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On-Surface Synthesis of Oligo(indenoindene)

Cite this: J. Am. Chem. Soc. 2020, 142, 30, 12925–12929
Publication Date (Web):July 14, 2020
https://doi.org/10.1021/jacs.0c05701
Copyright © 2020 American Chemical Society

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    Abstract

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    Fully conjugated ladder polymers (CLP) possess unique optical and electronic properties and are considered promising materials for applications in (opto)electronic devices. Poly(indenoindene) is a CLP consisting of an alternating array of five- and six-membered rings, which has remained elusive so far. Here, we report an on-surface synthesis of oligo(indenoindene) on Au(111). Its structure and a low electronic band gap have been elucidated by low-temperature scanning tunneling microscopy and spectroscopy and noncontact atomic force microscopy, complemented by density functional theory calculations. Achieving defect-free segments of oligo(indenoindene) offers exclusive insight into this CLP and provides the basis to further synthetic approaches.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.0c05701.

    • Crystallographic data for 1 (CIF)

    • Synthesis of the molecular precursor 1; experimental and theoretical methods; additional experimental and theoretical results (PDF)

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