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

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 Otyepka, Miroslav Medveď, Álvaro Buendía, Rodolfo Miranda, Nazario Martín (), Pavel Jelínek () and David Écija ()
Additional contact information
Bruno de la Torre: Palacký University
Adam Matěj: Palacký University
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
Eider Rodríguez-Sánchez: IMDEA Nanociencia, C/ Faraday 9, Ciudad Universitaria de Cantoblanco
José Santos: IMDEA Nanociencia, C/ Faraday 9, Ciudad Universitaria de Cantoblanco
Jesús I. Mendieta-Moreno: Institute of Physics, The Czech Academy of Sciences
Shayan Edalatmanesh: Palacký University
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
Nazario Martín: IMDEA Nanociencia, C/ Faraday 9, Ciudad Universitaria de Cantoblanco
Pavel Jelínek: Palacký University
David Écija: IMDEA Nanociencia, C/ Faraday 9, Ciudad Universitaria de Cantoblanco

Nature Communications, 2020, vol. 11, issue 1, 1-8

Abstract: 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.

Date: 2020
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DOI: 10.1038/s41467-020-18371-2

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