Download file (11.7 MB)
Download as zip (10.3 MB)

Collection

Citation

Description:

Pyrazinacenes are linearly fused heteroaromatic rings, with N atoms replacing all apical CH moieties. Component rings may exist in a reduced state, having NH groups instead of N, causing cross-conjugation. These compounds have interesting optical and electronic properties, including strong fluorescence in the near-infrared region and photocatalytic properties, leading to diverse possible applications in bio-imaging and organic synthesis, as well as obvious molecular electronic uses. In this study, we investigated the behavior of seven-ring pyrazinacene 2,3,11,12-tetraphenyl-7,16-dihydro-1,4,5,6,7,8,9,12,13,14,15,16,17,18-tetradecaazaheptacene (Ph4H2N14HEPT), with an emphasis on protic processes, including oxidation, tautomerism, deprotonation, and protonation, and the species resulting from those processes. We used computational methods to optimize the structures of the different species and generate/compare molecular orbital structures. The aromaticity of the species generated by the different processes was assessed using the nucleus-independent chemical shifts, and trends in the values were associated with the different transformations of the pyrazinacene core. The computational data were compared with experimental data obtained from synthetic samples of the molecule tBu8Ph4H2N14HEPT.

Rights:

• Creative Commons BY Attribution 4.0 International
  

Keyword: pyrazinacene; acene; N-heteroacene; azaacene; tautomerization

Date published: 2024-05-20

Publisher: MDPI AG

Journal:

• Molecules (ISSN: 14203049) vol. 29 issue. 10 2407

Funding:

• GENCI A0050807367

Manuscript type: Publisher's version (Version of record)

MDR DOI:

First published URL: https://doi.org/10.3390/molecules29102407

Related item:

Other identifier(s):

Contact agent:

Updated at: 2024-11-13 16:30:41 +0900

Published on MDR: 2024-11-13 16:30:41 +0900