Deciphering the Structure-Property Relations in Substituted
Heptamethine Cyanines

J 2020

Deciphering the Structure-Property Relations in Substituted Heptamethine Cyanines

ŠTACKOVÁ, Lenka; Eva MUCHOVA; Marina RUSSO; Petr SLAVÍČEK; Peter ŠTACKO et al.

Základní údaje

Originální název

Deciphering the Structure-Property Relations in Substituted Heptamethine Cyanines

Autoři

ŠTACKOVÁ, Lenka; Eva MUCHOVA; Marina RUSSO; Petr SLAVÍČEK; Peter ŠTACKO a Petr KLÁN

Vydání

Journal of Organic Chemistry, Washington, D.C. American Chemical Society, 2020, 0022-3263

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 4.354

Označené pro přenos do RIV

Ano

Kód RIV

RIV/00216224:14310/20:00114564

Organizační jednotka

Přírodovědecká fakulta

Klíčová slova anglicky

Dyes and pigments; Reaction products; Absorption; Substituents; Electrical energy

Štítky

H24, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 2. 6. 2025 10:36, Mgr. Michaela Hylsová, Ph.D.

Anotace

V originále

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.

Návaznosti

EF17_043/0009632, projekt VaV

Název: CETOCOEN Excellence

GA18-12477S, projekt VaV

Název: Fotoaktivace CO a H2S jako plynných signálních molekul pro biologické a medicinální aplikace

Investor: Grantová agentura ČR, Fotoaktivace CO a H2S jako plynných signálních molekul pro biologické a medicinální aplikace

6SA17811, interní kód MU

Název: Visible light-activated photocaged molecules for biological applications (Akronym: VLAMBA)

Investor: Jihomoravský kraj, Visible light-activated photocaged molecules for biological applications, Reintegrační granty

857560, interní kód MU
(Kód CEP: EF17_043/0009632)

Název: CETOCOEN Excellence (Akronym: CETOCOEN Excellence)

Investor: Evropská unie, CETOCOEN Excellence, Spreading excellence and widening participation

90121, velká výzkumná infrastruktura

Název: RECETOX RI

Citovat

ŠTACKOVÁ, Lenka; Eva MUCHOVA; Marina RUSSO; Petr SLAVÍČEK; Peter ŠTACKO a Petr KLÁN. Deciphering the Structure-Property Relations in Substituted Heptamethine Cyanines. Journal of Organic Chemistry. Washington, D.C.: American Chemical Society, 2020, roč. 85, č. 15, s. 9776-9790. ISSN 0022-3263. Dostupné z: https://doi.org/10.1021/acs.joc.0c01104.

@article{1707838,
   author = {Štacková, Lenka and Muchova, Eva and Russo, Marina and Slavíček, Petr and Štacko, Peter and Klán, Petr},
   article_location = {Washington, D.C.},
   article_number = {15},
   doi = {https://doi.org/10.1021/acs.joc.0c01104},
   keywords = {Dyes and pigments; Reaction products; Absorption; Substituents; Electrical energy},
   language = {eng},
   issn = {0022-3263},
   journal = {Journal of Organic Chemistry},
   title = {Deciphering the Structure-Property Relations in Substituted Heptamethine Cyanines},
   url = {https://pubs.acs.org/doi/10.1021/acs.joc.0c01104},
   volume = {85},
   year = {2020}
}

TY  - JOUR
ID  - 1707838
AU  - Štacková, Lenka - Muchova, Eva - Russo, Marina - Slavíček, Petr - Štacko, Peter - Klán, Petr
PY  - 2020
TI  - Deciphering the Structure-Property Relations in Substituted Heptamethine Cyanines
JF  - Journal of Organic Chemistry
VL  - 85
IS  - 15
SP  - 9776-9790
EP  - 9776-9790
PB  - American Chemical Society
SN  - 00223263
KW  - Dyes and pigments
KW  - Reaction products
KW  - Absorption
KW  - Substituents
KW  - Electrical energy
UR  - https://pubs.acs.org/doi/10.1021/acs.joc.0c01104
L2  - https://pubs.acs.org/doi/10.1021/acs.joc.0c01104
N2  - 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.
ER  -

ŠTACKOVÁ, Lenka; Eva MUCHOVA; Marina RUSSO; Petr SLAVÍČEK; Peter ŠTACKO a Petr KLÁN. Deciphering the Structure-Property Relations in Substituted Heptamethine Cyanines. \textit{Journal of Organic Chemistry}. Washington, D.C.: American Chemical Society, 2020, roč.~85, č.~15, s.~9776-9790. ISSN~0022-3263. Dostupné z: https://doi.org/10.1021/acs.joc.0c01104.

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