Issue 6, 2023

On-surface synthesis of non-benzenoid conjugated polymers by selective atomic rearrangement of ethynylarenes

Abstract

Here, we report a new on-surface synthetic strategy to precisely introduce five-membered units into conjugated polymers from specifically designed precursor molecules that give rise to low-bandgap fulvalene-bridged bisanthene polymers. The selective formation of non-benzenoid units is finely controlled by the annealing parameters, which govern the initiation of atomic rearrangements that efficiently transform previously formed diethynyl bridges into fulvalene moieties. The atomically precise structures and electronic properties have been unmistakably characterized by STM, nc-AFM, and STS and the results are supported by DFT theoretical calculations. Interestingly, the fulvalene-bridged bisanthene polymers exhibit experimental narrow frontier electronic gaps of 1.2 eV on Au(111) with fully conjugated units. This on-surface synthetic strategy can potentially be extended to other conjugated polymers to tune their optoelectronic properties by integrating five-membered rings at precise sites.

Graphical abstract: On-surface synthesis of non-benzenoid conjugated polymers by selective atomic rearrangement of ethynylarenes

Supplementary files

Article information

Article type
Edge Article
Submitted
23 avq 2022
Accepted
19 dek 2022
First published
20 dek 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2023,14, 1403-1412

On-surface synthesis of non-benzenoid conjugated polymers by selective atomic rearrangement of ethynylarenes

A. Jiménez-Martín, F. Villalobos, B. Mallada, S. Edalatmanesh, A. Matěj, J. M. Cuerva, P. Jelínek, A. G. Campaña and B. de la Torre, Chem. Sci., 2023, 14, 1403 DOI: 10.1039/D2SC04722E

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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