Donor- and acceptor-functionalized dibenzo[a,e]pentalenes: modulation of the electronic band gap
Donor- and acceptor-functionalized dibenzo[a,e]pentalenes: modulation of the electronic band gap
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DOI：
10.1039/c6qo00487c
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发表时间：
2017-05
影响因子：
5.4
通讯作者：
J. Wilbuer;David C. Grenz;G. Schnakenburg;Birgit Esser
中科院分区：
文献类型：
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作者：
J. Wilbuer;David C. Grenz;G. Schnakenburg;Birgit Esser
二苯并[a，e]戊二烯(DBP)是一种低禁带有机半导体。描述了一种合成DBP的通用路线，该路线在5，10-位上用芳基或烷基取代，在2，7-位上给电子或接受电子官能团。合成了6个给体或受体功能化的DBP衍生物，它们具有两性氧化还原行为和约2 eV的带隙。通过选择2，7-取代基，HOMO/LUMO能级和带隙可以在高达0.6 eV的范围内调节。在固体状态下，DBP衍生物呈人字形堆积结构。
Dibenzo[a,e]pentalene (DBP) is a low-bandgap organic semiconductor. A versatile synthetic route to DBPs substituted with aryl or alkyl groups in the 5,10-positions and electron-donating or -accepting functionalities in the 2,7-positions is described. Six donor- or acceptor-functionalized DBP derivatives were synthesized that show amphoteric redox behavior and band gaps around 2 eV. Through choice of the 2,7-substituents, the HOMO/LUMO energy levels and band gaps can be adjusted within a range of up to 0.6 eV. In the solid state, the DBP derivatives assume herringbone-type packing structures.