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Meso-meso 1,3-Bis(E-vinyl)azulene bridged tetrathiaoctaphyrins: synthesis and spectroscopic and theoretical characterization

The expedient syntheses, spectroscopic analysis, solid state structural proof and theoretical study of structural variants of strongly aromatic(antiaromatic) meso-meso 1,3-bis(E-vinyl)azulene bridged(nonbridged) tetrathiaoctaphyrins exhibiting strong NIR absorption are reported. The lack of particip...

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Bibliographic Details
Main Authors: Sahoo, Sumit (Author) , Velmurugan, Gunasekaran (Author) , Comba, Peter (Author) , Rath, Harapriya (Author)
Format: Article (Journal)
Language:English
Published: 2023
In: Organic chemistry frontiers
Year: 2023, Volume: 10, Issue: 22, Pages: 5601-5609
ISSN:2052-4129
DOI:10.1039/D3QO01131C
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1039/D3QO01131C
Verlag, lizenzpflichtig, Volltext: https://pubs.rsc.org/en/content/articlelanding/2023/qo/d3qo01131c
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Author Notes:Sumit Sahoo, Gunasekaran Velmurugan, Peter Comba and Harapriya Rath
Description
Summary:The expedient syntheses, spectroscopic analysis, solid state structural proof and theoretical study of structural variants of strongly aromatic(antiaromatic) meso-meso 1,3-bis(E-vinyl)azulene bridged(nonbridged) tetrathiaoctaphyrins exhibiting strong NIR absorption are reported. The lack of participation of the 1,3-bis(E-vinyl)azulene internal bridge in the global π-conjugated network of tetrathiaoctaphyrins led to the loss of effective dual macrocyclic conjugation pathways, which has been fully supported by thorough DFT studies. AICD, NICS, HOMA, MCI, AV1245 index, AVmin, WBI and ELF analyses have been carried out to explain the nature and origin of the major [34π]/[36π] single-conjugated Hückel aromaticity(antiaromaticity) in detail for all the three octaphyrins with(without) the meso-meso 1,3-bis(E-vinyl)azulene bridge.
Item Description:Online veröffentlicht: 22. September 2023
Gesehen am 24.11.2023
Physical Description:Online Resource
ISSN:2052-4129
DOI:10.1039/D3QO01131C

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