{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Grau BW"],"funding":["Deutsche Forschungsgemeinschaft","Solar Technologies go Hybrid"],"pagination":["22307-22314"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC8518863"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["60(41)"],"pubmed_abstract":["Hexaarylbenzene (HAB) derivatives are versatile aromatic systems playing a significant role as chromophores, liquid crystalline materials, molecular receptors, molecular-scale devices, organic light-emitting diodes and candidates for organic electronics. Statistical synthesis of simple symmetrical HABs is known via cyclotrimerization or Diels-Alder reactions. By contrast, the synthesis of more complex, asymmetrical systems, and without involvement of statistical steps, remains an unsolved problem. Here we present a generally applicable synthetic strategy to access asymmetrical HAB via an atom-economical and high-yielding metal-free four-step domino reaction using nitrostyrenes and α,α-dicyanoolefins as easily available starting materials. Resulting domino product-functionalized triarylbenzene (TAB)-can be used as a key starting compound to furnish asymmetrically substituted hexaarylbenzenes in high overall yield and without involvement of statistical steps. This straightforward domino process represents a distinct approach to create diverse and still unexplored HAB scaffolds, containing six different aromatic rings around central benzene core."],"journal":["Angewandte Chemie (International ed. in English)"],"pubmed_title":["Four-Step Domino Reaction Enables Fully Controlled Non-Statistical Synthesis of Hexaarylbenzene with Six Different Aryl Groups*."],"pmcid":["PMC8518863"],"funding_grant_id":["TS87/17-1","SFB953, grant Nr. 182849149","TS87/23-1"],"pubmed_authors":["Dill M","Tsogoeva SB","Hampel F","Jux N","Grau BW","Kahnt A"],"additional_accession":[]},"is_claimable":false,"name":"Four-Step Domino Reaction Enables Fully Controlled Non-Statistical Synthesis of Hexaarylbenzene with Six Different Aryl Groups*.","description":"Hexaarylbenzene (HAB) derivatives are versatile aromatic systems playing a significant role as chromophores, liquid crystalline materials, molecular receptors, molecular-scale devices, organic light-emitting diodes and candidates for organic electronics. Statistical synthesis of simple symmetrical HABs is known via cyclotrimerization or Diels-Alder reactions. By contrast, the synthesis of more complex, asymmetrical systems, and without involvement of statistical steps, remains an unsolved problem. Here we present a generally applicable synthetic strategy to access asymmetrical HAB via an atom-economical and high-yielding metal-free four-step domino reaction using nitrostyrenes and α,α-dicyanoolefins as easily available starting materials. Resulting domino product-functionalized triarylbenzene (TAB)-can be used as a key starting compound to furnish asymmetrically substituted hexaarylbenzenes in high overall yield and without involvement of statistical steps. This straightforward domino process represents a distinct approach to create diverse and still unexplored HAB scaffolds, containing six different aromatic rings around central benzene core.","dates":{"release":"2021-01-01T00:00:00Z","publication":"2021 Oct","modification":"2025-04-04T08:33:45.779Z","creation":"2025-04-04T08:33:45.779Z"},"accession":"S-EPMC8518863","cross_references":{"pubmed":["34060211"],"doi":["10.1002/anie.202104437"]}}