biostudies-literatureVicent DJEuropean Research CouncilComunidad de MadridAgencia Estatal de InvestigaciónJunta de AndalucíaGeneralitat Valenciana10112-10120https://www.ebi.ac.uk/biostudies/studies/S-EPMC10530488biostudies-literatureUnknown14(37)Despite their great potential as molecular building blocks for organic synthesis, tetrabromo-p-quinodimethanes (TBQs) are a relatively unknown family of compounds. Herein, we showcase a series of five derivatives incorporating two tetrabromo-anthraquinodimethane (TBAQ) units linked by π-conjugated spacers of different nature and length. The resulting dimers TBQ1-5 are fully characterised by means of thorough spectroscopic measurements and theoretical calculations. Interestingly, owing to the steric hindrance imposed by the four bulky bromine atoms, the TBAQ fragments adopt a characteristically warped geometry, somehow resemblant of a butterfly, and the novel dimers show a complex NMR pattern with signal splittings. To ascertain whether dynamic processes regarding fluxional inversionChemical scienceDimeric tetrabromo-p-quinodimethanes: synthesis and structural/electronic properties.PMC10530488MFA/2022/017PID2021-127127NB-I00TED2021-131255B-C44PROYEXCEL-0328PID2019-108532GB-I00PROMETEO/2020/077PID2021-128569NB-I00PID2020-119748GA-I00PRE2021-097082PID2020-114653RB-I00951224Y2018/NMT-4783Urgel JIEcija DCalbo JVicent DJOrti EMartin NPerez-Escribano MBarragan ASantos JCardenas-Valdivia ACasado JfalseDimeric tetrabromo-p-quinodimethanes: synthesis and structural/electronic properties.Despite their great potential as molecular building blocks for organic synthesis, tetrabromo-p-quinodimethanes (TBQs) are a relatively unknown family of compounds. Herein, we showcase a series of five derivatives incorporating two tetrabromo-anthraquinodimethane (TBAQ) units linked by π-conjugated spacers of different nature and length. The resulting dimers TBQ1-5 are fully characterised by means of thorough spectroscopic measurements and theoretical calculations. Interestingly, owing to the steric hindrance imposed by the four bulky bromine atoms, the TBAQ fragments adopt a characteristically warped geometry, somehow resemblant of a butterfly, and the novel dimers show a complex NMR pattern with signal splittings. To ascertain whether dynamic processes regarding fluxional inversion2023-01-01T00:00:00Z2023 Sep2026-05-29T02:05:27.408Z2025-02-19T04:07:00.074ZS-EPMC105304883777212310.1039/d3sc01615c