Two-step synthesis of new fused systems based on [1,2,5]oxadiazolo[3,4-b]quinoxaline by a combination of the Scholl reaction and nucleophilic aromatic substitution of hydrogen (S_N^H)

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2024年6月1日

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E. M. Krynina,
Yu. A. Kvashnin,
D. A. Gazizov,
M. I. Kodess,
M. A. Ezhikova,
G. L. Rusinov,
E. V. Verbitskiy,
V. N. Charushin

摘要

A simple synthetic route to poorly available polycyclic systems with a [1,2,5]oxadiazolo-[3,4-b]quinoxaline backbone has been developed, which is based on the sequence of nucleophilic aromatic substitution of hydrogen and the Scholl cross-coupling. According to the data from electrochemical and photophysical measurements, the synthesized compounds can be potentially considered as the narrow-gap (from 1.97 to 2.34 eV) n-type organic semiconductors, the energy levels of which are comparable to those of top commercially available electronic semiconductors.

Two-step synthesis of new fused systems based on [1,2,5]oxadiazolo[3,4-b]quinoxaline by a combination of the Scholl reaction and nucleophilic aromatic substitution of hydrogen (SNH)

摘要

Two-step synthesis of new fused systems based on [1,2,5]oxadiazolo[3,4-b]quinoxaline by a combination of the Scholl reaction and nucleophilic aromatic substitution of hydrogen (S_N^H)