Issue 11, 2023

Single-molecule conductance studies on quasi- and metallaaromatic dibenzoylmethane coordination compounds and their aromatic analogs

Abstract

The ability to predict the conductive behaviour of molecules, connected to macroscopic electrodes, represents a crucial prerequisite for the design of nanoscale electronic devices. In this work, we investigate whether the notion of a negative relation between conductance and aromaticity (the so-called NRCA rule) also pertains to quasi-aromatic and metallaaromatic chelates derived from dibenzoylmethane (DBM) and Lewis acids (LAs) that either do or do not contribute two extra dπ electrons to the central resonance-stabilised β-ketoenolate binding pocket. We therefore synthesised a family of methylthio-functionalised DBM coordination compounds and subjected them, along with their truly aromatic terphenyl and 4,6-diphenylpyrimidine congeners, to scanning tunneling microscope break-junction (STM-BJ) experiments on gold nanoelectrodes. All molecules share the common motif of three π-conjugated, six-membered, planar rings with a meta-configuration at the central ring. According to our results, their molecular conductances fall within a factor of ca. 9 in an ordering aromatic < metallaaromatic < quasi-aromatic. The experimental trends are rationalised by quantum transport calculations based on density functional theory (DFT).

Graphical abstract: Single-molecule conductance studies on quasi- and metallaaromatic dibenzoylmethane coordination compounds and their aromatic analogs

Supplementary files

Article information

Article type
Paper
Submitted
12 Oct 2022
Accepted
13 Feb 2023
First published
14 Feb 2023
This article is Open Access
Creative Commons BY-NC license

Nanoscale, 2023,15, 5305-5316

Single-molecule conductance studies on quasi- and metallaaromatic dibenzoylmethane coordination compounds and their aromatic analogs

A. Mang, N. Rotthowe, K. Beltako, M. Linseis, F. Pauly and R. F. Winter, Nanoscale, 2023, 15, 5305 DOI: 10.1039/D2NR05670D

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