-triazolyl-dihydroxanthene-hemicyanine fused near-infrared dyes

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Supplementary files

Article information


Submitted
07 Apr 2020
Accepted
24 Jun 2020
First published
25 Jun 2020

New J. Chem., 2020, Advance Article
Article type
Paper

Synthesis and spectral properties of 6′-triazolyl-dihydroxanthene-hemicyanine fused near-infrared dyes

L. Gu, K. Renault, A. Romieu, J. Richard and R. Srinivasan, New J. Chem., 2020, Advance Article , DOI: 10.1039/D0NJ01724H

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