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二茚并吡嗪:缺电子芳烃。

Diindenopyrazines: Electron-Deficient Arenes.

作者信息

Brosius Victor, Weigold Svenja, Hippchen Nikolai, Rominger Frank, Freudenberg Jan, Bunz Uwe H F

机构信息

Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

出版信息

Chemistry. 2021 Jul 12;27(39):10001-10005. doi: 10.1002/chem.202100372. Epub 2021 Jun 4.

DOI:10.1002/chem.202100372
PMID:33830516
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8361971/
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 cm  V  s .

摘要

报道了空气稳定的电子受体二茚并吡嗪4 a - g的合成、性质及应用,展示了在6位和12位引入功能性芳基。目标产物可在百毫克至克级规模上获得。4 a - g中芳基的结构调节了它们的溶解性、氧化还原电位和光学性质。将缺电子芳基引入缺电子的二茚并吡嗪主链可将电子亲和能降低至 -4 eV,使这些化合物作为n型半导体具有吸引力。4 e的一种简单有机场效应晶体管(未经优化)显示出电子传输,迁移率高达0.037 cm² V⁻¹ s⁻¹ 。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b14d/8361971/ea2a082c80cf/CHEM-27-10001-g008.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b14d/8361971/ea2a082c80cf/CHEM-27-10001-g008.jpg

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Synthesis of the Unknown Indeno[1,2-a]fluorene Regioisomer: Crystallographic Characterization of Its Dianion.
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