On-Surface Synthesis of Indenofluorene Polymers by Oxidative Five-Membered Ring Formation

Journal of the American Chemical Society
Marco Di GiovannantonioRoman Fasel

Abstract

On-surface synthesis is a successful approach to the creation of carbon-based nanostructures that cannot be obtained via standard solution chemistry. In this framework, we have established a novel synthetic pathway to one-dimensional conjugated polymers composed of indenofluorene units. Our concept is based on the use of ortho-methyl groups on a poly( para-phenylene) backbone. In this situation, surface-assisted oxidative ring closure between a methyl and the neighboring aryl moiety gives rise to a five-membered ring. The atomically precise structures and electronic properties of the obtained indenofluorene polymers have been unambiguously characterized by STM, nc-AFM, and STS, supported by theoretical calculations. This unprecedented synthetic protocol can potentially be extended to other polyphenylenes and eventually graphene nanoribbons, to incorporate five-membered rings at desired positions for the fine-tuning of electronic properties.

Citations

Jul 31, 2019·Angewandte Chemie·Jindong RenNikos L Doltsinis
Jan 16, 2020·Chemical Communications : Chem Comm·Xin YuWei Xu
Jul 26, 2019·Angewandte Chemie·Marek GrzybowskiDaniel T Gryko
May 14, 2019·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Faming Kang, Wei Xu
Jul 30, 2019·Frontiers in Chemistry·Dorothea GolzePatrick Rinke
May 16, 2019·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·José I UrgelRoman Fasel
Jun 25, 2021·Chemical Science·Ana Cristina Gómez-HerreroJohann Coraux
Jul 10, 2021·Chemical Communications : Chem Comm·Cristina Martín-FuentesDavid Écija
May 20, 2020·Journal of the American Chemical Society·Ian Cheng-Yi HouKlaus Müllen
Jan 15, 2020·Journal of the American Chemical Society·Marco Di GiovannantonioKlaus Müllen
Jul 8, 2020·The Journal of Physical Chemistry Letters·Tao WangJunfa Zhu
Jul 10, 2020·Journal of the American Chemical Society·Peter H JacobseMichael F Crommie
Dec 23, 2020·The Journal of Physical Chemistry Letters·Ana Sánchez-GrandeDavid Écija
Jul 15, 2020·Journal of the American Chemical Society·Marco Di GiovannantonioRoman Fasel
Jul 17, 2019·Journal of the American Chemical Society·Marco Di GiovannantonioRoman Fasel
Nov 6, 2018·ACS Nano·Shantanu MishraRoman Fasel

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