Axially Chiral Stable Radicals: Resolution and Characterization of Blatter Radical Atropisomers

Bodzioch, Agnieszka; Pietrzak, Anna; Kaszyński, Piotr

doi:10.1021/acs.orglett.1c02733

Cited by 8 publications

(9 citation statements)

References 49 publications

(69 reference statements)

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“…13 [1,2,4]triazine (2k). 71 Following the general procedure, benzo[e] [1,2,4]triazine 2k (84.2 mg, 99% yield) was obtained from 92.3 mg (0.454 mmol) of N-oxide 5k as a yellow solid. The analytical data was identical to that reported previously.…”

Section: -(Morpholin-4-yl)benzo[e][124]triazine (2c)mentioning

confidence: 99%

3-Substituted Blatter Radicals: Cyclization of N-Arylguanidines and N-Arylamidines to Benzo[e][1,2,4]triazines and PhLi Addition

2023

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A series of 3-amino-and 3-alkyl-substituted 1-phenyl-1,4dihydrobenzo [e][1,2,4]triazin-4-yls was prepared in four steps involving Narylation, cyclization of N-arylguanidines and N-arylamidines, reduction of the resulting N-oxides to benzo[e][1,2,4]triazines, and subsequent addition of PhLi followed by aerial oxidation. The resulting seven C(3)-substituted benzo [e][1,2,4]triazin-4-yls were analyzed by spectroscopic and electrochemical methods augmented with density functional theory (DFT) methods. Electrochemical data were compared to DFT results and correlated with substituent parameters.

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Section: -(Morpholin-4-yl)benzo[e][124]triazine (2c)mentioning

confidence: 99%

3-Substituted Blatter Radicals: Cyclization of N-Arylguanidines and N-Arylamidines to Benzo[e][1,2,4]triazines and PhLi Addition

2023

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“…Reproduced with permission. [ 146 ] Copyright 2021, American Chemical Society. c) Main plot: single‐crystal conductivity, σ , of diradical 54 as a function of the reciprocal temperature (1000/ T ), with the fits in the high‐ and low‐temperature ranges, showing effective activation energies ( E a / k ).…”

Section: Heterocyclic Nitrogen‐centered Radicalsmentioning

confidence: 99%

Section: Triphenyl Imidazolyl Radicalsmentioning

confidence: 99%

Neutral Stable Nitrogen‐Centered Radicals: Structure, Properties, and Recent Functional Application Progress

Gao

2023

Adv Funct Materials

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Persistent and stable nitrogen‐centered organic radicals, including non‐heterocyclic/heterocyclic nitrogen‐centered radicals and nitrogen‐centered radical complexes, have attracted much attention due to their special multiple physical properties. Up to now, numerous nitrogen‐centered radical materials have been developed and applied as functional materials in magnetic, electronic, optical, and biologic fields. This review aims to discuss their structural features, physical properties, and recent progress in materials applications. Finally, an outlook providing inspiration for the future development is given.

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“…The prototypical benzo[ e ][1,2,4]triazin-4-yl, known as the Blatter radical (Figure ), and its derivatives exhibit exceptional air and moisture stability, extended spin delocalization, and attractive electrochemical , and photophysical − properties. These features lead to their exploration in molecular electronics and spintronics, , organic batteries, sensors, surface chemistry, controlled polymerization, , metal–organic frameworks, and photoconductive liquid crystals. − …”

Section: Introductionmentioning

confidence: 99%

“Upper” Ring Expansion of the Planar Blatter Radical via Photocyclization: Limitations and Impact on the Electronic Structure

et al. 2022

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Photocyclization of 8-aryloxybenzo[e][1,2,4]triazines leads to the formation of π-expanded flat Blatter radicals for three phenanthryloxy and pyren-1-yloxy derivatives, whereas no photoreaction is observed for the perylen-3-yloxy precursor. Two of the new radicals are nonplanar, out of which one is unstable to isolation. The radical with the fused pyrene ring constitutes the largest thus far paramagnetic polycyclic π-system containing seven fused rings with 27 sp2-hybridized atoms and 29 π-delocalized electrons. The investigation of the reaction conditions demonstrated the higher efficiency of photoformation of the parent radical in polar solvents, which suggests a polar transition state and the S1 photoreactive state. The effect of π expansion on the electronic structure was investigated with spectroscopic (UV–vis, electron paramagnetic resonance) and electrochemical methods augmented with density functional theory computational studies. The molecular structure of one of the radicals was determined with a single-crystal X-ray diffraction method.

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Axially Chiral Stable Radicals: Resolution and Characterization of Blatter Radical Atropisomers

Cited by 8 publications

References 49 publications

3-Substituted Blatter Radicals: Cyclization of N-Arylguanidines and N-Arylamidines to Benzo[e][1,2,4]triazines and PhLi Addition

3-Substituted Blatter Radicals: Cyclization of N-Arylguanidines and N-Arylamidines to Benzo[e][1,2,4]triazines and PhLi Addition

Neutral Stable Nitrogen‐Centered Radicals: Structure, Properties, and Recent Functional Application Progress

“Upper” Ring Expansion of the Planar Blatter Radical via Photocyclization: Limitations and Impact on the Electronic Structure

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