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The development of synthetic strategies to engineer \pi-conjugated polymersis of paramount importance in modern chemistry and materials science. Here weintroduce a theoretical and experimental synthetic paradigm based on the searchfor specific vibrational modes through an appropriate tailoring of the\pi-conjugation of the precursors, in order to increase the attempt frequencyof a chemical reaction. First, we on-surface design a 1D \pi-conjugated polymerwith specific \pi-topology, which is based on bisanthene monomers linked bycumulene bridges that tune specific vibrational modes. In a second step, uponfurther annealing, such vibrational modes steer the two-fold cyclizationreaction between adjacent bisanthene moieties, which gives rise to a long andfree-defect pentalene-bridged conjugated ladder polymer featuring a low bandgap. In addition, high resolution atomic force microscopy allows us to identifyby atomistic insights the resonant form of the polymer, thus confirming thevalidity of the Glidewell and Lloyd's rules for aromaticity. This on-surfacesynthetic strategy may stimulate exploiting previously precluded reactionstowards novel pi-conjugated polymers with specific structures and properties.

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