Chromium aminocarbenes tethered to dienes of all three electronic natures undergo an efficient intramolecular (4 + 1)-cycloaddition to give N-heteropolycyclic compounds. Ligands on chromium had a profound effect on the course of the reaction.
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http://dx.doi.org/10.1021/ol4025887 | DOI Listing |
Org Lett
January 2025
Department of Organic Chemistry, College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. China.
A Cu-catalyzed relay process for the preparation of diazidated quinazolinone and polycyclic imidazole derivatives in which readily available alkene-tethered substrates undergo an addition/cyclization/C(sp)-H functionalization of alkene sequences with high efficiency is described. Various functionalized N-heteropolycyclic compounds were readily prepared in good yields with a broad substrate scope. Moreover, the direct azidation of the α-C(sp)-H bond of the corresponding N-heterocycles has been demonstrated on the basis of mechanistic studies, which provide an alternative late-stage functionalization approach for the derivatization of N-heterocyclic scaffolds.
View Article and Find Full Text PDFChemistry
December 2024
Inorganic Chemistry, Ruprecht-Karls Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
Phys Chem Chem Phys
February 2022
Physikalisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 253, 69120 Heidelberg, Germany.
N-Heteropolycyclic aromatic compounds are promising organic semiconductors for applications in field effect transistors and solar cells. Thereby the electronic structure of organic/metal interfaces and thin films is essential for the performance of organic-molecule-based devices. Here, we studied the structural and the electronic properties of 6,7,12,13-tetraazapentacene (TAP) adsorbed on Au(111) using vibrational and electronic high-resolution electron energy loss spectroscopy in combination with state-of-the-art quantum chemical calculations.
View Article and Find Full Text PDFJ Phys Chem C Nanomater Interfaces
September 2021
Physikalisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 253, D-69120 Heidelberg, Germany.
N-heteropolycyclic aromatic compounds are promising organic electron-transporting semiconductors for applications in field-effect transistors. Here, we investigated the electronic properties of 1,3,8,10-tetraazaperopyrene derivatives adsorbed on Au(111) using a complementary experimental approach, namely, scanning tunneling spectroscopy and two-photon photoemission combined with state-of-the-art density functional theory. We find signatures of weak physisorption of the molecular layers, such as the absence of charge transfer, a nearly unperturbed surface state, and an intact herringbone reconstruction underneath the molecular layer.
View Article and Find Full Text PDFJ Phys Chem Lett
January 2021
Ruprecht-Karls-Universität Heidelberg, Physikalisch-Chemisches Institut, Im Neuenheimer Feld 253, 69120 Heidelberg, Germany.
Efficient charge injection at organic semiconductor/metal interfaces is crucial for the performance of organic field effect transistors. Interfacial hybrid band formation between electronic states of the organic compound and the metal electrode facilitates effective charge injection. Here, we show that a long-range ordered monolayer of a flat-lying N-heteropolycyclic aromatic compound on Au(111) leads to dispersing occupied and unoccupied interfacial hybrid bands.
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