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Tailoring π-conjugation and vibrational modes to steer on-surface synthesis of pentalene-bridged ladder polymers

Author

Listed:
  • Bruno de la Torre

    (Palacký University
    Institute of Physics, The Czech Academy of Sciences)

  • Adam Matěj

    (Palacký University
    Institute of Physics, The Czech Academy of Sciences)

  • Ana Sánchez-Grande

    (IMDEA Nanociencia, C/ Faraday 9, Ciudad Universitaria de Cantoblanco)

  • Borja Cirera

    (IMDEA Nanociencia, C/ Faraday 9, Ciudad Universitaria de Cantoblanco)

  • Benjamin Mallada

    (Palacký University
    Institute of Physics, The Czech Academy of Sciences)

  • Eider Rodríguez-Sánchez

    (IMDEA Nanociencia, C/ Faraday 9, Ciudad Universitaria de Cantoblanco)

  • José Santos

    (IMDEA Nanociencia, C/ Faraday 9, Ciudad Universitaria de Cantoblanco
    Universidad Complutense)

  • Jesús I. Mendieta-Moreno

    (Institute of Physics, The Czech Academy of Sciences)

  • Shayan Edalatmanesh

    (Palacký University
    Institute of Physics, The Czech Academy of Sciences)

  • Koen Lauwaet

    (IMDEA Nanociencia, C/ Faraday 9, Ciudad Universitaria de Cantoblanco)

  • Michal Otyepka

    (Palacký University)

  • Miroslav Medveď

    (Palacký University)

  • Álvaro Buendía

    (Universidad Autónoma de Madrid, Cantoblanco)

  • Rodolfo Miranda

    (IMDEA Nanociencia, C/ Faraday 9, Ciudad Universitaria de Cantoblanco
    Universidad Autónoma de Madrid, Cantoblanco)

  • Nazario Martín

    (IMDEA Nanociencia, C/ Faraday 9, Ciudad Universitaria de Cantoblanco
    Universidad Complutense)

  • Pavel Jelínek

    (Palacký University
    Institute of Physics, The Czech Academy of Sciences)

  • David Écija

    (IMDEA Nanociencia, C/ Faraday 9, Ciudad Universitaria de Cantoblanco)

Abstract

The development of synthetic strategies to engineer π-conjugated polymers is of paramount importance in modern chemistry and materials science. Here we introduce a synthetic protocol based on the search for specific vibrational modes through an appropriate tailoring of the π-conjugation of the precursors, in order to increase the attempt frequency of a chemical reaction. First, we design a 1D π-conjugated polymer on Au(111), which is based on bisanthene monomers linked by cumulene bridges that tune specific vibrational modes. In a second step, upon further annealing, such vibrational modes steer the twofold cyclization reaction between adjacent bisanthene moieties, which gives rise to a long pentalene-bridged conjugated ladder polymer featuring a low bandgap. In addition, high resolution atomic force microscopy allows us to identify by atomistic insights the resonance form of the polymer, thus confirming the validity of the Glidewell and Lloyd´s rules for aromaticity. This on-surface synthetic strategy may stimulate exploiting previously precluded reactions towards π-conjugated polymers with specific structures and properties.

Suggested Citation

  • Bruno de la Torre & Adam Matěj & Ana Sánchez-Grande & Borja Cirera & Benjamin Mallada & Eider Rodríguez-Sánchez & José Santos & Jesús I. Mendieta-Moreno & Shayan Edalatmanesh & Koen Lauwaet & Michal O, 2020. "Tailoring π-conjugation and vibrational modes to steer on-surface synthesis of pentalene-bridged ladder polymers," Nature Communications, Nature, vol. 11(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:11:y:2020:i:1:d:10.1038_s41467-020-18371-2
    DOI: 10.1038/s41467-020-18371-2
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    Cited by:

    1. Deng-Yuan Li & Zheng-Yang Huang & Li-Xia Kang & Bing-Xin Wang & Jian-Hui Fu & Ying Wang & Guang-Yan Xing & Yan Zhao & Xin-Yu Zhang & Pei-Nian Liu, 2024. "Room-temperature selective cyclodehydrogenation on Au(111) via radical addition of open-shell resonance structures," Nature Communications, Nature, vol. 15(1), pages 1-10, December.

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