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@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 = {http://dx.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://dx.doi.org/10.1021/acs.joc.0c01104.
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