Dibenzo[a,e]pentalenes with Low-Lying LUMO Energy Levels as Potential n-Type Materials

Autor:	David C. Grenz, Maximilian Schmidt, Daniel Kratzert, Birgit Esser
Rok vydání:	2018
Předmět:	Diffraction Absorption spectroscopy 010405 organic chemistry Chemistry Band gap Ambipolar diffusion Organic Chemistry Time-dependent density functional theory 010402 general chemistry Photochemistry 01 natural sciences 0104 chemical sciences Organic semiconductor Cyclic voltammetry HOMO/LUMO
Zdroj:	The Journal of Organic Chemistry. 83:656-663
ISSN:	1520-6904 0022-3263
Popis:	Ambipolar organic semiconductors are of high interest for organic field-effect transistors. For n-type conduction, low LUMO energies are required. Dibenzo[a,e]pentalenes (DBPs) are promising compounds; however, few derivatives exist with energetically low-lying LUMO levels. Here, we present DBP derivatives with LUMO energies down to -3.73 eV and small bandgaps down to 1.63 eV determined through cyclic voltammetry, UV/vis absorption spectroscopy, and TDDFT calculations. Single-crystal X-ray diffraction analysis revealed a 1D π-stacking mode. The addition of arylalkynyl substituents at the five-membered rings in a facile and versatile synthetic route allowed for tuning of the band gaps and LUMO energies. The synthetic route can easily be modified to access a variety of DBP derivatives. The LUMO energies of the DBP derivatives presented herein make them attractive for an application in n-type or ambipolar field-effect transistors.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::d03cf32bbdbca7bb035ef2eebe359bc4 https://doi.org/10.1021/acs.joc.7b02250 Zobrazit plný text záznamu