Issue 24, 2021

NIR absorbing aromatic (antiaromatic) vinylogous carbasapphyrins (3.3.1.0.1) with built-in fused dipolar aromatic hydrocarbon: synthesis and characterization

Abstract

Expedient syntheses, spectroscopic, solid state structural proof and theoretical study of three structural variants (with planar geometry) of strongly aromatic (antiaromatic) hybrid [26]/[24] vinylogous carbasapphyrins (3.3.1.0.1) exhibiting strong NIR absorption are reported. The azulene transformations within the macrocycles leading to aromaticity (antiaromaticity) have been supported by DFT based theoretical investigations. Intriguingly, the nature of macrocycles with the (lack of) aromaticity of the related carbaporphyrinoids has been anticipated to be fully triggered by the type of chemically functionalized thiophene based precursor.

Graphical abstract: NIR absorbing aromatic (antiaromatic) vinylogous carbasapphyrins (3.3.1.0.1) with built-in fused dipolar aromatic hydrocarbon: synthesis and characterization

Supplementary files

Article information

Article type
Research Article
Submitted
01 Sep 2021
Accepted
22 Oct 2021
First published
25 Oct 2021

Org. Chem. Front., 2021,8, 6909-6915

NIR absorbing aromatic (antiaromatic) vinylogous carbasapphyrins (3.3.1.0.1) with built-in fused dipolar aromatic hydrocarbon: synthesis and characterization

S. Sahoo, G. Velmurugan, B. Chakraborty, P. Comba and H. Rath, Org. Chem. Front., 2021, 8, 6909 DOI: 10.1039/D1QO01247A

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