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Synthesis and photophysical activity of 6-substituted isocoumarins

Elena Sergeevna Fedina 1, 2
Elena Sergeevna Fedina
,  , 
Kseniya Leonidovna Isakovskaya 1
Kseniya Leonidovna Isakovskaya
, 
Dmitry Victorovich Muratov 1
Dmitry Victorovich Muratov
, 
Dmitry Alexandrovich Loginov 1, 3
Dmitry Alexandrovich Loginov
1 A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russian Federation
2 Sirius University of Science and Technology, Sochi, Russian Federation
3 G.V. Plekhanov Russian University of Economics, Moscow, Russian Federation
10.1016/j.mencom.2024.01.032
Published 2023-12-25
Communication , Volume 34, Issue 1, 107-109
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Fedina E. S. et al. Synthesis and photophysical activity of 6-substituted isocoumarins // Mendeleev Communications. 2023. Vol. 34. No. 1. pp. 107-109.
GOST all authors (up to 50) Copy
Fedina E. S., Arsenov M. A., Isakovskaya K. L., Muratov D. V., Loginov D. A. Synthesis and photophysical activity of 6-substituted isocoumarins // Mendeleev Communications. 2023. Vol. 34. No. 1. pp. 107-109.
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TY - JOUR
DO - 10.1016/j.mencom.2024.01.032
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.01.032
TI - Synthesis and photophysical activity of 6-substituted isocoumarins
T2 - Mendeleev Communications
AU - Fedina, Elena Sergeevna
AU - Arsenov, Mikhail Anatol'evich
AU - Isakovskaya, Kseniya Leonidovna
AU - Muratov, Dmitry Victorovich
AU - Loginov, Dmitry Alexandrovich
PY - 2023
DA - 2023/12/25
PB - Mendeleev Communications
SP - 107-109
IS - 1
VL - 34
ER -
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@article{2023_Fedina,
author = {Elena Sergeevna Fedina and Mikhail Anatol'evich Arsenov and Kseniya Leonidovna Isakovskaya and Dmitry Victorovich Muratov and Dmitry Alexandrovich Loginov},
title = {Synthesis and photophysical activity of 6-substituted isocoumarins},
journal = {Mendeleev Communications},
year = {2023},
volume = {34},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.01.032},
number = {1},
pages = {107--109},
doi = {10.1016/j.mencom.2024.01.032}
}
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Fedina, Elena Sergeevna, et al. “Synthesis and photophysical activity of 6-substituted isocoumarins.” Mendeleev Communications, vol. 34, no. 1, Dec. 2023, pp. 107-109. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.01.032.
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Keywords

C–H annulation
cross-coupling
homogeneous catalysis.
isocoumarins
luminescence

Abstract

6-Substituted isocoumarins with aryl, alkynyl, and diphenyl-amino substituents were synthesized from 4-bromobenzoic acid by annulation with tolane via rhodium-catalyzed C-H activation followed by palladium-catalyzed cross-coupling reactions. The compounds obtained exhibit luminescence emission in the violet-blue region (370-480 nm) with quantum yields up to 95% (for the diphenylamino derivative). Aggregation of biphenyl-substituted isocoumarin leads to a strong bathochromic shift (by 80 nm) of emission as a result of intermolecular π-π stacking interactions.

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