Polycyclic aromatic azomethine ylides: a unique entry to extended polycyclic heteroaromatics
Literature Information
Publication Date
2014-10-22
DOI
10.1039/C4SC02793K
Impact Factor
9.825
Authors
Reinhard Berger, Manfred Wagner, Klaus Müllen
View Original
Abstract
Based on polycyclic aromatic azomethine ylides (PAMYs), a metal-free “cycloaddition-planarization-sequence” is proposed, providing a unique entry to extended nitrogen-containing polycyclic aromatic hydrocarbons (N-PAHs). This method is highly versatile, as the structure of unprecedented N-PAHs can be tailored by the dipolarophile in the crucial 1,3-cycloaddition-reaction. Linear, as well as five- and six-membered cyclic dipolarophiles are successfully used. The geometric and optoelectronic nature of N-PAHs are investigated by UV-vis absorption and single crystal structure analysis. Remarkably, the newly synthesized N-PAHs demonstrate varying absorption profiles, covering the whole visible light range with rich photophysical properties, for example, fluorescent quantum yields up to 54%.
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Source Journal
Chemical Science
CiteScore:
14.4
Self-citation Rate:
3.9%
Articles per Year:
1413
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Recommended Compounds
5-Amino-1-(2,4-difluorophenyl)-3-methyl-1H-pyrazole-4-carbonitrile
CAS Number:
1020057-92-4
Molecular Formula:
C11H8F2N4
![4-[(1-Methyl-1H-pyrrol-2-yl)methylene]-1,3(2H,4H)-isoquinolinedione structure](https://static.chemtradehub.com/structs/110/1104546-89-5-a600.webp "4-[(1-Methyl-1H-pyrrol-2-yl)methylene]-1,3(2H,4H)-isoquinolinedione structure")
4-[(1-Methyl-1H-pyrrol-2-yl)methylene]-1,3(2H,4H)-isoquinolinedione
CAS Number:
1104546-89-5
Molecular Formula:
C15H12N2O2
![2-(Methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole structure](https://static.chemtradehub.com/structs/122/1226781-80-1-09d5.webp "2-(Methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole structure")
2-(Methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole
CAS Number:
1226781-80-1
Molecular Formula:
C6H9N3O2S
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