Synthesis of aminyl biradicals by base-induced Csp<sup>3</sup>–Csp<sup>3</sup> coupling of cationic azo dyes

Liu, Yizhu; Varava, Paul; Fabrizio, Alberto; Eymann, Léonard Y. M.; Tskhovrebov, Alexander G.; Planes, Ophélie Marie; Solari, Euro; Fadaei‐Tirani, Farzaneh; Scopelliti, Rosario; Sienkiewicz, Andrzej; Corminbœuf, Clémence; Severin, Kay

doi:10.1039/c9sc01502g

Cited by 30 publications

(19 citation statements)

References 61 publications

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“…Crystallographic parameters and refinement details for all complexes are listed in Table S1 . Overall, metrical parameters for triarylazoimidazoles in 5, 7 – 10 are similar to those reported for structurally relevant azocompounds [ 17 , 18 , 19 , 23 , 35 , 36 ] and imidazole derivatives [ 37 , 38 ]. CCDC 2058877-2058881 contain the supplementary crystallographic data for this paper.…”

Section: Methodssupporting

confidence: 76%

“…In this context, azoimidazoles are attractive chelating ligands with easily tunable electronic and photophysical properties via facile structural modifications [ 12 , 13 , 14 , 15 , 16 , 17 ]. Recently, we described a novel method for the synthesis of this important class of dyes, which employs nitrous oxide as a donor of azo group [ 17 , 18 , 19 ].…”

Section: Introductionmentioning

confidence: 99%

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Unprecedented Coordination-Induced Bright Red Emission from Group 12 Metal-Bound Triarylazoimidazoles

et al. 2021

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Arylazoimidazoles are important dyes which were intensively studied in the past. In contrast, triarylazoimidazoles (derivatives which carry aryl substituents at the imidazole core) received almost no attention in the scientific literature. Here, we report a new family of simple and easily accessible triarylazoimidazole-group 12 metal complexes, which feature highly efficient photo-luminescence emission (Φ up to 0.44). Novel compounds exhibit bright red emission in solution, which could be excited with a visible light.

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Section: Methodssupporting

confidence: 76%

Section: Introductionmentioning

confidence: 99%

Unprecedented Coordination-Induced Bright Red Emission from Group 12 Metal-Bound Triarylazoimidazoles

et al. 2021

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“…1. Overall, bond dimensions within the molecule are similar to those reported for structurally relevant azo compounds (Tskhovrebov et al, 2014(Tskhovrebov et al, , 2015Liu et al, 2019;Eymann et al, 2016;Nenajdenko et al, 2020). The molecule adopts a trans configuration with respect to the azo double bond.…”

Section: Structural Commentarysupporting

confidence: 69%

“…Azoimidazoles are a class of dyes that have found widespread applications in industry, as well as in laboratory research (Eymann et al, 2016;Tskhovrebov et al, 2014;Liu et al, 2019). They are widely used for dyeing natural and synthetic fibers.…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure of 2-[(E)-2-(4-bromophenyl)diazen-1-yl]-4,5-bis(4-methoxyphenyl)-1H-imidazole: the first example of a structurally characterized triarylazoimidazole

et al. 2021

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The title compound, C23H19BrN4O2, is a product of an azo coupling reaction between 3,4-bis(4-methoxyphenyl)imidazole and 4-bromophenyldiazonium tetrafluoroborate. Its crystal structure was determined using data collected at 120 K. The molecule adopts a trans configuration with respect to the N=N double bond. The imidazole and aryl rings attached to the azo linkage are coplanar within 12.73 (14)°, which indicates significant electron delocalization within the molecule. In the crystal, the molecules form centrosymmetric dimers via pairs of N—H...O hydrogen bonds.

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“…[ 4–6 ] So, codelivery of gene and drug in one system for synergistic cancer therapy that combine chemotherapy and gene therapy to ablate tumor is a promising strategy. [ 7–9 ] For this purpose, finding an efficient co‐carrier is necessary. [ 10–12 ]…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Copolymers Polyethyleneimine‐co‐Polyphenylalanine as Gene and Drug Codelivery Carrier

Liu

Guo

Feng

et al. 2021

Macromolecular Bioscience

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In this study, a series of hyperbranched copolymers polyethyleneimine‐co‐polyphenylalanine (PEI‐co‐PPhe) are synthesized by ring‐opening polymerization with phenylalanine‐N‐carboxyanhydride as monomer and PEI‐25k as initiator, using as a gene and drug codelivery carrier. Among them, PEI‐co‐PPhe (1:170) is selected out from transfection efficiency and cytotoxicity tests. Then, doxorubicin‐cis‐aconitic anhydride (CAD) and BCl2‐shRNA (as a therapeutic gene) are coloaded into the PEI‐co‐PPhe carrier to form PEI‐co‐PPhe/Bcl2‐shRNA/CAD complexes as a codeliver system. When the mass ratio of PEI‐co‐PPhe:Bcl2‐shRNA:CAD is 5:1:1, the codeliver system has the most obvious synergistic therapeutic effect against B16F10 cells. Confirmed by confocal laser scanning microscope and flow cytometry, compared with drug and gene alone, the codeliver complexes can be endocytosed into B16F10 cells efficiently. As a result, the appropriate length of PPhe grafted on PEI will improve the gene transfer efficiency and decrease cytotoxicity, as well as effective codelivery of gene and drug into cancer cells to be a promising codelivery carrier for cancer therapy.

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Synthesis of aminyl biradicals by base-induced Csp³–Csp³ coupling of cationic azo dyes

Abstract: Deprotonation of cationic azo dyes results in the formation of aminyl biradicals.

Cited by 30 publications

References 61 publications

Unprecedented Coordination-Induced Bright Red Emission from Group 12 Metal-Bound Triarylazoimidazoles

Unprecedented Coordination-Induced Bright Red Emission from Group 12 Metal-Bound Triarylazoimidazoles

Crystal structure of 2-[(E)-2-(4-bromophenyl)diazen-1-yl]-4,5-bis(4-methoxyphenyl)-1H-imidazole: the first example of a structurally characterized triarylazoimidazole

Synthesis of Copolymers Polyethyleneimine‐co‐Polyphenylalanine as Gene and Drug Codelivery Carrier

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Synthesis of aminyl biradicals by base-induced Csp3–Csp3 coupling of cationic azo dyes

Abstract: Deprotonation of cationic azo dyes results in the formation of aminyl biradicals.

Cited by 30 publications

References 61 publications

Unprecedented Coordination-Induced Bright Red Emission from Group 12 Metal-Bound Triarylazoimidazoles

Unprecedented Coordination-Induced Bright Red Emission from Group 12 Metal-Bound Triarylazoimidazoles

Crystal structure of 2-[(E)-2-(4-bromophenyl)diazen-1-yl]-4,5-bis(4-methoxyphenyl)-1H-imidazole: the first example of a structurally characterized triarylazoimidazole

Synthesis of Copolymers Polyethyleneimine‐co‐Polyphenylalanine as Gene and Drug Codelivery Carrier

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Synthesis of aminyl biradicals by base-induced Csp³–Csp³ coupling of cationic azo dyes