Gem-Dibromovinylenes: Highly Versatile Systems for On-Surface Synthesis

The advent of the so-called On-Surface synthesis represents a new scenario where testing new reaction conditions affording disruptive materials impossible to be obtained by conventional synthetic chemistry. In this regard, we have reported an unprecedented chemical reaction from tetrabromo- p -quinodimethanes (TBQs) which, by heating on gold surface, has allowed to obtain a variety of new 1D π-conjugated polymers,[1] some of them exhibiting a quasimetallic behavior.[2] In this presentation, new designed organic molecules endowed with gem-dibromovinylene units have been synthesized with the aim of broadening the scope of this highly reactive functional group to other on-surface chemical reactions.[3] Thus, new different polymers or molecular systems will be presented and discussed.[4] References [1] A. Sánchez-Grande, et al., "On-surface synthesis of ethynylene bridged anthracene polymers", Angew. Chem. Int. Ed. , 2019 , 58 , 6559-6563. [2] Cirera, B., et al., “Tailoring topological order and π-conjugation to engineer quasi-metallic polymers”. Nat. Nanotechnol. 2020 , 15, 437–443. [3] Sánchez-Grande, et al., "Surface-assisted Synthesis of N-substituted π-Conjugated Polymers " Adv. Sci ., 2022 , - advs.202200407R1 [4] E. Pérez-Elvira, et al., "Generating Antiaromaticity: Thermally-selective Skeletal Rearrangements at Interfaces", Nat. Synth. , 2023 , NATSYNTH-22121246B.