Synthesis and Spectral Properties of 6'-Triazolyl-Dihydroxanthene-Hemicyanine Fused Near-Infrared Dyes

06 April 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

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 dual aim of providing molecular diversity and fine tuning spectral properties of these near-infrared (NIR)-active materials. This was implemented by reacting 16 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 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.

Keywords

click chemistry
Dihydroxanthene-Hemicyanine Fused Near-Infrared Fluorophores
fluorescence
NIR dyes
triazole
molecular diversity

Supplementary materials

Title
Description
Actions
Title
Triazole-based-DHX-hemicyanine-fused-dyes-ChemRxiv-SI
Description
Actions

Comments

Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.