Explorations into the Effect of meso-Substituents in Tricarbocyanine Dyes: A Path to Diverse Biomolecular Probes and Materials

Rüdiger M. Exner, Fernando Cortezon-Tamarit, Sofia I. Pascu

Research output: Contribution to journalReview articlepeer-review

41 Citations (SciVal)

Abstract

Polymethine cyanine dyes have been widely recognized as promising chemical tools for a range of life science and biomedical applications, such as fluorescent staining of DNA and proteins in gel electrophoresis, fluorescence guided surgery, or as ratiometric probes for probing biochemical pathways. The photophysical properties of such dyes can be tuned through the synthetic modification of the conjugated backbone, for example, by altering aromatic cores or by varying the length of the conjugated polymethine chain. Alternative routes to shaping the absorption, emission, and photostability of dyes of this family are centered around the chemical modifications on the polymethine chain. This Minireview aims to discuss strategies for the introduction of substituents in the meso-position, their effect on the photophysical properties of these dyes and some structure–activity correlations which could help overcome common limitations in the state of the art in the synthesis.

Original languageEnglish
Pages (from-to)6230–6241
Number of pages12
JournalAngewandte Chemie - International Edition
Volume60
Issue number12
Early online date22 Sept 2020
DOIs
Publication statusPublished - 15 Mar 2021

Bibliographical note

Funding Information:
The authors thank the ERC for funding through the Consolidator Grant O2Sense (617107) and the ERC PoC Tools‐To‐Sense (963937), the EPSRC for funding through the CDT and CSCT (EO/L016354/1), and the University of Bath for the URSA‐Science Strategic PhD studentship. We also thank Prof. Paul Raithby for invaluable discussions and training in CSD CCDC searches.

Publisher Copyright:
© 2020 The Authors. Published by Wiley-VCH GmbH

Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.

Keywords

  • chemical probes
  • cyanine
  • fluorescence
  • imaging agent
  • meso-substitution

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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