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Diindenopyrazines: Electron-Deficient Arenes.

ABSTRACT: The syntheses, properties and application of the air-stable electron acceptors, diindenopyrazines 4 a-g are reported demonstrating the introduction of functional aryl groups in the 6- and 12-positions. The targets are accessible on the hundred milligram to gram scale. The structure of the aryl groups in 4 a-g modulates their solubility, redox potentials and optical properties. The introduction of electron-poor aryl groups to the electron-poor diindenopyrazine backbone reduces the electron affinity to -4 eV, making the compounds attractive as n-semiconductors. A simple organic field-effect transistor of 4 e -without optimization- shows electron transport with a mobility of up to 0.037 cm² V^-1 s^-1 .

SUBMITTER: Brosius V

PROVIDER: S-EPMC8361971 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature

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Diindenopyrazines: Electron-Deficient Arenes.

Brosius Victor V Weigold Svenja S Hippchen Nikolai N Rominger Frank F Freudenberg Jan J Bunz Uwe H F UHF

Chemistry (Weinheim an der Bergstrasse, Germany) 20210604 39

The syntheses, properties and application of the air-stable electron acceptors, diindenopyrazines 4 a-g are reported demonstrating the introduction of functional aryl groups in the 6- and 12-positions. The targets are accessible on the hundred milligram to gram scale. The structure of the aryl groups in 4 a-g modulates their solubility, redox potentials and optical properties. The introduction of electron-poor aryl groups to the electron-poor diindenopyrazine backbone reduces the electron affini ...[more]

PMID: 33830516

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