Azo-tagged C4N4 fluorophores: unusual overcrowded structures and their application to fluorescent imaging

Kohei, Miki; Takizawa, Naoki; Tsutsumi, Ryosuke; Xu, Wei; Kumagai, Naoya

doi:10.1039/d3ob00049d

Cited by 2 publications

(1 citation statement)

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“…Azo compounds usually refer to compounds containing -N=N- double bond, which can be divided into aryl azo compounds and alkyl azo compounds depending on the substituents on the -N=N- double bonds, as well as symmetrical and asymmetrical azo compounds from the point of view of structure. Azo compounds date back to 1859, and the high reactivity of -N=N- double bonds endow azo compounds with wide applications in many fields such as organic dyes, radical reaction initiators, and so on [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 ]. On the other hand, azo compounds have cis and trans isomers, which can convert to each other under light irradiation or heating, as was discovered as early as 1937.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in the Synthesis of Aromatic Azo Compounds

Zhao,

Tang,

Han

2023

Molecules

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Aromatic azo compounds have -N=N- double bonds as well as a larger π electron conjugation system, which endows aromatic azo compounds with wide applications in the fields of functional materials. The properties of aromatic azo compounds are closely related to the substituents on their aromatic rings. However, traditional synthesis methods, such as the coupling of diazo salts, have a significant limitation with respect to the structural design of aromatic azo compounds. Therefore, many scientists have devoted their efforts to developing new synthetic methods. Moreover, recent advances in the synthesis of aromatic azo compounds have led to improvements in the design and preparation of light-response materials at the molecular level. This review summarizes the important synthetic progress of aromatic azo compounds in recent years, with an emphasis on the pioneering contribution of functional nanomaterials to the field.

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Section: Introductionmentioning

confidence: 99%

Recent Advances in the Synthesis of Aromatic Azo Compounds

Zhao,

Tang,

Han

2023

Molecules

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Photoswitching Characteristics, Photochromism and Mechanochromism of Extended π‐Conjugated Azopyrazole and Azoisoxazole Derivatives

Kumar,

Nasare,

Parthiban

et al. 2024

ChemPhotoChem

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Herein, we report extended π‐conjugated arylazopyrazoles and arylazoisoxazoles towards tuning and modulation of their intrinsic properties. In this regard, we systematically introduced phenyl, styryl, (triphenylvinyl)styryl, phenylethynyl groups at ortho, meta, and para positions relative to the azo unit to extend the π‐conjugation and vary the electronic coupling. In addition, the heterocyclic substituents were also modified. Overall, 20 photoswitches with modular substituents have been synthesized and studied for the photoswitching ability and thermal relaxations of Z isomers in the solution phase and solid state. Besides deciphering the importance of extending conjugation in photoswitching characteristics, intriguing properties such as mechanochromism and reversible bidirectional photochromism in the solid state were also unravelled. Through systematic studies, we envisage the effect of electronic coupling due to π‐conjugation and its impact on longer wavelength light‐induced photoswitching that holds several application potentials.

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Azo-tagged C4N4 fluorophores: unusual overcrowded structures and their application to fluorescent imaging

Abstract: The C4N4 fluorophore is an intense fluorescence emitter featuring a 2,5-diaminopyrimidine core comprising four carbon and four nitrogen atoms. A series of C4N4 derivatives was photochemically dimerized at the 5-amino...

Cited by 2 publications

References 39 publications

Recent Advances in the Synthesis of Aromatic Azo Compounds

Recent Advances in the Synthesis of Aromatic Azo Compounds

Photoswitching Characteristics, Photochromism and Mechanochromism of Extended π‐Conjugated Azopyrazole and Azoisoxazole Derivatives

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