Deciphering the Structure-Property Relations in Substituted Heptamethine Cyanines

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Publikace nespadá pod Pedagogickou fakultu, ale pod Přírodovědeckou fakultu. Oficiální stránka publikace je na webu muni.cz.
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ŠTACKOVÁ Lenka MUCHOVA Eva RUSSO Marina SLAVÍČEK Petr ŠTACKO Peter KLÁN Petr

Rok publikování 2020
Druh Článek v odborném periodiku
Časopis / Zdroj Journal of Organic Chemistry
Fakulta / Pracoviště MU

Přírodovědecká fakulta

Citace
www https://pubs.acs.org/doi/10.1021/acs.joc.0c01104
Doi http://dx.doi.org/10.1021/acs.joc.0c01104
Klíčová slova Dyes and pigments; Reaction products; Absorption; Substituents; Electrical energy
Popis Heptamethine cyanines (Cy7) are fluorophores essential for modern bioimaging techniques and chemistry. Here, we systematically evaluated the photochemical and photophysical properties of a library of Cy7 derivatives containing diverse substituents in different positions of the heptamethine chain. A single substitution allows modulation of their absorption maxima in the range of 693-805 nm and photophysical properties, such as quantum yields of singlet-oxygen formation, decomposition, and fluorescence or affinity to singlet oxygen, within 2-3 orders of magnitude. The same substituent in different positions of the chain often exhibits distinctly contradictory effects, demonstrating that both the type and position of the substituent are pivotal for the design of Cy7-based applications. The combination of experimental results with quantum-chemical calculations provides insights into the structure-property relationship, the elucidation of which will accelerate the development of cyanines with properties tailored for specific applications, such as fluorescent probes and sensors, photouncaging, photodynamic therapy, or singlet-oxygen detection.
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