Versatile transamination in quinonediimine chemistry: Towards a novel class of water soluble UV/violet chromophores

Chen, Zhongrui; Bert, Maxime; Pascal, Simon; Canard, Gabriel; Siri, Olivier

doi:10.1016/j.tetlet.2019.151024

Cited by 4 publications

(3 citation statements)

References 24 publications

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“…Protonated forms 9 and 10 are nonemissive featuring a quenching of the fluorescence upon protonation of 8b . In the presence of DBU (up to 4 equiv), the complete disappearance of 8b is monitored in favor of the formation of neutral quinoidal form 11 , exhibiting absorption in the blue region, at 483 nm, a common signature of 2,5-diamino-benzoquinonediimine derivatives. − Moreover, the fluorescence of 11 is blue-shifted to 550 nm and significantly quenched, with a quantum yield of 0.08 (Figure S23). Eventually, it is worth mentioning that 8b features good photostability, its maximum fluorescence intensity being only slightly deteriorated upon prolonged visible light irradiation (see Figure S24).…”

Section: Resultsmentioning

confidence: 99%

Modified Indulines: From Dyestuffs to In Vivo Theranostic Agents

Chen

Pascal

Daurat³

et al. 2021

ACS Appl. Mater. Interfaces

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The efficient, versatile and straightforward synthesis of the first N-alkyl analogs of induline 3B (8a and 8b) is reported. Thanks to the introduction of lipophilic substituents and its attractive photophysical properties (far-red emission and production of singlet oxygen), phenazinium 8b can be used as theranostic agent and shows, at very low concentration (100 nM), a remarkable ability to: i) image cells and zebrafish embryos with high quality under both mono (514 nm) and biphotonic (790 and 810 nm) excitations, ii) efficiently and quickly penetrate cancer cells rather than healthy fibroblast, iii) induce a total or almost total cancer cell death in vitro and in vivo after illumination (exc = 540-560 nm). The molecular structure of 8b is based on a triamino-phenazinium core only, with no need for additional components, highlighting the emergence of a minimalistic and versatile class of fluorescent probes for targeted photodynamic cancer therapy.

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Section: Resultsmentioning

confidence: 99%

Modified Indulines: From Dyestuffs to In Vivo Theranostic Agents

Chen

Pascal

Daurat³

et al. 2021

ACS Appl. Mater. Interfaces

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“…Nietzki (1847–1917) is an unfamiliar figure to many modern organic chemists, but he made farsighted contributions in areas of enduring importance. − Nietzki’s impact can be measured by the frequency with which compounds first made in his research group are used today. In particular, BTA ( 1 ) and its derivatives are at the center of an imposing array of projects, including studies in which the compounds are used as precursors of redox-active materials, − ligands in coordination chemistry, − components for making metal–organic frameworks (MOFs) and covalent organic frameworks (COFs) by modular construction, − monomers for producing polymers, − components of switches and sensors, , precursors for synthesizing diverse heterocyclic compounds, − and enzyme inhibitors for use in treating cancer …”

Section: Introductionmentioning

confidence: 99%

Refreshing the Legacy of Rudolf Nietzki: Benzene-1,2,4,5-tetramine and Related Compounds

Sosoe,

Malveau,

Maris

et al. 2023

J. Org. Chem.

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Like hydroquinones and quinones, aromatic compounds with multiple NH2 groups and the corresponding quinonediimines have the potential to serve as components of useful redox-active organic materials. Benzene-1,2,4,5-tetramine (BTA) and its oxidized form BTA-H2 offer a promising redox pair of this type, and the compounds have proven to be useful in many areas of chemistry. However, key aspects of their behavior have remained poorly studied, such as the nature of their protonated forms, their preferred molecular structures, their reactivity, and their organization in condensed phases. In the present work, we have used a combination of improved methods of synthesis, computation, spectroscopic studies, and structural analyses to develop a deeper understanding of BTA, BTA-H2, their salts, and related compounds. The new knowledge is expected to accelerate exploitation of the compounds in areas of materials science where desirable properties can only be attained by properly controlling the organization of molecular components.

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“…Selecting 1,2,4,5-BTA ( 1 ) for detailed study is warranted because the compound is at the center of an impressive range of projects in which it is used as a precursor of redox-active materials, − a ligand in coordination chemistry, − a component of metal–organic frameworks (MOFs) and covalent organic frameworks (COFs), − a monomer for producing polymers, − a component of switches and sensors, , a precursor for synthesizing diverse heterocyclic compounds, − and an enzyme inhibitor for use in treating cancer . However, fuller exploitation of 1,2,4,5-BTA ( 1 ) and analogues such as 1,2,3,4-BTA ( 3 ) will require a better understanding of their fundamental properties, such as the nature of their salts and their preferred patterns of association in the solid state, which will determine how they are best used as the components of redox-active materials.…”

Section: Introductionmentioning

confidence: 99%

Strongly Hydrogen-Bonded Networks Formed by Sulfate and Bisulfate Salts of Benzenetetramines

Sosoe,

Maris,

Wuest

2023

Crystal Growth & Design

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Benzenetetramines, like other aromatic compounds with multiple NH2 groups, are easily oxidized and are attractive candidates for use as components of redox-active organic materials. However, many aspects of the chemistry of benzenetetramines and related compounds remain poorly understood, such as the nature of their salts and their preferred patterns of association, which determine how they can be used to construct predictably ordered redox-active solids. To provide relevant new information, we have studied a series of sulfate and bisulfate salts of the 1,2,4,5- and 1,2,3,4-isomers, which have been found to crystallize as strongly hydrogen-bonded networks. The results of this work promise to facilitate the use of benzenetetramines and other complex arylamines as components of redox-active organic solids.

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Versatile transamination in quinonediimine chemistry: Towards a novel class of water soluble UV/violet chromophores

Cited by 4 publications

References 24 publications

Modified Indulines: From Dyestuffs to In Vivo Theranostic Agents

Modified Indulines: From Dyestuffs to In Vivo Theranostic Agents

Refreshing the Legacy of Rudolf Nietzki: Benzene-1,2,4,5-tetramine and Related Compounds

Strongly Hydrogen-Bonded Networks Formed by Sulfate and Bisulfate Salts of Benzenetetramines

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