Conjugates of 8-[2,2’-bipyridinyl]coumarins as potential chemosensors for Al3+, Cu2+, Cd2+, Zn2+ ions: synthesis and photophysical properties

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Conjugates of 8-[2,2’-bipyridinyl]coumarins as potential chemosensors for Al3+, Cu2+, Cd2+, Zn2+ ions: synthesis and photophysical properties. / Sharapov, Ainur D.; Fatykhov, Ramil F.; Khalymbadzha, Igor A. et al.
In: Chimica Techno Acta, Vol. 10, No. 4, 202310417, 2023.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{181c58b1c9dd4f58aa495a054385f112,

title = "Conjugates of 8-[2,2{\textquoteright}-bipyridinyl]coumarins as potential chemosensors for Al3+, Cu2+, Cd2+, Zn2+ ions: synthesis and photophysical properties",

abstract = "In this work, we report the synthesis of novel coumarin-bipyridine conjugates using a sequence of C–C coupling reaction between 5,7-dimethox-ycoumarins and 3-pyridyl-6-aryl-1,2,4-triazines followed by the Boger reaction with norbornandiene to obtain 8-[2,2'-bipyridyl]-5,7-dimethox-ycoumarins. Photophysical properties were investigated for the obtained series of 8-[2,2'-bipyridyl]-5,7-dimethoxycoumarins: absorption and emission wavelength maxima are in the region of 212–296 and 401–410 nm, respectively; Stokes shifts are up to 116 nm, and fluorescence quantum yields are up to 15.0%. It was found that titrating the conjugates with Al3+, Zn2+, and Cd2+ ions results in an increase in the intensity of the emission maxima of the complexes, while the opposite effect was observed in the case of titration with Cu2+ ions. These findings suggest that the studied compounds may be considered as promising chemosensing materials. Finally, a positive solvatochromism of 8-[2,2'-bipyridyl]coumarins and their metal complexes was established. The experimental data are supported by mathematical calculations according to the Lippert-Mataga equation and Kosower diagram.",

author = "Sharapov, {Ainur D.} and Fatykhov, {Ramil F.} and Khalymbadzha, {Igor A.} and Kopchuk, {Dmitry S.} and Nikonov, {Igor L.} and Potapova, {Anastasiya P.} and Shtaitz, {Yaroslav k.} and Slepukhin, {Pavel A.}",

note = "The research funding from the Ministry of Science and Higher Education of the Russian Federation (Ural Federal University Program of Development within the Priority-2030 Program) is gratefully acknowledged.",

year = "2023",

doi = "10.15826/chimtech.2023.10.4.17",

language = "English",

volume = "10",

journal = "Chimica Techno Acta",

issn = "2409-5613",

publisher = "Издательство Уральского университета",

number = "4",

}

RIS

TY - JOUR

T1 - Conjugates of 8-[2,2’-bipyridinyl]coumarins as potential chemosensors for Al3+, Cu2+, Cd2+, Zn2+ ions: synthesis and photophysical properties

AU - Sharapov, Ainur D.

AU - Fatykhov, Ramil F.

AU - Khalymbadzha, Igor A.

AU - Kopchuk, Dmitry S.

AU - Nikonov, Igor L.

AU - Potapova, Anastasiya P.

AU - Shtaitz, Yaroslav k.

AU - Slepukhin, Pavel A.

N1 - The research funding from the Ministry of Science and Higher Education of the Russian Federation (Ural Federal University Program of Development within the Priority-2030 Program) is gratefully acknowledged.

PY - 2023

Y1 - 2023

N2 - In this work, we report the synthesis of novel coumarin-bipyridine conjugates using a sequence of C–C coupling reaction between 5,7-dimethox-ycoumarins and 3-pyridyl-6-aryl-1,2,4-triazines followed by the Boger reaction with norbornandiene to obtain 8-[2,2'-bipyridyl]-5,7-dimethox-ycoumarins. Photophysical properties were investigated for the obtained series of 8-[2,2'-bipyridyl]-5,7-dimethoxycoumarins: absorption and emission wavelength maxima are in the region of 212–296 and 401–410 nm, respectively; Stokes shifts are up to 116 nm, and fluorescence quantum yields are up to 15.0%. It was found that titrating the conjugates with Al3+, Zn2+, and Cd2+ ions results in an increase in the intensity of the emission maxima of the complexes, while the opposite effect was observed in the case of titration with Cu2+ ions. These findings suggest that the studied compounds may be considered as promising chemosensing materials. Finally, a positive solvatochromism of 8-[2,2'-bipyridyl]coumarins and their metal complexes was established. The experimental data are supported by mathematical calculations according to the Lippert-Mataga equation and Kosower diagram.

AB - In this work, we report the synthesis of novel coumarin-bipyridine conjugates using a sequence of C–C coupling reaction between 5,7-dimethox-ycoumarins and 3-pyridyl-6-aryl-1,2,4-triazines followed by the Boger reaction with norbornandiene to obtain 8-[2,2'-bipyridyl]-5,7-dimethox-ycoumarins. Photophysical properties were investigated for the obtained series of 8-[2,2'-bipyridyl]-5,7-dimethoxycoumarins: absorption and emission wavelength maxima are in the region of 212–296 and 401–410 nm, respectively; Stokes shifts are up to 116 nm, and fluorescence quantum yields are up to 15.0%. It was found that titrating the conjugates with Al3+, Zn2+, and Cd2+ ions results in an increase in the intensity of the emission maxima of the complexes, while the opposite effect was observed in the case of titration with Cu2+ ions. These findings suggest that the studied compounds may be considered as promising chemosensing materials. Finally, a positive solvatochromism of 8-[2,2'-bipyridyl]coumarins and their metal complexes was established. The experimental data are supported by mathematical calculations according to the Lippert-Mataga equation and Kosower diagram.

UR - http://www.scopus.com/inward/record.url?partnerID=8YFLogxK&scp=85181965606

UR - https://elibrary.ru/item.asp?id=60040560

U2 - 10.15826/chimtech.2023.10.4.17

DO - 10.15826/chimtech.2023.10.4.17

M3 - Article

VL - 10

JO - Chimica Techno Acta

JF - Chimica Techno Acta

SN - 2409-5613

IS - 4

M1 - 202310417

ER -

ID: 51601118