Near‐Infrared Fluorophores Based on Heptamethine Cyanine Dyes: From Their Synthesis and Photophysical Properties to Recent Optical Sensing and Bioimaging Applications

Medeiros, Natália G.; Braga, Cláudia A.; Câmara, Viktor S.; Duarte, Rodrigo C.; Rodembusch, Fabiano S.

doi:10.1002/ajoc.202200095

Cited by 37Molecular Sensors and Ion DetectionLuminescence and Fluorescent MaterialsPhotochemistry and Electron Transfer Studies

Near‐Infrared Fluorophores Based on Heptamethine Cyanine Dyes: From Their Synthesis and Photophysical Properties to Recent Optical Sensing and Bioimaging Applications

Medeiros, Natália G., Braga, Cláudia A., Câmara, Viktor S., Duarte, Rodrigo C., Rodembusch, Fabiano S.·2022·Asian Journal of Organic Chemistry

DOI 10.1002/ajoc.202200095

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Abstract

This review summarizes diverse synthetic methodologies to prepare a wide range of heptamethine cyanine dyes, including symmetrical, unsymmetrical, and meso‐substituted derivatives, and their photophysical properties and uses. Their sensing applications are also discussed, considering the nature of their electronic structures and photophysical properties. The optical sensing applications of these compounds can be potentially expanded via structural modification, broadening their absorption amplitude and spectral emission range from the ultraviolet to near‐infrared (NIR) region. In this review, several recent practical applications of the heptamethine cyanine dyes for ion and small molecule sensing, as well as bioimaging, are covered and discussed.

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Significant red-shifts in emission wavelength are primarily achieved through elongation of the polymethine chain and fine structural modifications, including extension or modification of terminal heterocycles, electron-donating or withdrawing substituents on terminal units, and cyclization of the polymethine chain.
“Significant red-shifts in emission wavelength are primarily achieved through two strategies: elongation of the polymethine chain and fine structural modifications, including extension or modification of terminal heterocycles, electron-donating or withdrawing substituents on terminal units and cyclization of the polymethine chain111–113.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [113]
Each methylene unit inserted between donor and acceptor typically induces a red-shift of ~100 nm.
“A general rule, as exemplified in cyanine dyes, is that each methylene unit inserted between donor and acceptor typically induces a red-shift of ~100 nm111–123.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [113]

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Near-infrared heptamethine cyanine dyes. Synthesis, spectroscopic characterization, thermal properties and photostability
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Fluorogenic polymethine dyes by intramolecular cyclization
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An anthracene-based molecular rotor as a theranostic agent for viscosity sensing and imaging-guided photodynamic therapy
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A General Strategy To Access Fluorogenic Heptamethine Cyanines through Polymethine Reactivity
Kumarasiri, B. D., Jeevaratnam, K., Wherritt, D., & Usama, S. M. (2026) · Organic Letters · doi:10.1021/acs.orglett.6c01286
Ethoxy Meso-Modified Heptamethine Cyanine Fluorophores: Synthesis, Photophysical Properties and BSA Sensing Study
Ahmed, T. E., & Henary, M. (2026) · Molecules · doi:10.3390/molecules31132267

Authors: Medeiros, N. G., Braga, C. A., Câmara, V. S., Duarte, R. C., & Rodembusch, F. S.
Affiliations: Universidade Federal do Rio Grande do Sul (BR)
Grupo de Pesquisa em Fotoquímica Orgânica Aplicada (GPFOA) Instituto de Química Universidade Federal do Rio Grande do Sul Av. Bento Gonçalves 9500 CEP 91501-970 Porto Alegre-RS Brazil
Corresponding author: Rodembusch, Fabiano S.
ORCID: Medeiros, Natália G.
Braga, Cláudia A.
Câmara, Viktor S.
Duarte, Rodrigo C.
Rodembusch, Fabiano S.
Venue: Asian Journal of Organic Chemistry
Publisher: Wiley
Published: 2022-04-26
Volume: 11
Issue: 6
ISSN: 2193-5807 (ISSN-L)
2193-5815
DOI: 10.1002/ajoc.202200095
OpenAlex: W4221037631
Cited by: 36
References: 139
Citations by year: 2026: 4 · 2025: 9 · 2024: 13 · 2023: 9 · 2022: 1
FWCI: 2.89
Type: journal article
Language: en
Open access: closed
Licence: onlinelibrary.wiley.com/termsAndConditions#vor (vor)
Locations: Asian Journal of Organic Chemistry (publishedVersion)
Funders: Conselho Nacional de Desenvolvimento Científico e Tecnológico (409855/2018-9, 305954/2019-9)
Topics: Physical Sciences › Chemistry › Spectroscopy › Molecular Sensors and Ion Detection
Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
Physical Sciences › Chemistry › Physical and Theoretical Chemistry › Photochemistry and Electron Transfer Studies
Keywords: heptamethine cyanine dyes, near-infrared fluorophores, dye synthesis, photophysical properties, optical sensing, ion detection, small molecule detection, bioimaging, electronic structure

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Near‐Infrared Fluorophores Based on Heptamethine Cyanine Dyes: From Their Synthesis and Photophysical Properties to Recent Optical Sensing and Bioimaging Applications

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