Protic Processes in an Extended Pyrazinacene: The Case of Dihydrotetradecaazaheptacene - INSA Rennes - Institut National des Sciences Appliquées de Rennes Access content directly
Journal Articles Molecules Year : 2024

Protic Processes in an Extended Pyrazinacene: The Case of Dihydrotetradecaazaheptacene

Abstract

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.
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hal-04614260 , version 1 (17-06-2024)

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Aël Cador, Samia Kahlal, Gary J Richards, Jean-François Halet, Jonathan P Hill. Protic Processes in an Extended Pyrazinacene: The Case of Dihydrotetradecaazaheptacene. Molecules, 2024, 29 (10), pp.2407. ⟨10.3390/molecules29102407⟩. ⟨hal-04614260⟩
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